Encounter #99.1: Mr. Rhode Island

App: The League

Name: Elias*

Date Location:  Shore Leave & Trillium Brewing – Boston, MA

Location Review:  4.0 Stars – I’m a sucker for a tiki bar. Fun snacks but can’t judge the sushi

4.0 Stars – They have peach beer and solid snacks. Also the patio is really nice.

Date Duration: 7 hours

What Happened:

I was just as shocked as you are that I got a date off The League. I’ve had it for years and have only ever met up with one other person. So the fact that Elias even started a conversation on there was enough to pique my interest.

Chatting with him was fairly easy. We weren’t up each other’s buttholes by any means but it was a decent conversation. He asked me out but also made me pick the place. I didn’t necessarily love that but whatever, I’ll live.

We decided to meet up at 5 p.m. which now looking back, was very early. When I got to the bar, it wasn’t open so I couldn’t find it and Elias ended up coming to find me. (It’s underneath a parking garage so heads up on that).

He was cute. (Also very sweet about me getting lost). We got to chatting and he was one of those people who could shoot the shit. We covered the basics (from Rhode Island, works as a chemist, has a younger brother, went to FUCKING BROWN for his master’s, college basketball fan, in the middle of weight loss journey). But we also talked about god knows what for an oddly long time.

Elias was also kinda funny and sweet. Out of nowhere, he said, “I just want to thank you for going out with me even though I’m only 5’9”. My heart. Then later he said I looked about 25 and it must be whatever I do in the gym. Nothing. I do nothing and it’s clear. But thank you for gassing me the fuck up.

We were having fun and he offered to go somewhere else since it was early. He had lived in the city for over 5 years so he knew the scene. We jumped in the Uber (that he paid for) and headed over to Seaport.

Here we found out that we had both dated married Brazilians before so that was a fun thing to have in common. And we just didn’t shut the fuck up. The next thing we knew the bar was closing down and we had to go.

He asked if I had ever been to the waterfront. I fucking lied. I knew what that meant. He wanted to make out and damn it, I was ready.

Well, we got there and everyone and their mother had the same idea. We sat on some random slab of granite and some couple sat next to us. It felt like he wanted to but I wasn’t going to push it.

It was late so we had to get back to catch our trains. He did hold my hand the whole way which helped confirm that he liked me. Never know these days. A few blocks from South Station he threw in,

“I really had a good time. I had a lot of fun with you.”

“Same! Was not expecting that. Never know how it’s going to go but I’m happy we met up.”

“You’re beautiful. Smart. Have a good heart. Can’t go wrong.”

Ummmm if he was trying to get me pregnant, that was the moment.

We lived on the same train line just opposite ends so I was preparing for a train station make-out. Instead, we hugged and he asked for my number. I mean I’ll take it.

And then we made plans for our second date.

Encounter #98.2: Peabody

App: Tinder

Name: Omar*

Date Location:  Speakeasy and Irish Tavern (No idea wtf the names were) – Sommerville, MA

Location Review: N/A

Date Duration: 14 hours

What Happened:

Even though we had just seen each other the night before, we were both excited to go on an actual date with each other.

Omar beat me to the bar but since I can’t park for shit, he jumped in my car and helped me find a spot (and paid for my parking). Immediately we were holding hands and it was nice to feel coupled up for once.

He made reservations at a speak easy and we were the only people in the place so it was truly just the two of us. Conversation was still decent. Not as free flowing as the night before but considering we had been talking to each other every day for 4 hours at a time, we still found things to chat about.

The bar wasn’t really doing it for us so we decided to leave. He wouldn’t let me pay but I saw the tab. $100+ and he didn’t flinch. I guess he was not lying about making 6-figures in IT.

The next bar I got a little more insight into him. I don’t know how it came up but, we talked politics and we were just not aligned to say the least. It was weird. Socially we were on the same page but it just didn’t make sense to me why he voted for the way he did. Republican I can handle but based on the things he said, the math wasn’t mathing. He kept saying he liked living in MA and what the state was doing. Massachusetts is blue AF. Why are you voting for Trump?

I didn’t know what to think. Maybe I’m just a $n0wfLake liberal but, it was disappointing. Despite that, everything else about him was fine. He could make me laugh and it was clear he was into me so maybe I could look past it? He kept saying he wasn’t *that* political so maybe I could take him at his word?

He came to my place after and we started getting into it. We talked early on about wanting to wait to have sex. He had disclosed to me early on that he had genital herpes and I wasn’t going to be playing with fire if I didn’t know if I even liked him.

The hookup was fine. There was some potential and he seemed coachable but it wasn’t groundbreaking by any means. He would do stuff to me and I would say something like, “Mmm keep doing it like that” and then he would switch it up and start doing something else for whatever fucking reason. Not sure how “like that” translates to stop what you’re doing, but whatever.

Omar was so into me and honestly, it felt really fucking nice. We kept seeing each other and it was nice cosplaying boyfriend/girlfriend. He came over the day after I had to say goodbye to my dog and it felt so good to be able to come undone in front of someone. To not have to carry the emotional load alone for once. I can’t remember the last time a man said he wanted to be there for me while I fell apart and then actually was.

That said, there were some things that happened in the following weeks that I didn’t like. For someone who kept saying they “weren’t political”, he brought politics up an awful lot. Even if I could get over it, I couldn’t see a way for him to be accepted by my friends and family. All I saw were awkward parties and us wanting to raise kids differently.

Speaking of kids, we also had different expectations there. He wanted to be a dad so badly and exclusively wanted kids of his own. I am not sold given the world we live in.

But, what did it was one particular week. We hadn’t seen each other in about 5-7 days. I had called him Monday (No answer) and Tuesday night (he picked up but couldn’t talk). Wednesday he was out with friends, had been drinking and wanted to come over. Not ideal but, whatever. He kept insisting he wanted to see me and was good to drive. Fine. Left the door unlocked for him and ended up dozing off.

At 1am I woke up and he still wasn’t there. Checked my phone and he texted me. When he went home to grab clothes, he ended up smoking a joint with his roommates and fell asleep.

For someone who wanted to see me so badly, it didn’t make sense to me. Was the plan to drive over high and see me while baked af or was it that a substance was more important? Either way, didn’t love the answer.

What tipped me over the edge though was that Saturday night he was at a concert in Boston, wanted to see me, but had done coke and didn’t feel good about driving over. Whatever, all good. We would see each other the next day.

Well, that’s when he dropped that he had gone out with 2 girls since we met. Were we exclusive? No. But, he kept telling me there was no one else. I would make jokes about him having hoes and he would brush it off every time. Do what you want but, don’t fucking lie to me.

There’s an unsaid rule in dating that in those beginning stages, you don’t say what/who you’re doing. But if you’re telling me there’s no one else, all I can do is take you at your word especially after making comments about me having your babies, being at your birthday, and everything else.

I had been on the fence for a while but wanted to see him a few more times in person before I made the call but that pushed me over the edge and I cut it off.

That didn’t go over very well. It ended up being a 4-hour ordeal with him calling me multiple times and blowing up my phone. At one point he Facetimed me, I picked up, and we started talking things over but he was walking into his house and started chatting with his roommates instead while I was on the line…cool. So I hung up and he texted me up the ass.

Apparently what he was trying to say was that he went out with these other girls, hated it, and now just wanted to be with me. Cool. But it still happened. Also, I still vote blue and he still wanted kids of his own. It probably was the right thing to do to cut it off but, I hated every minute of it and kept second-guessing it.

When I woke up the next day, he texted me and asked me to block his number since he knew he would want to text me. He knew where I lived so I kept his texts on mute just to be safe. He texted me three times that week asking how I was but that was it.

It’s been a few weeks and I still feel weird about the whole thing. In the long run, it was probably the right decision but, it also feels so bleak out there. I don’t feel deeper connections often and I may have pushed someone away who would have given me ~70% of what I could have wanted from a partner. But is ~70% enough at the end of the day for a relationship to go the distance?

Not for me.

Encounter #98.1: Peabody

App: Tinder

Name: Omar*

Date Location: State Beach – N/A

Location Review: N/A

Date Duration: 3 hours

What Happened:

I was in the airport coming back from a work trip and for whatever fucking reason, I decided to open Tinder and respond back to a guy from MA. Seemed cute enough. Flight was delayed. Had time to kill. Fuck it.

We kept messaging. And then we shifted to text pretty quickly and by the time I boarded my flight I had creeped his instagram back to 2011.

We talked on the phone the next night for almost 4 hours and made plans for an actual date. Thing was, Omar couldn’t wait that long so while he was in Boston, he stopped by my area and we met up at the beach. (Just want to say that yes, I went to the beach alone at night but there were people and it was well-lit.)

I had about 20 minutes to get ready so I put on my 90s aunt best. Biker shorts, crop top, and denim jacket and just hoped for the best. I beat him slightly and didn’t notice that he parked next to me. That was a good thing because apparently, he peed behind his car. (My dad peed on the side of the road on his second date with my mom. This doesn’t phase me.)

There was a weird instant connection with Omar. Both of us felt oddly comfortable with the other. It’s not that we necessarily had a ton in common, we really didn’t, but there was good banter.

Omar lived in Peabody with his uncle and was saving to buy a house. Worked in IT, went to trade school (no debt), loved sports, was in the middle of a weight loss journey (love a thick guy who doesn’t know he’s cute), and very outgoing.

Going in, I didn’t know what he was going to think. We had talked about types and his was 5’2″, petite blonde. I’m a 5’8″ thick bitch sooooo bit different. We went to cross the street to get to the water and I caught him checking out my ass. We were in business.

We made out here and there and held hands. We were both physical touch people so that was nice. It just felt so good to have an arm around me and be able to be affectionate back.

He walked me to my car and we sucked face for quite some time. Basement got flooded. But, I was excited to see him again and that was something different.

Encounter #97.1: IT Guy

App: Hinge

Name: Carlos*

Date Location: The Townshend – Quincy, MA

Location Review: 4.0 Stars – Good food. Good cocktails. Good vibes.

Date Duration: 3 hours

What Happened:

I had to give it to Carlos. Somehow over text, he came off really sweet. Was he the most attractive? No. But he took the time to plan an actual date for us that would be convenient for me to get to.

Carlos worked in something smart. Cyber security or some shit. Was an only child but was close with his cousins. Overall, fairly normal.

The conversation with him wasn’t necessarily the easiest. I definitely felt like I was carrying the team and that he was already putting me on some kind of pedestal. He really knew nothing about me but instead of asking would hold onto those random nuggets he did have.

At the end of the night, he walked me to my car. I can’t park for shit so I was a ways away in a parking garage. I felt bad that he walked me all that way so I drove him to his car. Shouldn’t have done that.

When we got to his car he went in for it and we made out a little bit. He was good, but I just didn’t want to sit on his face.

Sent him the “You’re great but…” text and we went our separate ways.

Encounter #96.1: Snooze Fest

App: Hinge

Name: Joe*

Date Location:  Margarita’s – Waltham, MA

Location Review: 3.0 stars – Standard issue Mexican fare

Date Duration: 3 hours

What Happened:

Joe and I talked for fucking ever on the app. Between traveling, work stuff, and the fact that this fucker didn’t ask me out until a few weeks in, it just took forever.

Truly, the only thing Joe and I had in common was work. We both worked in the same niche field and it was nice being able to talk shop with someone who fully got it. Other than that, not so much.

He loved soccer and would be playing/reffing nearly every night. It didn’t seem like he had many other interests. From the same area as me. Went to college in Mass. Nothing scandalous to report.

We had Facetimed and I felt like I was grilling him so I didn’t expect him to want to actually hang out. Well, he did. Did I want to go? Not really but, I hoped that it would be better in person.

It wasn’t. First off, he looked older irl most likely from not wearing sunscreen during soccer. His hair was starting to thin but he still was trying to pull his hair back into the tiniest, most baby man bun ever seen.

Conversation went exactly as it did over Facetime. Just me carrying the team. When we left we hugged and I expected to not hear from him. Oh no. He liked my energy and wanted to hang again. So had to (politely) shut it down.

Encounter #95.1: Saugus

App: Hinge

Name: Sean*

Date Location: Idle Hour – Quincy. MA

Location Review: 3.5 stars – Barely ate anything so still can’t say how it is

Date Duration: 3 hours

What Happened:

I was feeling a little ballsy so when Sean and I started chatting I did ask him out pretty quickly. I can’t explain it but, MA men like to chat for fucking centuries before asking a girl out and I was over it. If there’s a vibe, there’s a vibe.

Well it was going to be a minute until we could meet up which meant we still had to text. In the 3 days of texting it was very clear this man was boring but, I had asked him out and had to follow through.

In the 3 hours we were out, he averaged about one question an hour. It was brutal. But we kept ordering drinks so I couldn’t tell what the vibe was. Overall, he lived a boring life. He worked in supply chain analytics. Was from MA, went to school in MA, will probably die there. He did mention his family was wealthy which was odd.

When the night ended, we went our separate ways and never spoke again.

Encounter #92.2: Green Tea

App: Bumble

Name: Moises*

Date Location: Idle Hour – Quincy, MA

Location Review: 3.5 stars – I got buzzed and we didn’t eat so there’s that

Date Duration: 3 hours

What Happened:

Going in, I wasn’t entirely sure what was going to happen. But I was mentally prepared to fuck.

Like our first date, there was a lot of lead-up. Actually the day we were supposed to meet up I tested positive for COVID so that only delayed things further and then he was going to be in Colombia. Just super ideal timing.

We texted here and there while he was gone and I was locked in the house but nothing particularly noteworthy. I chalked it up to just the fact that it’s hard to keep a conversation going over text that long when you don’t really know the person.

He offered to come closer to me and we made plans to get dinner. But then at about 11pm the night before he asked to change it to 11am. Ummm K? Weird but whatever. I’ve had stranger things happen.

He met me at the bar and we got right to drinks. No food. Fuck.

It only took a few minutes for him to start touching my leg and start with how cute I am. I mean facts but we haven’t seen each other in a minute and it’s the Lord’s day. Let’s chill a bit.

He told me about his trip and then next thing I knew we were taking green tea shots again. Actually, he asked me if I was the person he took shots with last time. I made a joke about him confusing me with his other hoes. The flustered look on his face. Hilarious.

After about 45 minutes he made some comment about watching a movie with me. I made a comment about he was really gunning to get the invite to my place and we’ll see if he makes it that far. The way this man tried to backpedal. Sir, I know exactly what is happening here. You do not give a flying fuck and just want to get laid. And SAME HERE.

We started making out at the bar and he more or less invited himself over. I was shaved and cleaned the house beforehand. It was going to happen.

There were no games when he came into the apartment. We immediately started making out, he had me against the wall, and then next thing I knew clothes were on the floor and I was laying on the bed.

And then it got kinda weird. He laid me down and I expected him to start working on me. Instead he kinda perched by my face and I blew him. Weird angle to do that but if that’s what you want, fine. Was planning on giving the full Gluck Gluck 5000 but I guess that’s fine too. I was only there for a moment and then he pulled me on top of him. I thought we were going to keep warming up but he went straight to fucking. I asked for an assist but he just laid me down and tried to fuck me there. So I had to explicitly ask for foreplay and he fingered me for a minute or 2.

It was clear this fucker could not fucking wait so I grabbed the condom and we got at it. Thing is that didn’t last too long either. I know I’m good, but I’m not finish in 3 minutes good. I couldn’t tell if he finished or just went soft super fast and was trying to cover it up.

We laid in bed for 2 hours making out and chit-chatting and then he said he had stuff to do at home so he left.

I am a psycho so after he left I went to the bathroom and peeked at the condom in the trash. Dry. Interesting. Hours passed and I didn’t hear from him. Also interesting. I texted him some bull shit asking how his night was or something and he didn’t respond until 11:30 pm. I texted him back in the morning. No response until 11:30 pm. I happened to be up so I fired right back. He haha’d the text. And I was fucking done with that nonsense.

Encounter #94.1: The Dentist

App: Hinge

Name: Martin*

Date Location: Magoo’s Ice Cream – Rockland, MA

Location Review: 3.0 Stars – Decent mini-golf course and good ice cream. Not a flashy spot but it gets the job done.

Date Duration: 3 hours

What Happened:

It’s not that there was a lot of lead-up between Martin and me matching to when we met up. It was a fucking eternity.

We chatted on Hinge for over a month. During that time I went to DC, VA, FL, a wedding, turned 29, and got COVID. Lived a fucking lifetime. Overall, Martin was fun enough to talk to. He had just finished dental school and was studying to take his licensing exam. Lived a few towns over from me and came off normal. So when he asked me to hang out, didn’t have a reason to say no.

We went mini-golfing and he was cuter than his pics would have led me to believe. Very tall, and clearly had a nice body. I kicked his ass at golf and he wanted to keep hanging out so we got ice cream. Conversation was still okay but we were definitely running out of things. We decided to call it a night and he walked me to my car and we hugged.

In the days following the date, I picked up on the fact that he was not a consistent texter which I just don’t have time for. But, I kept thinking back to the fact that he was freaky active. I don’t mean go to the gym for 2 hours a day. I mean multiple spin classes followed by going to a climbing gym followed by a run. So that was weird. Not sure how to decipher that but smells like some kind of disorder.

In the end, I just wasn’t interested in pursuing it further so may have ghosted him and never heard from him again.

Encounter #93.1: San Fran

App: Hinge

Name: Victor*

Date Location: Bartaco – Boston, MA

Location Review:  4 Stars – We just drank so not sure how it is food-wise but atmosphere was nice

Date Duration: 4 hours

What Happened:

It was my birthday week so damn it, was going to be my week of 20-FINE. When Victor asked me to go out that Friday, had to say yes.

Going in, I did think Victor was going to look like an ill, victorian child based on his photos but when I saw him IRL he was really cute. Tall, decent build, no complaints.

We got a spot at the bar and started chatting. Conversation over text was good and it seemed to translate decently in person. He was from San Francisco originally but came to Boston for college so he could play soccer and then he never left. Worked in sales at some 3-D printing company and was the baby in a popular movie I will not share to keep his anonymity.

Tbh I had no idea if he liked me. At one point he asked me how I thought things were going and I blurted out, “The fuck I know. I can’t get a read on if you’re enjoying this or not”. He confirmed that he was and started breaking out of his shell more and more.

He was definitely west coast in that he was way more chill than me. But he had some moves on him. At one point there was a lull in the conversation and he just blurted out that he thought I was so attractive. So that was cool.

He found out it was my birthday week so he wanted to do something fun with me. I wasn’t looking to be out all night so we decided to walk along the water in Seaport. On the way there, he held my hand and then did this flick of the wrist thing to pull me in. Next thing I knew we were making out and it was pretty damn good. We kept walking and when we got to the water took a bench and kept making out. We were those people.

It was getting late so he walked me all the way to the train and we texted here and there the next day. Then it just stopped. And I don’t know if this is connected in any way but, I tested positive for Covid 3 days later. Curious. Very curious.

Encounter #92.1: Green Tea

App: Bumble

Name: Adrian*

Date Location: River Bar – Sommerville, MA

Location Review: 4 Stars – We just drank so not sure how it is food-wise. Was close to a parking lot and faced water so that was really nice.

Date Duration: 3 hours

What Happened:

There was some lead-up on this one. After chatting on Bumble for a bit, we moved to text, and then he had to reschedule once then I had to. Just a lot of delay so had no idea what to expect when we actually met up.

Well, there was an ass ton of traffic the day of, and then FINALLY we fucking met. I knew I had to turn it out and bring the A-game since there had been so much lead-up. So ya girl was cracking jokes left and right at the bar. Apparently so much that Adrian thought I was drunk. Nope. Just unhinged.

But Adrian was a cool guy. Grew up in Florida, was Peruvian and Brazilian, worked as a web something or other at Puma, lived by himself, and played soccer regularly. (Also had this big, bright smile I kept staring at).

Adrian could also fucking drink. Granted, I didn’t eat before I got there so after a margarita I was feeling myself. But we were joking about green tea shots and then next thing I knew 2 appeared and we chased them with another margarita.

He had some time to kill and I wasn’t about to drive like that so we walked along the water and he held my hand. Then when there was a break in the conversation he pulled me in and we kissed (made out). Adrian knew what the fuck he was doing. It was one of those where the world kinda stopped for a second.

We kept walking, I blinked, and then we were in a parking garage going at it in his back seat. Like he was all up in my titties and there may have been a slight OTPHJ. Honestly, if he didn’t have plans after we probably would have fucked. The chemistry was that intense.

Mid make out he asked if he could see me again 2 days later but I had plans. (AKA I had another date) but we established another day. He drove me up to my car, we kissed, and then I went on my merry ass way.