Lucky Number 5

I treated this one differently from most men I have ever dated. I didn’t tell a single soul about him until after our third date. I had this ridiculous idea that if I could just nurture it and protect this budding relationship it would be safe. I told myself that telling people about it was too risky and that all I had to do was make it to 5 dates and then I could tell everyone.

Date 1

We talked for ages on Hinge during lockdown. He proposed a zoom chat, but with my then 8 hours of daily zoom time, I said we would just wait it out. We met up in Spitalfields Market on July first. Since bars weren’t scheduled to open until 2 days later, this was the best option. My first impression wasn’t ideal. He didn’t really look like his photos. He showed up wearing shorts, a sweatshirt, and flip flops and the omnipresent hair, he immediately apologised for both the outfit and hair. I was pretty nervous the first ten minutes, but he was so genuine and earnest that I felt pretty at ease. He has one of those smiles where his whole face crinkles and it made him seem so sweet. I could tell he thought I was pretty, and alluded to it in the classic British way. It made me feel excited. It was my first real DATE DATE after months of being alone. We ended up sitting in the empty market for 4 hours and two bottles of wine. It was really lovely. He blew me a kiss when he left and I thought what a cute, goofy man. I hope I see him soon.

We texted every day after that.

Date 2

The Narrow, London

Four our second date I ventured over to his neighborhood for a date in a proper restaurant! He dressed much nicer this time around and even had a fresh hair cut. He also wore boat shoes…aka my greatest weakness in life. We sat outside overlooking the river. It’s so easy to talk him, there;s never been a moment of awkwardness, and he was good at asking questions so I felt like we were really getting to know each other. After the date he walked me to the uber and kissed me. Usually I text all my friends in shock after a good date, but I kept telling myself, just make it to 5 dates. Don’t embarrass yourself, don’t jinx it. I just kept thinking to myself, thisisspecial thisisspecial thisispecial.

Date 3

Bottles, London

Our third date was in a romantic wine bar. At this point, I already knew I was falling for him. He made sure to tell me how good I looked and how he loved how I did my hair. Two bottles of wine later, we were for sure making out at the bar. DEFINITELY not my usual behaviour. I hate PDA, but in the moment everything was just so romantic and I wasn’t being my usual control freak. I am not used to a man being so overtly interested in me and clear about his attraction to me. Let’s be honest, my love language is words of affirmation, so I was hanging on every word

He texted me the next morning that he was still thinking about how good I looked, if that’s not a great way to start your day, I don’t know what is.

A few days later I went away to the countryside for some R&R. He was actually visiting a nearby town that weekend. We talked the whole time. Right before I went back to the city I did a cursory instagram stalk. Where I saw he had tagged a girl in his weekend post…I felt that immediate pang in my stomach.

But I tried to remain calm. There was no reason to panic. He had sent me photos of the trip, and told me he missed me. No chance he was doing this while he was away with a girl. I was over reacting, and what I could even say anyway. At this point, I decided to ignore it and keep talking to him as if everything was ok.

Date 4

Chez Moi.

This was my favourite date. It felt like we were actually together. After texting every day for 5 weeks, I felt like we were past all the getting-to-know -you chat and actually had things to talk about. We talked about family, I told me how it was killing me to be so far from everyone I love. We talked about his past relationships. I finally just said to him,

I really like spending time with you.

Sounds trivial, but for me, being open and honest about liking someone is extremely hard for me. I constantly live in fear of rejection. But he smiled and said, Awwww, I like spending time with you. I said to him, I really don’t want to get hurt in this. But he said he appreciated how sweet and open I was being with him. We discovered that his love language is quality time, so for several hours we just sat on the couch together and talked, no distractions. It was actually perfect. Not to mention, look at the bomb cheese plate I made

He didnt spend the night, but he left around 1 AM. I was so sad to see him go. I woke up thinking, I can almost tell people about him, I can’t wait.

Later that week, he went away on a guys trip so he was gone for a little while.

Except of course, it wasn’t. He posted another photo of the same girl. This time I knew there was no real way to ignore this. I wanted to immediately lash out and question him on the extensive lie he told me. But I kept it together. This time too, he sent me photos from the trip, told me he was bringing me back a pony and sent me various flirty messages.

The following week I was away at a girls trip and decided to test the water. I texted him asking if he missed me, he immediately replied, “very much so” and I said I wish you were here, he said “me too”. So for a few hours, I kept telling myself, shes just a friend. YOU ARE OK. You can fight for this. Not all hope is lost.

Unfortunately, several wines later I texted him again. In the past when I was outside the city he asked me to send him selfies so this was very much par for the course. And to be honest I am used to texting him

It felt like a punch in the stomach. Deep down, I knew it was done. That the brief moment where I felt secure and pretty and wanted was just a flash in the pan. But I want to know what happened so badly, had he been dating this girl the whole time? Had she asked him to be exclusive? Had he changed his mind? Did I do something wrong? Was I ever right that he liked me?

As you have seen in my past failures, not knowing is what makes me feel most unhinged. I tried so hard to give it some time, I texted him asking how being back home was. He responded immediately but not when I asked him if he wanted to do something this week. I waited a little while and sent this massively dramatic message.

Its been 4 hours and I never heard back. I don’s really expect to. I know it’s a sappy message but it’s how I feel. So so so so stupid.

The problem is, each time I bounce back from these rejections there is less of me left. The next time I want to tell a man I like him, I will remember this, and stop myself. It all chips away at me, and soon there will be truly nothing left. Everyone my life gives me so much shit for being pessimistic, but I don’t know how to push myself to keep doing this. Is this better than the feeling of being fully alone, I’m not so sure.

As they say, you have to keep going. So I did. Last night I went on one of the worst dates I’ve ever been on. I won’t even dignify it with a post. This man might be the last finance bro I ever go out with. The misogyny permeated from every inch of him, from his rolex through his loafers. He also let me know I was far too old to be this picky. (honestly, probably true). I couldn’t even cry after the date, I was so enraged.

Where were we…let’s catch up

So I figured it made sense to start a recap of all my dates in London. So you can all be up to date.

Date #1

I had been in London a few weeks before I went on my first date. I was still mourning leaving Chris behind, but that certainly didn’t stop be from perusing Hinge on an hourly basis.

My first date was with a VERY handsome British man at a VERY upscale bar. My first thought was, this is the London life. THIS WILL BE MY LAST FIRST DATE. If you have read my posts, you know I tend to skew the towards the insane. We had several drinks and pleasant banter, he is a business psychologist so plenty of material. (Yes, I did ask him if he was like Wendy on Billions). One thing to note, as you will see in upcoming stories, Brits don’t eat when they go out. They just drink. So I had 4 cocktails and….olives. Tough. I thought it had gone really well. But when the bill came, he suggested we split it, which always makes me question if they are interested. Old-fashioned I know. Anyway he walked me home, gave me a chaste peck and that was that.

The following week I texted him to see if he wanted to go out again. He replied

“I had a great time on our date but I think we are too different to take this any further”.

I think I was a little too brash and American for him (I told him I thought he was handsome, not a good move apparently). BUT LOOK HOW EASY IT IS. I texted him back saying it was a shame, and that was it. No agonizing, no questioning why they had disappeared. I was bummed, but I didn’t force me to question my entire being.

Location: Oriole

Grade: B+

Date # 2

This is one of the very few times I have successfully used bumble to go on a date (although successful is a strange word).

This guy was a little bro-y in his photos but seemed nice enough. My general mantra is that if we talk and you make the effort to actually ask me out (which is rare) I will go out with you, 100%

Our meeting was a little awkward. Come to find out, he had had lyme disease for two years, has been living at home, can’t have any alcohol (and also doesn’t really look like his photos) and… I was his first date in a long time. It was sort of a lot to reveal in the first ten minutes of a date.

He bought me a glass of wine and a non-alcoholic beer for himself. We sat down and started to chat. In general, it was kind of stunted, I also found out his new job involves him using the software my company sells, which I generally find funny and awkward. He offered to get me another glass of wine, which I accepted. He came back and while we were talking I discovered that he hates cheese boards. Honestly, there is nothing I love more in this entire world. That was a source of contention.

We were still talking when he abruptly got up and said well, let’s call it a night. I laughed and said that I was going to at least finish my glass of wine on my own. I am not one to waste a wine, even if I am not interested. He was so mortified, he clearly had no idea I wasn’t done. I told him not to worry and he could go. He left and then texted me that I was VERY beautiful but that he was sorry, it wouldn’t work. No worries guy, I kind of guessed.

Location: Vagabond

Grade: C+

Date # 3-4

I then decided to mix it up and go out with a New Zealander. We had great chats on hinge and I was really excited to meet up with him.

Our first date was at a wine bar in Covent Garden. It had nice vibes and a decent wine selection. I thought he was super cute (though short-ish, sorry!) and it was pretty easy to chat with him. AGAIN, I consumed a straight bottle of wine with absolutely no food which may have impacted my perception of how well it was going. [[Don’t worry, my tolerance has somewhat improved.]] On the date, he asked when we could next meet up. I was really excited that he wanted to go out again, as you know this is a big accomplishment for me. I then walked over to my good friend’s birthday dinner and drunkenly proceeded to eat french fries off of someone else’s plate and covering them with mayo. Classsss. I still get made fun of for this.

Location: A wine bar

Grade: B

The next time we met up was at a pub, which I don’t usually like, but this one was alright. He also told me a very interesting story about a couple from his work that got outed having an affair because their photo was featured on the pub’s Instagram. Lol. It’s weird to describe this next bit…but I could literally pinpoint the moment he decided he wasn’t interested in me. His tone and body language shifted subtly, and then I knew that was it. I hadn’t made up my mind about him fully, but I knew it was a lost cause. We parted ways and never spoke again.

Location: The Culpeper

Grade: C

More to come soon….

Hello. It’s me.

Well, it certainly has been a while. I actually live in a different country, but guess what… still single! Thankfully, I am in a much better mental space than I was when I last wrote. If you ever read my previous posts, it was clear that I had a heavy touch of le depression clouding the majority of my life. Thanks to modern pharmaceuticals and living in the city I have loved since I was 10, I have a better outlook on life. Dating is still pretty brutal, but the blues I get are a whole lot less dark. So that’s the prologue.

What’s happened since I last wrote…

I lived in London for 3 months in 2018, where I went on several dates when a man that I either loathe or might marry one day, I am still unsure about that one. We still talk. It’s weird.

I also continuously have been involved with a man who I met in 2008. The first time I saw him (at Sanctuary in Boston, RIP) I thought he had the best smile I had ever seen. I knew he was trouble. We saw each other a bunch of times back then and had a weird relationship where we would spend hours on the phone. It started again from 2016 until November 2019. I never wrote about him previously because it’s a saga that has dominated too much of my time already. He is the ultimate Mr. Big of my life; handsome, tall, successful, charming…and the biggest catastrophe and time-suck in my dating history. My friends all are tired of hearing about him, so I will spare you for now. We will come back to him and refer to him as Mr. Big.

After my short-term visa ran out in 2018 I moved back to Boston. I was in a terrible place, I hadn’t wanted to come back and everything seemed bleak and empty. Needless to say, dating did not really go well in this time period. I don’t even remember who I went out with April-September. It was a REAL bad time. There was a lot in my life I wanted to change, and moving to London was the only thing on my radar. Sorry to everyone who had to deal with me in this time period, there was one time I cried 9 days in a row at work. FUN!!!!


Then I met Chris. He is the only man I feel like I can refer to by name because he is really the only man that has never disappointed me. I met him for our first on the day my boss told my work was going to move me back to London, October 5, 2018. It was the greatest day of my life. Chris was the first person I said it out loud to (and no one else was allowed to know for a few months). Chris was (Is) British and at school at HBS (that’s my 5th HBSer if you’re counting). He’s not my normal type, but as I got to know him I was just…head over heels. He is smart without being obnoxious, well-mannered, and the type of man who knows who he is, and is secure with it. And he never hurt me.  I would honestly give him an A- total average across all the times we went out and hung out. He also gave me the best text interaction of my entire dating life.


He even came to my BFFs Christmas party and met all my friends. I saw him the night before I moved to London, and when we were talking he said to me “I was surprised you never asked me where this was going”.  It was the most surprising thing a guy has ever said to me. For once, there was an acknowledgment that this was A THING. He even told me I was a warm and fuzzy person.  I truly think he saw the real me.


The next day, I moved and started a new life…..and continued to text Chris every time I was drunk, which if you have seen my Instagram, is a lot. He humored me but eventually, it dropped off. BUT FEAR not reader,  I saw him again in London in August when he was visiting family. Let me tell you, ALL THE FEELINGS. Do I sometimes think he was probably the one…yeah. But not much I can do about that now.

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But Chris also broke me of my decade-long habit of Mr. Big. When I first visited London a few years ago I would see him each time, he always brought me to beautiful restaurants, gorgeous bars, and his perfect Notting Hill apartment. His life was glamorous and sexy and I felt lucky to be seen by him. One time at a hotel bar, I asked a waitress to take a photo of us and she actually said out loud, wow you guys are a stunning couple. I felt like I was on cloud 9. [[[We will gloss over the time in 2017 we went to dinner and then went to his apartment and he informed me then that he had a gf. That was a bad one, shout out to my friend Kate who came to my London hotel room and basically picked me up off the floor.]]]

Over this painfully-long period, he has always led me on and joked around that we would end up together, sent me cute messages, made time to see me in Boston and London etc, etc etc. The last time we went out was in November 2019, we did a Mayfair Pub Crawl for my birthday. I was sitting with him sipping on a 19-pound cocktail, at Claridge’s and I suddenly said to him,

“We will never be in love. This will never happen, this is not a fairy tale”.


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He laughed it off, but that’s when it hit me. I can be treated well, someone can be nice to me, and not make me feel like shit the day after I see him. At that moment, I wished Chris was there instead. For a decade Mr. Big was on such a pedestal, but just because we had this dramatic and tempestuous saga, doesn’t mean it will ever change. I will never be enough for him, no matter what I will do. And that was our last date. Sometimes I still wonder how he is doing, I texted him recently due to quarantine boredom and he told me he is dating someone. So that’s that.

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Back to London Anna antics in the next post…





You probably assumed I let things go with the guy from my last post? You must not know me very well. I don’t let anything go. I had a feeling that deep down he wasn’t a true ghost-er. While he was away for a month I texted him numerous time. Eventually, he wrote back (I received the text one bottle of wine deep). He said he had been very busy (maybe) and that I had “thrown him out of my apartment and made it clear it was a dealbreaker”.  In my mind, neither of those things were true. We “argued” back and forth for a while and I told him I didn’t feel like I wanted things to have gone this way and that I was sorry etc etc. We texted several times while he was away. When he finally came back I was fairly aggressive in my pursuit of seeing him again. I truly felt it was worth it, and that I owed it to myself to keep trying.

Location: Besito
Outfit: Anxiety, masked by a black peter pan dress and boots
Grade: A-

Two months after our last disastrous date, we went out again. You would think it was awkward and weird. It was not. Despite being so nervous I thought I’d pass out, it was totally normal and adorable. As soon as I saw him walk in, I felt this dumb grin spread across my face. What a muppet. We had so much to talk about, him being in China for a month, me being in Ireland and England for a month.  I was careful to avoid talking about anything that would cause an argument, clearly. The whole time it was just completely natural. He didn’t even blink an eye when I ordered an entire side of queso. I only had two margaritas so I can’t even blame the alcohol.  He drove me home, we talked in the car for a while, he kissed me and left.

I was ecstatic, I kept congratulating myself that I had actually fixed this, brought it back from the dead. I had also been sneaky and mentioned that it was my birthday the following week. I thought to myself, if he cares even remotely, he will remember that.

We texted a little over the next few days, I was careful not to launch back into anything too intensely. Lo and behold, my birthday rolled around and he texted me several times. You should have seen my dumb little face.


The next couple of weeks went slowly downhill. We kept talking, but he would be slower to respond. One time he said he might come by my place because he had ‘time to kill’ (I felt very special), but then changed his mind. The other time he said it wasn’t worth it to drive for an hour in the rain to come see me. Woof. After Thanksgiving I had to just cut the cord, I told him I really liked him, but I couldn’t keep fighting for this he never responded.

[You may think I let it go after this, STILL NO, my friends] I still texted him once in a while and he still responds. The last time I texted him was four days ago. It’s noW February and I live in a different country (more on that later) and I have yet to give this up. What a blithering idiot.

I debated whether I should even write about these next two dudes, but given that I had two dates with them each, it warrants a brief discussion.

Date 1, Gentleman A
Where: Barcelona Wine Bar
Outfit: Jeans and top, going casual because it was Sunday
Grade: B-

I met this guy on Hinge (still the winner in my books). I didn’t know much about him, but he seemed really smart and driven and I usually will accept a date with anyone that actually asks me out, properly.

The date was overall fine, he was very very smart, well-spoken and passionate and I can always appreciate that. He also managed to be even more liberal than I am (which is unusual and a stark contrast to my previous date). Turns out he works in Private equity (I DON’T KNOW HOW I DO THIS EACH TIME). To be honest, I wasn’t super attracted to him -he was very thin and lanky and I have a strong dislike of beards. He correctly assessed that I always prefer alpha males and said that he was acting extra cocky so that I wouldn’t consider him weak and lose interest. Mer, accurate. After the date, he walked me home and went in for the kiss. I thought it was cute. However, when I walked into my apartment he started texting me that I should reconsider, and let him into my place. Uh no. He then said I can cancel this uber any time and come in, you’re so beautiful I can’t resist….Yea no. There are few things less attractive than a man begging like that.

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We kept talking a lot over the next few days and he asked me out again. I was on the fence. However, I reminded myself that every single dating decision I have ever made was incorrect and that I should be open to someone who is clearly smart, successful, and interested.

Date 2; Gentleman A
Where: Ruka
Outfit: Silk wrap top and jeans
Grade B—->D

I was nervous (per usual) for our second date. But once it started, I actually felt much more positive about him. It helped that he showed up in a nice suit and not dressed like a teenager. Ruka is a great date place, its vibe is aggressively sexy. Again, the conversation was good, except I noticed he kept commenting that I wasn’t very peppy and upbeat. Things at work were particularly busy and the following day I was leaving for London for an event. He finally asked me, “do you think you enjoy life to the max, seems like you’re a really serious person”. Mkay. I said that I just had a lot going on. I tried diverting the conversation. But he kept coming back to it. I had the nerve to check my phone (because I was getting several emails from work) and he said to me “I feel like you really struggle with living in the moment”. I had had about an hour of questioning about my personality at this point and was starting to get annoyed. I reminded him that he had collectively known me for about 4 hours. He acknowledged this and we continued talking about other things. After dinner, I was ready to call it a night, but he suggested we go for a walk around the city. I had a feeling I wouldn’t enjoy it, but I was REALLY TRYING to give this a chance. It started off fine until he was asking me, “So what are the things that make you happy, is there anything…do you ever feel happy?”


At this point, I was phenomenally angry. I am so tired of having to justify myself to random men I do not know. I am sure there are plenty of things about his personality that I didn’t immediately like, but I don’t think the solution is a literal interrogation.  I said, listen, I have had a really long day, I am going abroad tomorrow and I have a lot on my mind. You don’t know anything about me, so please stop hammering this point. His response:

It’s just, I think you’re really pretty, and you seem to have a really good and easy life. How could you not be a happier person?

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AGAIN. YOU DO NOT KNOW ME. Women are allowed to be complex beings that have multiple thoughts inside their minds even if some dumb-ass man THINKS THEY ARE PRETTY. At this point, I stopped in the middle of the street and said very precisely and calmly: I have had clinically-diagnosed depression most of my adult life, I am sorry I don’t seem upbeat enough for you. Back the fuck off of me.

He then had this stricken look on this face. He said, a lot of my family has dealt with this, and I said, then you should be more cognizant of the things you say to people who could be dealing with things the best way they can. I turned around and walked away.

THE LAST thing I need is some stranger making me feel like I am not doing enough to hide who I am as a person. I will always be a dark-humored, sarcastic person. And experiences like this remind me that perhaps a life with no human interaction is best.

He obviously texted me immediately after, in case you think I am exaggerating the drama, here is the last thread.


Yeah, I actually did keep trying to date. How funny is that? I will keep this story brief because it’s dumb. Our first date started at a wine bar and ended at Tasty Burger and went exceptionally well, so much so I accidentally invited him to a pub crawl with a bunch of my work friends. That was a COLOSSAL MISTAKE.

The night of the pub crawl, he showed up over an hour later than he said (and with some liquid courage). I was feeling super on edge because I suddenly realized that he was about to meet 10 of my friends. When we went to the first bar, Loco, it was ok. He was doing a good job interacting with people and I was finding it hilarious that I actually came to an event with a date. Then two things happened. 1) I ran into someone that knew C, the guy I wrote about at the beginning of the post and 2) he pulled out an e-cig and I lost my shit. After dealing with the whole Dip incident, I was not ready for another smoker.

I should have my friend AC just fill in here, bc she was present for the entire disaster. I have never had a witness to see things literally go up in flames on a date. I left her alone with him and went to the bathroom to talk myself out of a panic attack. When I came back it was super tense and awkward, I don’t even remember some of the conversation because I was so nervous. Sadly for my friend, she probably remembers it all too well. She headed home and we went on to the next bar on the crawl (mistake). Apparently, he had gone out with one of my coworkers (THANKS, BOSTON), so they uh reconnected and were chatting. Then we were standing around with another coworker of mine, and he said to her “Your freckles are so cute!”, turns to me, and says “Doesn’t she have the cutest freckles?!” …. Uhhh ok, that’s awkward. The rest of the evening was just a mess. We both had way too many drinks, I was deciding that I semi loathed him. When I left the bar, he was still hitting on my coworker.  He texted me after and said he had a great time. He clearly changed his mind overnight. The next morning I said, it was super awkward when you hit on my coworker. his response “I also told your friend AC that she had great dimples, doesn’t mean I was trying to f**k her, I was just trying to brighten her day” followed by “We should agree to go our separate ways”. YES, I THINK SO.

Luckily, a week after this, I relocated to the greatest city on earth, London for a few months. Please be sure to read my next posts in a British accent, because that is how I wrote them.


Left Field Coming In Hot.

So you’re probably wondering how this went downhill so fast with no warning signs, right???

Without getting into the gritty details. After the fifth date, he was driving me home and I had noticed that he had chewing tobacco in his car. I said something annoying off-hand, about how hockey players have disgusting habits. Instead of it being a casual joke. It turned into a massive argument.  Needless to say, it’s a long-term habit that he has, and not a small thing. We argued about it for a long time, mostly because he was pissed I brought it up, and I was annoyed that he had raised his voice and had gotten extremely defensive and mean. I was completely thrown off. The whole time I have been talking to him, he has never yelled at me and been generally low-key and adorable. After some time he apologized and we hung out for another hour or so. Things were calmer and he was back to being his normal self. When he was leaving, he said he had a really good time, apart from our argument, that he would talk to me when he was back. What made everything worse is that he was leaving two days later on a 3 week trip for work. As he was leaving, I had a nasty feeling in the pit of my stomach. I asked him if he was mad at me, and he said no.

The following day I texted him something random we had talked about, he responded but not in his usual style. [I bet you already know where this is going]. The day he was leaving I texted him, no response. I texted him once when he got there about GOT, which we talked about all the time. He wrote back, but only minimally. I texted him two separate times and never heard back. I told myself for days, that he was busy on his work trip abroad, that I was overreacting. But then I looked at this Hinge profile and saw that he had added all new photos from the trip to his profile.


The strangest thing is that for someone who is as psychotic as I am, I found it so easy to be affectionate and warm and fuzzy with him. I suspect that my brain was trying to convince myself that I wasn’t that into him when deep down, I had already made up my mind. I think I will never hear back from him. It sucks for a myriad of reasons.  Chief among them is that I actually miss him. While many of these previous experiences were bouts of infatuation, with men I didn’t even have the chance to get to know,  with C I actually got used to having him there, to talk to, we talked every day for a month. It’s funny because I told so few people about him. I kept thinking that maybe if I didn’t tell everyone, that I didn’t write about it, it would be protected somehow. Ultimately, it doesn’t matter what I think or do or say, it’s never up to me what happens.

After a week, I went back on bumble. One guy sent me a d*ck pick after I asked how his day was going, one guy unmatched me instead of responding. Can’t wait to keep trying this!



Hello.hi. I am back. I have been quite busy casually plowing through the dating apocalypse that is Boston. Here we go.

Random Date 1

Location: Oak Bar
Outfit: Irrelevant
Grade: C

I cant remember any distinguishing details about this man. Other than the fact that he went to really good schools, had recently quit his job, had a shockingly white shirt, and mentioned too many details about his ex gf. Apparently she took the keurig when they broke up. Sad. When he asked me what I wished I had done differently in my twenties (he was 36) I said I wish I had settled for some random semi-decent man. That did not go over well. Apparently he believes in soulmates. Never saw him again. 100% ok with that.

Random Date 2

Location: Bostonia
Outfit: A navy dress and jack rogers (because I correctly assessed he lied about his height)
Grade: B-

He wasn’t really my type, but I found him to be quite interesting and smart. This is creepy of me to observe, but he had the most incredible skin. Literally glowing, not to mention, distractingly perfect teeth. I have never dated a military man, and especially not a former pilot for the navy. Apparently it’s very insulting to call a flight suit a onesie. I thought the date went fairly well. I wasn’t head over heels, but I thought there was enough for a second one.
After our date we texted back and forth for a week. But he didn’t ask me out again. What started to bug me, was that he would text me in the middle of the day all day, and then if I didn’t response, he would say, Busy at work??? And then send a photo of him walking around in Charlestown in the middle of the day. He finished active duty and now is on reserve, which means he only works a few days a month. Meanwhile, I have to go to work…well….every week day. I tried to go with it, but the final straw was when I had said I didn’t work out because I had a long day at work and he wrote back “Sissy”. Cool, bye.

Annnnnnnnnnd then a curious thing happened. I met someone I really liked.We first started talking because his flight was delayed by 7 hours and he was bored out of his mind, and clearly scrolling through his arsenal of Hinge matches. He was straightforward and direct. I was excited when he asked me out.

Date #1
Location: Burro Bar
Outfit: Black mini wrap dress
Grade: A-/B+

When I first saw C, I knew it was him because he looks like literally every other man I have dated. I do love a corn-fed white boy. Apart from the fact that it was 90 degrees, and I sweated through my entire outfit, the date started off shockingly well. It was so easy to get along with him, I was almost giddy. Until… I discovered that we do NOT agree politically. I started full-on panicking immediately. In this current political climate, there are certain non-negotiables for me. I asked him about the two things that I care most about, and his answers were moderate enough that I could calm down. We were able to move past it, because I then discovered that he was living with his parents in NH, after an unfortunate breakup with this live-in gf. There was a lot to talk about. We closed down the restaurant.
After our first date, he immediately tried to make plans again. Looking back, I realize how different this felt from all my other dates. I am an idiot for thinking those other ones would work out in the past, because when it’s easy with someone, it’s SO EASY. There wasn’t ambiguity, or weirdness. Our second date was at Fugakyu. It went really well, at first I was impressed that I had somehow made it to a second date with a human male. But then I realized I was just having a good time with him, and it felt so easy. I even made it 2 hours before my first political dig. That’s a lot of restraint for me. We were the last people at the restaurant. The following day When I asked him if wanted to do something the following Saturday, he said, he would prefer to do something Wednesday, because Saturday was just too far away. I actually smiled at my phone.


Our third date was at Hops and Scotch. Same thing. I found myself being that creepy person that holds hands at a bar table. What?! Again, Same thing. Except this time I even told him I found it really easy to spend time with him. Our fourth date he drove down after a long day of moving. I had been so anxious waiting for him that I accidentally made a VERY STRONG cocktail for myself. By the time he got to my house, I was a little loopy from anticipation. We went to the Fireplace for drinks, where I had one of the strangest drinks of my life. The next morning he was kind enough to take me to the airport at 5:45 AM. If that doesn’t make him boyfriend material, I don’t know what does.Unfortunately that drink came back with a vengeance and he was witness to me throwing up. Very attractive of me. If that doesn’t charm a guy, I just don’t know what does. While I was in London for the week, we texted a little. I found myself actually missing him, wondering how he was. I even bought him a little tourist gift.
I saw him a few days after I got back. He went running and then came to my house to shower. I know it’s so cheesy, but I felt like this was my boyfriend, that was getting ready at my house before going out. We went to dinner at The Abbey. I had become used to going places with him, like we had an easy rhythm. There were things I had to tell him after not seeing him for a week, that I had only talked about with him. It felt great.

Things were going really well. So naturally that night, everything blew up in my face.


I can’t put the update off any longer, I have gotten too many emails, text, comments, and snapchats (Hi Bethel). I never saw John again. I tried to follow all the rules, to not come off as “desperate” as a previous commenter had written. To keep things light and not try to get another date on the books to Just play it cool. He wrote me back a few times, but usually with a one or two day delay and never asking me anything in return. I actually thought we had an (intellectual) connection based on common interests and personality. I have learned is that while maybe I thought something went well, this is never an indication of future success. I just keep trying to understand what wasn’t good enough. Given that we had met previously, he couldn’t have found me too hideous, and given how much we talked prior and during the date, he couldn’t have been too bored. So what was it???

The hardest part is to continually keep trying. Lately, I have found that I am physically incapable of going on a dating app for more than 30 seconds. You can only have people tell you you’re worthless so many times before it becomes second nature. I don’t even blame him for not wanting me,  he’s a smart, cute and successful man. I am sure there are so many options for him to choose from. While I may be enough for a few hours of conversation and drinks, I will never be enough to sustain their interest for the subsequent day or week.

I usually edit out all the “sad” parts of my blog because people tell me it’s too depressing to read. But the truth is that never talking about it makes it much harder to deal with. I am not sad because I haven’t found a boyfriend, I am sad because of the pervasive feeling of aloneness that permeates my thoughts. When you’re in your thirties, things change dramatically. Unlike the inspirational quotes that promise you your friends are the family you choose.  They are not. They have their own growing families and you will always be the outsider. You start to notice that you have nothing in common with the people you used to be closest to. You lead completely different lives. They don’t understand what it’s like to have no one to rely on and feel completely alone and you don’t understand what is like to share your life with someone, through the good and the bad. They worry about where to buy a house so their future children will be in a good school district, you worry about how many years you have left until men stop noticing you at all.

But never fear, I have two potential dates lined up. One just casually mentioned that he is currently homeless and living with his parents and the other, I am not actually sure has a full-time job. Should be good, guys.

Yes, I actually wrote this one.

[I wanted to write this post ASAP before this had a chance to go sour].

Several months ago, I met a cute guy at a bar. YES, in an actual REAL LIFE setting, not on an app. I was at the beehive with some ladies and I saw a cute guy. We had exchanged some words while waiting for drinks and I was hoping he would come talk to me after. He kept looking over at me, so finally I went over to talk to him [#girlpower]. It was so dorky, right as I said something to him, he blurted out “I like your phone case”. Smooth. We ended up talking for probably an hour. He was adorable, self-effacing and charming. It’s not often you meet a man at a bar who wants to discuss Dostoevsky with you while also slipping in a compliment about how beautiful you are. I was totally smitten. He asked for my number as I was leaving and by the time I was in the uber, he asked me to drinks the following week.

I tried not to get excited and assumed that maybe he was just drunk and didn’t mean it. But the following day he confirmed a time and day and location. I was so excited….but the night before he changed his mind and said he wasn’t feeling well. We rescheduled but the following week he stopped responding. I asked him what was going on and he said

Hey, rude of me to ignore you, I am just not ready to date again. Sorry for being a ghost

I had a sneaking suspicion that he had unresolved feelings over an ended relationship when we had first met, so this wasn’t a huge shock. But I was super disappointed. I let it go for a month or so. But then he popped up on a dating app, so I sent him a cute text.  We started talking again and made plans to do something. I was cautiously optimistic, but he canceled last minute because of a family thing. I think most women would give up at this point. But I kept telling myself, this was something different. That I owed to myself to pursue it.   I (1) rarely meet people in real life (2) rarely meet someone I am really interested in.

About a month later I reached out again. He sent me a hilariously organized whiteboard that showed he was traveling all weekends for the rest of the summer. But I suggested a Thursday drinks date. To my surprise, he agreed, and then….it actually happened. All I can tell you is that I was 100% right.

Location: Tiger Mama

Outfit: Red off the shoulder bodysuit, dark jeans and wedges

Grade: Hard A

As soon as I walked in (I was disastrously 16 min late) and saw his little face I felt really excited. As you all know, I deeply dread all online dating and have an immense sense of anxiety each time I have to meet a TOTAL STRANGER AT A BAR.  Not so here, we have already met, so that horrendous awkward fumbling did not occur.  It was easy and flirty right off the bat.

There were so many things for us to talk about. He is in a book club like I am, he works in a similar field to me, he likes to travel. I dont even remember having a moment of awkward silence. Our biggest source of contention is that he likes Halo Top and I think it tastes like crystalized chemicals. I did not need to talk about online dating or failed relationships, or say weird things about myself, or mention how much I hate Boston because, in this moment, I didn’t feel any of these things. I just felt like a girl on a date with a cute, dorky guy. What started out as a drink turned into several drinks and a full dinner. I knew I liked him when I was genuinely middle-school school excited because his leg was touching mine under the table. ehehehheh.

I have gotten so tired of playing the game and pretending to be cool on dates when I actually like someone so I finally said,

I dont know if this is a controversial statement, but I am really glad that I agreessively made this happen because I am really happy to be here.

and he said,  Me too.

At the end of the night, he wasn’t sure if he wanted another drink, so we ended up splitting our drink. How cute is that? Heart Eye Emoji all over the place.

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I don’t know that this will go any differently that my other failed attempts. I don’t know that this will not end up being the next JD failure. I may never see him again. But I know that those 4ish hours were the first in a while when I felt light and optimistic.  I had been right, that I had judged our interaction correctly, that there was something there, that I can be open and outgoing and nice and that sometimes you have to fight for something you want.

Rules, be damned, I sent him a text after that said “I had a really good time tonight” and he wrote back “me too, thanks for putting up with me for so long”


A tale of 3 dates

It’s like, pretty hilarious that I keep trying to do this.

Post cowboy shittiness, I waited a little while then forced myself to get back into things. Over time, I have become less and less picky. Last week I ended up talking to 5 guys online, and actually was asked out by  3.

Date #1


I started talking to D on bumble. He had recently moved back to Boston after living all over the country. Originally he is from the midwest, so I had high hopes he would be a little nicer than what I’m used to dealing with. He was sweet and straightforward, the conversation was pretty easy and I was excited to meet him.

Location: Highball, Serafina
Outfit: Polka dot wrap dress with jack rogers (because I correctly assessed he’d be too short for me to wear heels)
Grade: B

When he showed up to Highball I thought he was very cute, much smaller than most of the guys I date, but dressed nicely.  The conversation was a little more stunted in person. We don’t have much in common and I definitely wasn’t feeling the usual conversational spark. I tried to remind myself that banter is not always instantaneous and that I needed to give him a chance and remember that he might be shy. Once I felt a little more relaxed about it, I started to warm up to him.  I thought it might be fun to stop by Serafina (My team goes there every single Friday). I am usually a lot more normal when my friends are around, and I thought maybe going there would make it less of a THIS IS A FIRST DATE atmosphere.

I was right, going there definitely made me more open and relaxed and he seemed to be having a great time. He met a few of my coworkers and everything was going well. He apologized but said he had to go meet his friend to watch the Celtics game. I walked him out and gave him a hug and proceeded to have several more cocktails. I sent him a Thank you text and got this as a response. FullSizeRender (2)

I thought I was in the clear, that he was interested and that we would go out again. I annoyingly pestered all my friends about it, and they said he seemed cute and nice. WOO.  I sent a follow-up text on Monday asking how the weekend had been….no answer. I texted again, he responded and apologized for missing the previous text and that things were pretty crazy at work etc etc etc. I texted him once again and never heard back. Cool.

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Date #2.

Like I said, I have been far less picky about who I talk to online. I started talking to a guy on Happn (aka my least favorite app). He was slightly odd in some of his phrasing and an aggressive user of emojis. I ignored that and talked to him anyway.  He asked me out and I figured, why not. Clearly, I need the practice.

Location: Fairstead Kitchen
Outfit: Irrelevant, didn’t even remove my coat
Grade: C

When I walked in, he was deep in conversation with the waitress and I almost felt rude interrupting. I immediately knew I wasn’t attracted to him. I typically don’t go for men who are wearing more jewelry than I am.  He was a little bit awkward and I tried to be friendly while we were talking. The good news was that I wasn’t nervous at all, I just wanted to be polite and not make it too long of an evening. I was also DYING from allergies and kept having to excuse myself to take hits of Flonase and allergy drops.

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We talked about a bunch of stuff, we had some things in common. He kept using these strange expressions like “Well, that’s a DAMN shame” as if he was some Cary Grant type fellow. I also only had one glass of champagne, while he powered through 3 vdateodka drinks. I apologized and said I had to call it a night. I almost felt empowered because I remembered that sometimes I am also allowed to not like someone, and thats it’s not always just about trying to seem attractive to a guy. He sent a few texts after, to which I politely responded but made no effort.


Date #3.

I met date 3 on Bumble. He is a new transplant to Boston (that’s my new target audience) from the midwest. Again, high hopes for a nice personality. We had a lot of chatting before he actually asked me out, and I was excited to meet him.

Location: Yvonne’s [you can tell he is new, and I picked the date spot]
Outfit: Blue silk top, dark jeans and boots (bonus – this one was tall enough that I can wear heels)
Grade: A-

When I walked in, he was already sitting down. I immediately thought he was very cute, great smile and a sharp dresser. I didn’t even have a chance to get very nervous because he is very open and outgoing.  The conversation flowed extremely easily, with him making jokes about East Coast girls and me commenting on his goofy and adorable Minnesota accent. Because we both work in a SaaS tech company, we had plenty to talk about work-wise as well (which I find to be helpful on first dates), he also likes to travel and watches the same shows etc etc. I knew I liked him immediately. Apart from one disagreement on uh…. certain partying choices, everything seemed great. We spent most of the date laughing.  He even told me that for my birthday, he was going to go back home and get me a baby otter, one of my most favorite animals.

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Our date was from 6:30 to 10. He walked me to the T and kissed me twice and said he had a great time. I said the same and thanked him for my drinks. I texted my friend immediately and said I was obsessed and liked him so much.  I texted him the following day and we went back and forth a little. Since it was a long weekend, I mentioned to him that I would be around and that we should do something. He replied that he would be too, and we should. I felt pumped. Fast forward 2 days, he decided to go to a concert and didn’t make any suggestions for a time for a second date. I asked him how the concert had been and never heard back. Amazing.


Pray tell: how do I not lose my mind here? How does this not carry me into a deep depression? How do I continuously put myself out there, knowing that even when I think something good could happen, I am constantly proven wrong? It makes me feel that I am not good enough for anyone, not good enough to sustain human interest for more than 48 consecutive hours. Are they lying when they say they had a good time? Are the other girls on these apps so much better than me? It’s funny because I thought last year was as tough as it could get, I was wrong. I feel like I no longer have anything in common with any of my friends, that there is no one I can really talk to. People just don’t get how hard this really is. Without getting into the dark details, you can only withstand so many forms of rejection before you really lose it. Am I, in fact, a deep-sea monster, so horrifying that it cannot be seen in the light of day?

An update.

Hi, fine readers,  I am back. Happy to share that I have been in a great relationship for about a year and I am super happy……JUST KIDDING, YOU GUYS. Things are somehow even worse than when I last wrote.

The founding member of the Trio, who I referenced in my last post, got engaged. In a shocking turn of events, she is younger than me, prettier than me, and dated him less time than I knew him [also an actual socialite]. If not for my wonderful, soothing friend who happened to be staying with me the night I accidentally made the discovery, I would still probably be in bed, months later. It was one of the single worst seconds of my life.  I have been bracing myself for this for a while. All this time, I hoped I would be involved with someone else when this happened. This is the man who told me he’d never get married because he wouldn’t find a girl that was worth it, apparently he did. Added bonus, I am at a wedding the day he gets married.

Since my last post in February, I tried trudging along through the dating apps, but months went by without anyone asking me out. I was then briefly involved with the single most handsome man I’ve ever been with. He’s my standard type, HBS-bound, Investment Banker, 6’3 etc.

From the moment I met him, I knew he would be trouble. I am cold, but he is ICE. No matter how clear he was that we would never date, it still felt better than what I had been trying to do before.  Being with him made me feel wanted, even for a brief moment. Like I wasn’t a reptile from the bottom of the ocean. Every time he was a jerk, I wanted to be snappy with him, but then I’d look at that face and I would LITERALLY forget what I was planning on saying


He dumped me by saying  “I’m moving on” when I asked him if he wanted to hang out again. I was mostly just sad I wouldn’t see that beautiful face again.

About a month later, I went on a date with another guy, also an HBS student (I have the market cornered) who is on the same rugby team as the British guy from “Live a little”. I wasn’t particularly attracted to him, but I liked how ambitious and smart he was, and let’s be honest, I am in no place to turn down dates. Our first date was a little awkward. He is a pretty intense person, and it made me very anxious, which in turn contributed to me drinking 4 vodka sodas without dinner. He would rapid fire ask me questions…and I would try to answer them and then he would get annoyed I wasn’t asking him any questions. He asked me how I felt about online dating and tinder and I was my typical sarcastic self. I may have also mentioned that I am “dead inside” and that I have a wall up because I have been hurt before. I thought maybe if I said these things he would understand that in generally, I’m not an effusive person.  The date itself felt very stunted and awkward. I usually don’t have such a hard time making conversation, so I assumed I had just been off and accepted the invite for another date. I dont know if its because he isnt working, and is in school but he would text me constantly and then play pretend that he was crushed by how slow I was to respond.

On our second date, I was so anxious I started to feel nauseous almost 3 hours before the date. I already knew I didn’t like him, but I felt like he deserved another shot, and that I was being overly critical (weird). We went out to dinner and I legitimately consumed one tortilla chip. And if you know me, you know I eat like a wildling. He kept saying my answers were evasive and that he couldn’t get a good sense of who I am. He kept asking me “what are the things that make you happy, and you can’t say cheese again“. “Do you feel like you will ever be able to be in love, and open up to someone?” You cant corner a person with clinical depression and harass them into talking about these things. He was almost pushing me into a panic attack.  As you know, my least favorite comment that a man can make is “I just find you very difficult to read“. When I finally said “I don’t really like when people push me to answer questions like this” he said “Well, any man who doesn’t ask you this is just trying to f*&ck you”. Cool. I never texted him again

“Well, any man who doesn’t ask you this, is just trying to f*&ck you”.

Cool. I never texted him again

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I then went out with a new bumble guy. He was very sweet in our text conversation and I was happy when he immediately asked me out. When he walked in, my heart skipped a beat. He was smiley and goofy and adorable. The whole date went great, I could tell I was being so well-behaved, like night and day from those other two dates. I didn’t even make any of my trademark sarcastic jokes. He had to go to a basketball game so after he had a drink he had to head out. I texted him and said “Thanks for the drink, I had a great time” He wrote back “Anytime, we’ll have to do it again soon”. I called my friend and blabbered on like an idiot the entire cab ride. That I had been wrong to go out with all these investment banker douchebags, that I don’t even want to marry someone who has a lot of money, that I don’t care, because once you meet someone who is so sweet, the rest of it doesn’t matter.

The following day I texted him. He didn’t reply for a while and I started feeling nervous. I thought NOPE, this isn’t going to happen with this guy, you had a great time. He eventually wrote back. This continued for a few days until he never responded. It immediately threw me into a pit of darkness. As I call it, THE HOLE. He then texted me a few days later apologizing profusely for being a jerk and that he had been on a boys weekend with his friends in Maine. I felt back on track and asked if he wanted to something that week. I never heard back.

The following weekend, emboldened by my favorite drink at Yvonnes, I texted him again “So was that a hard no on hanging out?” he immediately wrote back and said

“Hey! I am sorry! Had a pretty long week. Didn’t mean to be an asshole. I had a really great time and you are sweet but im just not really in the right place to date”  

I was so stunned Immediately wrote back “Woah. No one has ever called me sweet before” [true] and he said “Well I had a good time and you are sweet, just have a lot going on right now“. That was it.

I felt like the world’s biggest idiot. I knew I had been good on that date, that he had seen a glimpse of what I am really like, that I had been warm and genuine. But that it is still never enough. [He is still on bumble btw].


Here’s a quick breakdown of the dates that followed in the past few months. They don’t even need codenames or long descriptions.

1. Lawyer guy.

Where: Highball
Grade: B
Status: Ghosted. Not sure why

2. Columbian guy.

Where: Barcelona Wine Bar
Grade: B+

I enjoyed this date, he was confident, well-traveled and smart, and a sexy Spanish accent never hurt anyone. I thought this one actually went well. He dropped me off in the car and kissed me. When he tried to make out with me and I demurred, he said “What… I thought Russians were supposed to be the sexy ones”

Status: Ghosted. Because I am not sexy.

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3. Standard finance guy

Where: 6B
Grade: C+
Status: Whatever

This guy talked to me more before our dates than anyone I have ever met. We texted all day every single day leading up to our meeting. When we actually met, I was not attracted to him and noticed a lot of huge emotional red flags. I tried to tell myself that he deserved another chance. I never heard back from him again.

4. Cowboy

Location: Nebo
Grade: A-

I matched with a new guy last month. He was definitely different from my usual type and as an awkward bonus, he works in my building. He was pretty funny in our conversations, and despite having a deep-seated fear of smooth sales guys (founding member of the trio) I thought I’d give it a shot.

He took me to a spot I really like, which made me feel less nervous. We hit it off immediately. He was very sarcastic for a Kentucky-raised, horse-riding cowboy. He gently poked fun at a lot of the things I said, which made me laugh. I always believe that great banter is crucial on a date. He also peppered in some sweet comments, that I had beautiful eyes, that he was really enjoying our date, that he couldn’t wait to show me how amazing an F150 truck really was. I mentioned to him that I find it hard to trust people when I meet them initially because I have been hurt in the past, his response was that I just needed a southern gentleman to make me have faith again.  I don’t know if it was the 5 drinks, but I felt a lot of excitement.  By 11, we were the last people in the restaurant and they were desperate for us to leave. He walked me to the uber, kissed me and left.

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I felt very excited about this guy. We texted back and forth that week. I knew he was away for the weekend so I said we should do something when he was back. There was a slight lag (where I tried not to panic), then he said we definitely should get together when he was back. That weekend he sent me a “I can’t wait to makeout” text, which I thought was adorable. The following week we went back and forth where I tried to plan our second date. One example response was “I can’t tonight, I have a team Sox game outing, otherwise, I’d totally be down!!” etc etc. Just enough to make me think I was still in the running. I tried several more times the following week, then I sent him “I really wanted to go out again, but you are making this pretty hard.” No answer.  Cool.

The good news: I am so afraid to run into him, that I have stopped leaving my desk at work and my Starbucks spending has really gone down.