This is a necessarily long entry, so please bear with me.

I started talking to a software engineer at Facebook on Bumble last week. It was around Thanksgiving, so obviously we discussed pie and how much we love it. Then he asked if it would be too “exotic” to bake a pie together as our first date. I thought it could either be a great idea or a terrible idea, and after talking it through some more, we decided to make a pie at his place last night. Just the two of us and his puppy (read: stranger danger). He bought the ingredients, I brought over my pie gear, and we got to work.

As we ate Seamless and waited for the crust to bake, it somehow came up that we would share what we thought were aspects of ourselves that could be dealbreakers for other people. He went first.

  1. He’s an alcoholic and is 4 months sober. (Keep in mind that he’s about a month younger than me.)
  2. He’s heavily medicated for depression. (Used to be worse, but now that they’ve got his drugs figured out, he feels great.)

Ok, sure. Pretty big bombs, but there are worse things in life. I, of course, am racking my brain trying to “compete” with these, and can’t come up with anything much better than “I make my own deodorant” and “I believe in horoscopes, tarot cards, palm reading, etc.”

The timer goes off to take the pie crust out of the oven. He asks if I’m going to do it and I say no, we’re both able-bodied citizens and that he can do it. He says no he’s not. I ask what he means and he tells me he had a stroke while in the womb. (Bomb #3) They discovered it after he was born and his left side just didn’t develop as well as the right. I never would have noticed this had he not told me, and still couldn’t really tell either way—so again, not necessarily a dealbreaker.

As we’re waiting for the pie to bake, we’re sitting on the couch and talking about all the random things in life. One of our topics ends up being micropenises, where I go off talking about how bad I feel for people with micropenises because they don’t make condoms that small. He asks if I feel the same way about people on the other end of the spectrum. I say it’s different because even though they also have a hard time with sex, it’s not an emasculation thing. But I digress.

As I’ve been at his apartment for about 3 hours, I’ve noticed that he has an ashtray with cigarette butts. At one point he says he’s going to go out for a cigarette and then asks if I’m “normal and hate cigarettes,” and I say yes. So he vapes instead. Being a smoker is basically a dealbreaker for me, but I gave Bartender a chance, so why not give Pie Boy one as well.

The pie is done and now we’re waiting for it to cool before eating. I should also mention that throughout the night, there was never any flirtation or spark or real chemistry. Just two people making a pie. But then he starts asking some sex-themed questions. But let’s also remember that he’s an engineer (which means he’s an awkward nerd, and of course I, too, am awkward) and these didn’t come off as flirty or aggressive or anything except curious, so I engage. He asks if I have any weird sex stuff. I say no, I’m pretty boring. I ask him the same. He says he’s also pretty vanilla, but, well, yea he guesses there are some things that could make sex with him difficult.

  • My first thought: Is it the stroke? Can he not really move the left side of his body, and the girl has to do all the work?
  • My second thought: He wouldn’t have joked about having a micropenis if he actually had one, right?

I was wrong on both. As it turns out, he’s too large for Magnum XL condoms! He recently discovered larger ones and is waiting for them to arrive in the mail, but yes this has caused difficulty with women in the past. I resisted the urge to ask how many times he did manage to squeeze it in, so I don’t know that much about it and certainly did not see it. He even worries that his dick is sometimes visible through his pants, but no one has ever pointed it out to him, so he’s not sure. I couldn’t tell you either way because it was midnight and he was sitting and I was tired and didn’t want to stare (I wasn’t gonna make him stand up and pose for me). But I tell you, of the many surprising things I learned about him during this very open, honest, and informative date, THIS is what I consider to be my dealbreaker, or rather: vaginabreaker.

We kept talking, ate some pie, and I eventually packed my things and left at 12:45am to complete this 5-hour date. We shared an awkward half hug when I left, and some very brief texts today about pie (I initiated).

Closing Thoughts:

  • It was a positive, fun date overall and I don’t regret a thing.
  • It was great to have an activity to do, vs just staring at each other while chugging beers.
  • We covered 4 dates worth of material in just one, and man do I love efficiency.
  • He’s very smart and funny (and pretty cute), and I’d be interested in hanging out again, but certainly only if things were to be kept above the belt.
  • One of my dealbreaker traits we discussed was that I’m not very affectionate and have a hard time expressing my feelings. So, I’m pondering reaching out in some capacity if I don’t hear from him in a few days to perhaps express the gist of the previous thought.
  • Did anyone notice the foreshadowing at the very beginning of this email? :D


If you didn’t hear already, Bartender obviously ghosted. #storyofmylife But also, whatever—he moves in like 2 weeks, and his cigarette smoke burned my eyes.

Since then, I’ve been on two dates with a Bumble boy who works for an elevator company. Elevator Boy is cute and fun to hang out with, but I don’t feel more-than-friends chemistry, so I don’t think I should let a third date happen.

Hinge, Bumble, and The League all mysteriously ended up on my phone again… Weird, right?? (Actually, I should really delete The League. It’s simply the worst.)

P.S. For those of you who’ve been on this list since the beginning, I hope I’ve made the last year of your life all the more entertaining with my charming tales of my not-so-charming dalliances. #happybelatedanniversary #besos


Last night, Bartender and I had plans to go play shuffleboard, but at the last minute realized it’s closed on Mondays. After much back and forth and indecision, he suggested Netflix and couch. I hesitantly accepted, after first establishing that nothing would happen. I arrived, we got snacks, and he actually respected my boundaries a little too well, sitting a full cushion away from me. Towards the end, I scootched over for some G-rated physical contact. Before I left, he asked if “nothing would happen” meant we couldn’t make out. I said no, and so we did. Then he walked me to the subway station (and actually swiped in to escort me down to the platform).

Deep thoughts:

  • He established early on that he is not a texter, and he’s sticking to it. This does not bother me and I appreciate being forewarned. I think it also helps keep Psycho Girl Emily at bay.
  • The fact that he leaves soon removes a ton of pressure and anxiety on my end (and potentially his?) about how much I like him and what this could be and how we should interact. I know it should always be like that, but… yea right.
  • His apartment is “boy” to the nth degree, and he has a twin bed, so I think it’s safe to say future plans will take place at my solo bachelorette pad.

#34 Have I got a story for you!

Thursday night, my friend and I wound up at The Standard Biergarten. We were ordering drinks and admiring how cute the bartender was. As she was signing her receipt, I had her write “white girl thinks you’re hot” with my number. Gave it back, drank our drinks, went home and ate some wings.

Friday morning, I wake up to a text from a random number (with a photo of the receipt) saying, “oh hey there.” I respond, and he……. doesn’t respond. TYPICAL. So later that evening while drinking at work, I decide to double text and ask, “do you even know which white girl I am?” He actually does and the conversation continues as we decide to meet up later that night.

We met up at 10 and had a couple drinks at a bar near me. Then, he asked if I wanted to go to another bar, and I did but told him I wouldn’t get another drink because I had to wake up early. We go to the next bar and I desperately rush to the bathroom. I come out and he’s ordered himself a beer and a club soda for me, which I was not expecting and thought was very nice. We kissed in the bar, and then he walked me home, and we kissed some more outside. He tried to come in but I shut him down. We have tentative plans to do something on Monday.

Things to note:

  • He’s an Air Force baby so he was born in Germany and lived there for some time and speaks German. #hot
  • He smokes. #nothot
  • In 7 weeks, he is moving to Berlin for a 2-year masters program. #iamamagnetformenthatmove
  • I asked him how often girls give him their numbers via receipt, and how often he follows up. He said he’s gotten around 30 numbers (I didn’t ask how long he’s been bartending, so not sure what his ratio is), but that I’m the first he’s responded to. Apparently the other numbers had been from uggos or while he was already seeing someone.  #ifeelcoolandspecial

So, whatever happens, this is a lesson to all to give your phone number to strangers! #otl #irl