Category: Worst Dates

Encounter #71.1: Guns Blazing

Published on by datinglauraLeave a comment

App: Bumble

Name: Ryker*

Date Location: Tiki Rock – Boston, MA

Location Review:  5 Stars – For being a theme bar, this place is pretty damn good. Drinks packed a punch and food was tasty.

Date Duration: 4 hours

What Happened:

Going in to this date, I was excited. Conversation with Ryker was easy on both the app and text. Also his resume going in was pretty impressive. He was a Master Electrician (hello 6-figure salary and ability to fix shit), owned his own home, had a Burmese Mountain Dog, and was just down for fucking anything. Like really, he suggested a ton of shit for our first date and it was all super fun stuff. Also, he made me a quick playlist and his taste perfectly aligned with mine. Life was good.

He suggested going down to Boston and offered to pick me up and drive me down. Although I appreciated the sentiment, I didn’t want to get murdered. We decided to park in East Boston and then meet take the T to the bar.

This is not a huge deal for me. I take public transit all the time. It was though for him. He revealed in the first 10 minutes of meeting that not only has he never been on a plane, he has never taken public transit. This is weird AF to me. You may be thinking, “But Laura, what if he’s from bum fuck nowhere?” He wasn’t. This kid grew up 20 minutes north of Boston. Super weird. He also went on to say that he grew up extremely sheltered and then kept skirting questions about his family. Interesting.

We got to the bar and he insisted on us actually eating which was super refreshing. I got wined and dined. Drinks, apps, entree, whole thing. Over dinner, the red flags began to pop up. He told me about his job and may have included too many stories about him cussing out his employees. Then there were stories of him telling his friends to fuck off. Kayyyyyy.

I forget what we were talking about but he said, “I don’t like rules. That’s why when Biden got elected I went out and bought a bunch of guns so he couldn’t take them away.”…HOKAY. Lots to unpack here. I get that not everyone agrees with my views on this but, I am not a gun person in general but I know that some people are and that’s fine. However, buying a gun because Joe Biden is going to take it from you is just not a reason I can entertain.

I said something to the effect of, “Ohhh okay. Just so you know I’m liberal AF”. To which he replied, “I’m sorry. This is why I don’t like talking politics. I don’t want to do anything to lose you.” Oh this just got 50 shades weirder. Honey, you don’t even remotely have me. Slow your roll. We’re 40 minutes into our first date.

At this point in time, the City of Boston had a policy that you could only stay at a restaurant table for a maximum of 90 minutes. So please keep in mind at this point in time, I had downed easily 4-5 in under 2 hours.

We left the restaurant and since we were so close to the waterfront decided to walk over and chill on a bench. In the 2-block walk over, several things happened.

  1. He held my hand.
  2. He licked my hand
  3. He said, “Shit. Now you’re going to go home and tell your friends that some guy licked your hand”
  4. I thought to myself, “I am definitely going to go home and tell my friends a guy licked my hand”
  5. We were talking about ventriloquism and how not even an ex I dated over a year had seen the tapes. He then asked how big his dick was. Not sure how those two items were correlated, but it happened.

At this point, I was so happy I was drunk because I have no idea wtf I would have done sober. I imagine the date would have ended much sooner.

We made it to a bench and he thought it was a good idea to lay on me. Just no. We were talking about my job search and moving plans and I said that I wanted to move to Boston. He then asked if he’d have to sell his house. I DON’T FUCKING KNOW, RYKER. SOUNDS LIKE A PERSONAL PROBLEM. Also, I DON’T KNOW YOU.

He kept pressing me on why I wanted to move back and I explained that someone close to me had been raped and I was needed back in the northeast. He then asked if she was drinking when it happened. Excuse me? Then he asked if I had been raped. Double excuse me? On what fucking planet is that an appropriate question to ask? To top it off during this period of time, he kept going on and on about how he wanted to find his forever person and get married. I imagine if you stopped asking women if they’ve been raped and licking their hands, your odds would be much better. But I digress.

We sobered up and got back on the train to get to our cars. Now I don’t know what fucking possessed me but, since it was clear he hadn’t seen shit in his life we walked a little bit in East Boston since you get the best view of the Boston skyline. Once again, he started asking me highly personal questions this time about my last relationship. I mentioned that it was really hard for me because as an anxious person who really needs physical touch, it sucked that my ex never wanted that type of affection which would just make my anxiety worse. Ryker went, “Really? I don’t see that from you. You seem to hate being touched.” Nope. Just by you, my dude.

At this point I figured since he had asked me so many personal questions, it was my turn to prod for funnies. I asked what happened in his last relationship and he really didn’t want to answer. I pushed again. “Well, aren’t I just going to find out eventually?” Check mate.

He started by saying that he really doesn’t like telling women this because then they don’t want to talk to him anymore. Off to a great start. From what I gathered, it seemed like the relationship he had with his ex was toxic in general. He said she would hit him and, “I would never put my hands on a woman but plates were broken.” Jury is out on that one but that paired with the cussing out of friends and employees was the nail in the coffin.

Whatever happened with this girl has bled into other relationships. He was dating someone else for a bit, the ex reached out to this girl to tell her about Ryker, and then that girl broke it off with him. He made a point to say he wouldn’t tell me the ex’s name because once that comes out these things start happening. Feeling V SAFE, rn.

He walked me back to my car and we hugged good bye. By the time I got home I got the text asking how he did and if I wanted to see him again. I felt bad. On paper, the resume was there, the guy clearly wanted to meet that special someone, and he was willing to do anything to get that. But it was a no from me. Nagasaki’ed.

Encounter #54.2: Coast Guard

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App: Bumble

Name: Jesse*

Date Location: His Place

Location Review:  N/A

Date Duration: 2 hours

What Happened:

I was a bit disappointed when I didn’t hear back from Jesse. It dug up a lot of weird shit I had been pushing aside and even though I disagreed, he wasn’t entirely wrong that I had a wall up.

I went along with my weekend and everything was going to plan until that Saturday night. My friend and I were drinking on my couch and I saw a text from him come in asking what I was up to. I left it on read. He needed to sweat.

About an hour later he called. I picked up and it came out why he hadn’t talked to me all week. He was being deployed in less than 48 hours. Fuck.

The reason his medical clearance was so crazy was because they were immediately sending him out on a mission. He tried to apply for leave to give himself time to get his house and everything in order but it was denied. So basically he had spent the rest of that week trying to get his shit together and see his family before he left.

We made plans to try to hang out the next day. He obviously had a lot going on so I wasn’t expecting to hear from him. He called me that morning and we talked for about an hour and he kept saying that he would do what he needed to do so we could see each other.

Several hours passed and I thought that was it. I really couldn’t hold it against him. Deployment is a lot to handle. 10:30 pm he called and said he was coming to pick me up. OH SHIT. It’s my time to shine.

I threw on some semi-attractive lazy clothes and made myself look like I hadn’t lived on my couch all day. When he got me, it just felt off. He, understandably, wasn’t as talkative with everything going on but we really didn’t have any banter. What was a 12-minute drive felt like 30.

The house was nice. Garage, hard wood floors, 3 bedrooms, jacuzzi tub, the whole thing. He gave me the tour and as expected, we started making out when we got to his room. Things were promising. He was a decent kisser and as I slid his shirt off I felt how soft his skin was and that he was ripped. Fuego.

Then shit got weird. So at that point we were both naked and standing. He then went behind me to suck on my neck and attempted to finger me. I mean I saw where he was going but, it probably would have worked better as the method to get my clothes off.

He kept going with it and wasn’t being too aggressive so I took the lead. I got him on the bed and started blowing him. To start, he must have rubbed something on himself before I got there because he tasted so strongly of soap and tea tree oil. It was like licking a yoga mat. On top of that, he was SILENT. No moaning, no words, nothing. This was an area I felt confident in so after awhile I kind of just came up for air and figured he was good.

I then asked if he could work on me for a bit and this fucker suggested 69. Ugh. Fine. He wasn’t very good. If I had to describe it, it was like he was trying to suck the meat off a chicken wing. Plus anytime he was doing something good, I’d verbalize it, and then he’d immediately switch to something else. THAT’S NOT HOW IT WORKS.

He randomly stopped so I hopped off and we started fucking. Things were going well. We were finding our rhythm. But then he stopped again.

“Did you cum?”

“No, did you?”

“I am so sorry. I did. It’s been awhile, I’m so sorry!”

We had been having sex less than a minute.

I didn’t know how long it had been for him but based on how embarrassed he was and what I knew about his last relationship, it had to have been in the year+ range.

We made out a bit and snuggled for awhile. He had to pack so he said I could hang out and watch Netflix for a bit while he threw his bag together. I offered to leave. I knew he had a lot to do but he insisted it would be maybe 10/15 minutes.

I curled up on his couch and after 10 minutes it just felt too weird. I went upstairs to say good bye and he called me an Uber which I appreciated. We never spoke again.

And so with that, I saved America by fucking one of their finest. You’re welcome.

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Encounter #26.1: Not. Fine.

Published on by datinglauraLeave a comment

App: Hinge

Name: Randall*

Date Location: Mr. Purple

Location Review:  2.0 Stars – Overrated AF. The view is fantastic but it will cost over $30 for 2 drinks.

Date Duration: 4 hours

What Happened:

Randall and I didn’t talk too too much leading up to the date (may have convinced him to quit his job though) but he seemed pretty normal for the most part. He did ask pretty early on why I was on Hinge and how long I had been single but he also said he wasn’t one for small talk so I let it go. He would have found out one way or another.

After some back and forth, he settled on a spot. First we were going to Mr. Purple, then he wanted me to go with him to his company happy hour (weird), then he quit his job so he thought it would be weird to go (but not weird to bring a first date), so we decided on Mr. Purple…again.

This place was bougie and overrated AF. I had tried going the week prior but the line was fucking ridiculous. It was one of those spots that you should really only go to for one drink and an Instagram photo. Aside from the view, there was not much else going on. The drinks were expensive and it didn’t seem like it could easily flip to give room for dancing. So you just drink and soak up your rich friend’s awesomeness or whatever.

He was attractive. In shape, nice eyes, muscular. But then he opened his mouth and I wanted to kill him. Off the bat he asked me what my deal breakers were. I said if someone doesn’t share the same political views. I explained that I come from a more “modern family”, I’m liberal AF, and it would be difficult to bring someone in to my life who doesn’t agree with my values. He then went on to say that being gay is a choice, he chose to be straight because he is acting on his own desires, but then back tracked to say that being gay is totally fine and people can’t help it. K.

Then he went on a long ass tangent on guns that made no damn sense, said he didn’t agree with Black Lives Matter, Obama wasn’t that great, and Trump “isn’t that bad”. It’s not necessarily wrong to have these views but, don’t try to tell me you’re on the same page as me politically and then come up with all that.

He also thought he was much smarter/more important than he was. Because he was in the navy, he started college a little later. He said his professors were astounded that he knew about the recession and all this other stuff because he was 24 taking classes. Really? Calm yourself. I’m sure they weren’t all that amazed and it wasn’t that big a deal. I’m 2 years younger than you and I also know about that shit. YOU AINT SPECIAL.

Randall made it clear that he was looking for something serious and wanted to settle down. Thing is I didn’t think he knew what that meant. He said he knew what it took to be a great boyfriend. Uhmmm, he only had one major relationship which lasted 5 months. He also made some comment like, “You seem like you’re looking for something serious. I feel like you make a good girlfriend.” YA. I was only in a relationship for 6 years and 4 of those years were long distance, I’ve been single awhile, and have dated every asshole in a 10-mile radius. I’m not new to this rodeo.

Every time Randall spoke it reminded me of a boy who wanted so badly to be a man if that makes sense. He wanted to seem so suave, confident, and worldly but really he was a boy spitting out hot air. We talked about “the window” when you’re on a date. Like the moment you kiss. He asked how I knew if there was a window or not and I said something like, “If you have to wonder if the window is open or if you missed it, it probably wasn’t open in the first place. When you’re vibing with someone you just know when the moment is right and you don’t have to think.” He then grilled me on if he had missed his window with me. At this point, I just wanted to fuck with him and said that he had a clear shot earlier when we were standing outside. (It was sunset, slight breeze, he may have been annoying but it was romantic.)

He was bothered that I wasn’t 100% into him and then tried to make it SO CLEAR he was into me. He pulled my chair to be closer to him, put his hand on my knee, held my hand, put his arm on my chair with his hand on the back of my neck, and then we kissed. He was a good kisser, but then he would talk and it would be all over.

Randall and I covered sex that night. He was apparently “very good” because he could move his hips separately from the rest of his body, his oral game was strong, had a body count over 60, and he (allegedly) had a 9 inch dick. Thank you. Needed all that on the first date. Oh, and I forgot to mention that HE DOESNT USE CONDOMS AND LIKES TO FINISH INSIDE A GIRL. Okay, just asking to get a girl pregnant. He felt like you only use a condom with a girl you’re not serious with. No. No. No. I brought up that for me it’s non-negotiable. Pregnancy and STDs are a thing and my life has been pretty great so far without either.

The clincher for Randall was in our last hour or so together. We kissed already. Fine it happened. Then he started planning our lives together. He wanted to be “a power couple like Jay-Z and Beyonce” and maybe one day he could meet my parents. He could show me the world of rooftop bars, little black dresses, and fine dining while I would show him the world of dive bars and farming. (No joke. That was said.) He went to the bathroom and asked if I’d come with him. No? I don’t want to hook up in a public bathroom with you. When he got back we kissed again but he got more aggressive. He grabbed my ass (fine), started feeling me up and commented that he could feel that I was wearing nice underwear (less fine), slid his hands under my dress to continue to feel up my ass (not so fine), then smacked my ass. NOT. FINE.

It was time for me to go. He asked how I was getting home. I said that I was taking the PATH train back home. By myself. And he would take his train back home to his place. By himself. Randall said he “wouldn’t expect anything less”. He then threw in that he was going to stay because a friend was meeting him but not to worry, he wouldn’t talk to any girls. I mean I was leaving to get drunk and try to make out with more boys. But whatever helps you sleep at night, Randall.

Within 5 minutes of leaving he sent a text saying “I had a great time tonight!” I left him on read. The next day I figured it was time to send “the text”. I unmatched him on Hinge, crafted my message, sent it, then immediately blocked him. He had read receipts on. Motherfucker saw that text IMMEDIATELY after I sent it. He had an iPhone so there was always the possibility a message would come through on iMessage on my laptop. Fortunately, the coast was clear and I was reminded to block THEN text.

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Encounter #16.1: In and Out Date

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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:

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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.

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Encounter #12.2: A Hanukah Miracle

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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.

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Encounter #1.1: The Mama’s Boy

Published on by datinglauraLeave a comment

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.

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*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”.