Encounter #16.1: In and Out Date

App: Tinder

Name: Trey*

Date Location: District Tap House

Location Review: N/A – Could not make an effective review

Date Duration: 7 minutes (a new record)

What Happened:

Trey and I had been chatting and texting for nearly 4 days before he asked me out. He seemed pretty normal. Aside from looking like a hedgehog, he worked in finance, was athletic, grew up in Westchester, lived in Hell’s Kitchen, liked to drink, and loved dogs. Nothing too noteworthy.

Just to preface the following events, below was the text exchange that day and a few days prior:

Screenshot batch 3 (1).jpg

Got it? Remember that? Cool.

I met him at the bar and said it was super busy inside but he knew of a spot a few blocks down. We walked over and did small talk about work. Nothing special. We got to the second bar which was also full. I let him know that I was fine with staying there and standing but if he wanted to change locations, that was also fine. Trey said he wasn’t feeling it so we walked out.

When he said he wasn’t feeling it, he meant about the whole situation. We were standing outside and he said, “Yeahh, I’m not feeling this. I’m tired. I’m just going to go home. Nice meeting you”. AND WALKED AWAY.

Okay, I recognize that I am not a supermodel by any means. Probably a 7 with a personality that could bump me to an 8 depending on the crowd. That being said, I do make a point to have photos on my profile that look like me. Too many times have I gone to meet a guy expecting Hottie McHotpants and instead got Homer Simpson. WTF was this asshole expecting? If he didn’t want to go out why didn’t he just cancel when I texted him that day? WHO RAISED HIM?

As I walked to the train I unmatched him and blocked his number. I don’t care what his excuse was going to be. If you’re going to pull that shit I don’t need you in my life.



Encounter #12.2: A Hanukah Miracle

App: Bumble

Name: Pete*

Date Location: Amsterdam Billiards followed by Fat Cat Lounge

Location Review: 3.0 Stars – Amsterdam Billiards: Definitely divey which isn’t a bad thing but you need to look out if it’s a league night if you want a pool table.

4.0 Stars – Fat Cat Lounge: Super cool bar. There’s live jazz/swing music, cheap drinks, and dark lighting

Date Duration: 14 hours

What Happened:

After texting throughout the holiday break we finally met up for the awaited second date. We met up at Amsterdam Billiards for a few drinks. I knew he was kinda drunk on the first date but I didn’t realize just how far gone he was because he did not remember how much he told me about his ex among other details. I found out he was a frat guy back in college which makes so much fucking sense since he now works in sales. Typical douche.

After taking some shots, we walked over to Fat Cat Lounge to continue drinking. Conversation was good but he kept using his phone. I’m 90% sure he was messaging his roommate on Snapchat and I glanced over to see “Bring her over!”. 2 minutes later we kissed and headed to his place in Brooklyn. Coincidence? I think not.

A little back story here. I had a really good feeling that we were going to fuck however, my period came back from the dead after being nonexistent for a year. After googling all the things online, I took a shit ton of aspirin and popped in a Soft Cup for the first time. No lie, little weird but insertion wasn’t as complicated as expected. Would recommend.

We made it to the apartment and he put Bob’s Burgers on. (Also, this is when I found out his apartment had no heat or electricity. There was hot water, the TV and a lamp were hooked up to something, but no other lights worked.) Within 3 minutes we were making out and I was on top of him. We moved upstairs and started making out on the bed. Clothes quickly came off and we had the absolute worst sex in the entire world. This asshole didn’t do any foreplay. Like any. To the point that when I asked for an assist he went, “Why? You’re not wet?”. (This had to have been why his ex dumped him)

He maybe ate me out for one minute. Having me on bottom wasn’t working so he asked if I could go on top. Things were fine-ish considering I was dry AF. We stopped for a little bit once we realized the condom broke. I had one in my bag so he got it and made some comment like, “Do you always have condoms in your bag?” If I plan to fuck, yeah. That shouldn’t be weird.

I gave him a sad ass hand job, blew him, and we started having sex again. It was straight shit. He asked if I came and I said no. I wasn’t going to reward that garbage fuckery.

He apparently finished (I have a feeling we were both over it) and he asked if I’d join him in the shower. Okay, fine. But he like actually wanted to shower. I kept trying to make out and get some sexy time but it wasn’t working out. He turned the shower off and hopped out for a towel. Since it was a wash at this point, I did pee in his shower out of sheer spite (also since there wasn’t electricity I wasn’t confident in my ability to find the bathroom later).

We changed and I heard my name being called. (Let it be known that he didn’t offer comfy clothes so I changed back into tight ass jeans and a sweater). He wanted me to meet his roommates. WTF. I said hi and we all went downstairs. He went out to get pizza which left me with the roommates. It was as awkward as you think it was so I focused on petting the cat. When Pete got back, the roommates chowed down then went upstairs. He then put X-Files on and fell asleep in 5 minutes. I took a quick power nap and when I moved to leave he pulled me in so we cuddled and napped for a bit longer. I woke up and tried to move again but as I started shifting out from under him he woke up and said we’d go to bed.

I didn’t sleep the whole night. It was a new place, I was already super uncomfortable, he lived next to the expressway so it was super loud, and I was freezing my ass off. Throughout the whole night, he didn’t say anything to me and only put an arm around me twice for a few seconds. We were not going to be dating, but if you don’t kick a girl out immediately you have to cuddle with her. Also if you have no heat you should probably give a bitch a blanket or something.

Around 8:30 am I couldn’t take it anymore and I called a Lyft to go home. I didn’t say anything to Pete on my way out. He appeared to be sleeping and I was over the whole thing.

I felt stupid though. When my period came through I couldn’t help but think that it was a sign for me not to have sex with him since I already knew he was a player and had feelings for his ex but I ignored it. I’ve never been one for casual sex but I always wanted to see if it could be for me. Universe said it wasn’t.

On the way home I couldn’t help but think about the broken condom. He definitely didn’t finish but I did not want to get knocked up with his kid. I’ve had condoms break several times before but I knew that if I ever needed anything the guy would step up one way or the other. I couldn’t say that for Pete so I made the decision to get Plan B.

To top the night off, when I got home to change my clothes I noticed my jeans ripped down the middle of my right ass cheek. Greattt. Good thing I wore a long sweater that night. He also left a big ass hicky on my neck. Don’t remember when that happened.

On the way to Duane Reade, a DOT worker stopped me to tell me that I was so beautiful and someone should be driving me around since it was so cold. At this point my hair was in its natural texture, my make off was off, and I definitely had VPL. I almost cried on the sidewalk. It made my day.

I wanted to be alone more than anything that day and for whatever reason I felt embarrassed. The sex was the worst I ever had and I knew the whole thing was a bad idea but I wanted to be this strong, independent, sexy woman that I wasn’t. At least, not in the way I was trying to force myself.

If this night taught me one thing it’s to stay true to yourself. It’s okay for people to have casual encounters, take Plan B, and spend $40 on a Lyft. At the same time, it’s okay if it’s not for you. Always stay true to yourself…and maybe wear leggings more often so your ass doesn’t bust your jeans.


Encounter #1.1: The Mama’s Boy

App: OkCupid

Name: Derek*

Date Location: Swanky bar in Herald Square known for its well-crafted cocktails

Location Review: 3.5 Stars-Nothing too too amazing considering the prices

Date Duration: 1 hour

What Happened:

Prior to our date I was on the fence about Derek. To start, after he had asked me for my number on the app he called me almost immediately. Sir, I don’t know you. Don’t call me. I chalked it up to a new experience and maybe it’s just a quirky thing. We texted the whole weekend, he seemed normal, and we went out for drinks later that week.

When I arrived at the bar, I kept looking up at every guy who walked by. Then a young man walked up to me and it was clear that he was my date. Now, I understand with online dating things get hairy when it comes to meeting in person. Some people look like their photos, some not so much. He fell into the latter category. Just overall, not my jam. But I thought, “Hey, Laura you’re being a judgmental asshole. Stop being a bitch, this guy could be fucking fantastic, and get your ass inside.”

We took the 2 seats at the end of the bar with him being on the outside. He worked in advertising, was born and raised in Queens, and was the founding father of his college’s fraternity. Despite looking good on paper, within about 10 minutes I was already done. To start, he had a voice which gave the “I live with my mom” vibe. Then, he kept touching me constantly and put his arm up as to almost block me into my seat so I couldn’t leave. He kept scooching closer to the point I was sitting on the woman in the next seat over. Then, he makes an awkward joke about us not only dating in the future but getting married.

But what sealed the deal was a conversation about ice cream. He asked what my favorite was, I asked him his, and then he proceeded to shit on my flavor. So much to the point that when he got up to go to the bathroom he said I needed to “think about what I had done”.

No. Just no. Upon his return I scooted out so fast as he asked when the next time he’d see me again would be. Because I’m an asshole I left it at “We’ll figure it out”. As soon as I got back to my apartment I deleted our chat and blocked his number. …after sending “the text”*. Not my proudest moment.

You win some. You lose some. Rack em up, let’s play again.


*The Text: The message you send after a date that went poorly or to end things with someone you went out with a few times. Messages can range from “It’s not you, it’s me”, “I’m just so busy right now…”, “I need to work things out with my ex”, and “I think you’re a serial killer”.