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.

Farewell Musings

After Dates #23, 24 and the never-written #25 I was feeling great about T. I secretly thought to myself, This is it. This is how people just start dating someone. We talked every single day since we met, and he was so nice to me. I felt very optimistic and hopeful. We made plans for him to come to my friend’s holiday party and I was so excited. He could meet all my friends and I would finally have a date at a party. Except he never made it. He allegedly got in a car accident on the way there (I had specifically asked him not to drive). When he texted me, my immediate response was “I told you not to drive, are you ok” He said he was fine and I wanted him to still come to the party but he had to take the car home etc. He didn’t even respond to my last text. I then decided to text the Brit even though we hadn’t texted in 2 weeks. He wrote back “Who is this?” Ouch. I had to reach out to T the next day and ask if everything was ok. He said he was fine again and hanging out with friends.

The following week I tried to make plans with him a few times. Finally his response was “I am busy till February” (It was 12/23) I finally bit the bullet and said “It seems like you’ve really pulled back here” he said

“You’re right, I’m sorry. things have been very hectic and I am not giving you the attention you want. Ill get in touch after the holidays”


Just what you want before the holidays. I tried my best and didn’t talk to him for a 4 days. I sent him a cute photo from an inside joke and he wrote back and we chatted a little. The night before New Years (my least favorite holiday of the year) I talked to him again and asked if he wanted to do something Friday, he was busy. Then I said Maybe Saturday, not sure if I should keep trying here. He said “Listen. I told you I was busy” And that was it for me. He made me feel so shitty and unwanted that I went and deleted every trace of him from my phone and haven’t heard anything since.

I don’t really know what happened. My friend said it was probably my response after the accident that annoyed him. Other people said maybe he was just busy. Most people just said he was a jerk. I suspect he probably met someone better. The irony of course, is that he told me he thought I was guarded and that it would take a long time for me to let someone in.


I started writing this blog because I wanted a place to share both the funny and frustrating dating experiences I was going through during my 30th year. So many of my friends and even strangers read it and gave me encouragement and feedback and I loved hearing from everyone. But each time things ended badly I felt so embarrassed and ashamed to come back and admit I had failed yet again It was like constantly re-living how painful it was to get dumped/rejected. I tried messaging five of my matches this week and not a single one wrote back. I feel genuinely exhausted.

I never wrote about him, but my first (likely only) love once said something to me (after being involved a year) that never left my mind. I told him I wanted to be his girlfriend and he thought about it and said

No man, when I settle down with an actual girlfriend she will be so special. When she walks into a room everyone will stop and look at her.

I’ve always been pursuing this imaginary notion that I will one day be the most special to someone. But back then he also planted the seed in my mind that it’s impossible, and it’s something I never got over.

I thought maybe going on 29 dates would teach me something. And I did make it to 29 (I never posted about a 3rd date with JD, or my last date with Canada, or the Inbound date etc). All I have learned is that it’s so much harder than I thought, that there are no guarantees in life that everyone finds love, or even like. That maybe having a career, and a healthy family and friends is all that I can ask for. When I talk to my married friends they say things like “You shouldn’t need a man to be happy”,”Things happen for a reason”,”Everything will work out”, “your life can’t revolve around finding a man” but when I talk to my few single friends they say “It’s happened to me a million times”,”I’ve given up”,”There’s no one left”, “Why keep trying”. I don’t know what will come next. But I have decided to take a step back and stop putting myself out there so much. So for now, no more blogging.


Thank you all for taking the time to read all my insane ramblings.

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xo, Anna

24: Just like I planned

I was feeling pretty good about things after our first date (Tuesday) and lo and behold the next night (while he was at a holiday party) I got several very cute texts asking when he could take me out again. We made tentative plans for Saturday and I went about the rest of my day. Then Thursday morning he asked me what I was doing. Luckily I had plans with my coworkers to go out, so my outfit and hair situation was above average. I told him that we should meet up later while I was out with my team. I didn’t really expect him to follow through, but he did and said he would stop by around 7 at Carrie Nation (Yes, where I went with Canada, Yes where I went with JD, and another first date).

I was at the bar with my team when I suddenly started to get VERY NERVOUS. I don’t really know why, but I started totally panicking about why I was having him come meet me, would he like my friends and more importantly, would my friends like him? And was this a good idea if we had only been on one date. My solution was to start consuming a large amount of Prosecco. Bubbles will help~! I had already had 3 glasses and two bites of cheese when he got there. The rest of the night was a bit of a blur because I added two more glasses of champagne and no more food substance. I was so hyped up and nervous I barely remember what I was saying. All I kept thinking in my head was, HOW WEIRD IS THIS. There’s a man here who likes me. My friends decided to head home (after apparently debating whether it was safe to leave me LULZ). My guy’s friend drove us to his car and he offered to drive me home. This is where it starts to go downhill.


We drove up to my house and I was about to get out of the car when I realized…I didn’t have my keys.  I live alone and happened to borrow the spare set of keys to give to a visiting friend, the second set of spare keys were with my parents, who were in Amsterdam. I immediately started freaking out. He said it was fine and that we would find them. He then drove me all the way back to the bar. I was semi hysterical by this point. I am not a person who is EVER careless, or sloppy or loses things. I was rooting around the bar like an insane person before he pulled me out of there and drove back to his house. I was going down all the possible scenarios, that I drunkenly lost them, that someone stole them, that I would get robbed, that I was going to have to replace the locks in my entire building. He told me to relax, that they were probably at work and that I was winding myself up . I told him he was insane, and that this was the worst thing that had ever happened to me. I texted probably ten people with an assortment of “HELP me” “Are you awake” “I have an emergency”. Oddly enough my friends were’t awake at 2 AM on a Thursday [you should have seen the responses Friday morning]. I am the most Type-A individual ever. Being in strange place without my things, or a cute outfit or even makeup remover is my ultimate nightmare.

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He clearly has experience dealing with batshit crazy women, because he stayed fairly calm the entire time. The next morning I woke up (well I never actually slept)  I got the best text of my life, that my keys were quietly sitting on my desk at work. I had to apologize multiple times, 1) for telling him there was no way the keys were at work 2) for telling him this was the worst night of my life and for an assortment of other GREMLIN-like comments. I told him the good news was that he has already seen what I look like in the midst of a panic attack.


The biggest surprise was that he actually talked to me again, and we hung out Saturday night as well. Three dates in 5 days. I don’t know guys. My brain cannot compute. I remain a wildly confusing human being so it’s really a question of how long he can stick it out.

Lesson Learned: Be a sane individual 

23: Low Expectations

After my horrendous date #22, I was feeling a bit un-enthused about the prospect of meeting anymore men. I had been talking to a guy on Tinder for about a week. His photos were pretty MEH (including the famed bathroom selfie) but the conversation was pretty good. He asked me to have drinks and I agreed, thinking at least it will be another date towards 29.

As I was walking to the bar. I started giving myself a pep talk.  1) Make sure you hug him when you approach. 2) Make sure you smile even if you want to stab yourself in the face.  3) Don’t be too sarcastic. Just don’t be yourself in general.

When I walked into the bar I saw a really tall, cute man and thought well, that’s definitely not him. AND IT WAS. This has never happened in the history of my dating. Giving him a hug was pretty easy.

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We got a drink at the very crowded bar. Because I thought he was going to be short I wore very low heels. I got elbowed twice by some aggressive humans and he switched places with me, I thought that was cute. He is pretty outgoing, so the conversation was very easy. Because we had chatted a bit before meeting we didn’t have to have a lot of the awkward into conversations. He had already put his name for a table (good planning!) so we moved to sit down. After a quick run through of all the things I cannot eat, we settled on some tapas. We had pretty good banter, and he is a bit of a smart-ass. Not as much as me though, because that’s not scientifically possible.

I have to say that the highlight of my night was this amazing elderly couple that came in and sat at the table next to us. She was the most fabulous human and was wearing rose-colored glasses and they had matching outfits. I creepily observed them from a far and we decided to make up a story about their lives. He tried to get me to go talk to them but I was too shy (Dstappy probably would have).

When he walked me to his car he stopped and opened the car door for me. WHAT. I think that’s the second time that’s ever happened to me. He dropped me off at home and I waltzed into my apartment feeling like Beyonce.

I had such intense anxiety leading up to this date. I kept thinking that maybe this is all my fault, and that I am horrible and cold when I first meet people. But after this date I realized when I feel comfortable I can be outgoing and friendly and smile. And I don’t need to value the opinions of some idiot who will never get to know me.

Lesson Learned: I am not the worst.


ps. He had a holiday party the next night and texted me that he wants to see me again soon and that he had a really good time. This was me when I got the text