I kissed a Trump supporter and it was as terrible as it sounds.

(^^^good memoir title, no?)

Long story short, I went out with a Manhattan douchebag from Beverly Hills on Saturday who’s never been to Brooklyn and who flaked on me the first time when we were in LA. All the warning signs were there, but I went out of curiosity to discover if his grandpa was in fact married to a recent Miss Universe winner (his seemingly serious response to a joke of mine). Nope, the trollop in the red dress on his profile was just his ex (one of many red flags). He was an entertaining person to witness, but I should have left as soon as politics came up so that I could have avoided what came next. The kiss wasn’t exactly consensual and I aborted (zing!) as fast as possible. At least he didn’t grab my pussy, right? But I know he was thinking about it because he invited me back to his apartment! I practically scoffed in denial but I think he found my snarkiness cute and sarcastic, when in fact I’d never been so sincere. No date has ever left such a bad taste in my mouth. EW EW EW EW EW!!!!!!

On Sunday, I cleansed myself of every woman’s nightmare by getting brunch with a cute, tall, high quality human from Astoria. I was even my true hippie self on this date, using my own cloth napkin at the restaurant because they only offered paper. He didn’t run away screaming, and we talked about how I felt guilty drinking from the plastic cup. I even told him about my appalling Saturday night—thankfully, he was appalled as well. We ate, went to a bar for beer, and it was all very enjoyable; though I can’t shake the feeling that I was at my most awkward. I told him I’d like to see him again, and he politely agreed, but we’ll see what happens.

After Pie Boy and my cloth napkin date, I realized I’ve probably been pretty superficial on most dates, not letting any of these men get to know who I actually am. So, in this new year, I’m going to try to be better about being as honest and forthcoming as possible, not caring if it makes me seem undesirable. Watch out, boys!

P.S. Trump Supporter didn’t drink on our date because he was finishing up antibiotics for a sinus infection. I know how antibiotics work and he shouldn’t have been contagious at that point, and yet I feel a cold coming on. Did he infect me with his misogyny?? Are Trump supporters actually as diseased as we think they are?? BLECH!


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