Category: The League
Encounter #99.3: Mr. Rhode Island
App: The League
Date Location: Amelia’s Trattoria & Gracie’s Ice Cream – Cambridge, MA
Location Review: 4.0 Stars – Tiny restaurant but food was bomb and the atmosphere was cute.
4.0 Stars – The bathroom is Dolly Parton themed. You don’t need much else.
Date Duration: 3 hours
This was a make or break date. Elias and I hadn’t kissed yet so tensions were high. Also, he wasn’t really bringing it on the texting so that wasn’t helping his cause.
We decided to go to an Italian spot by him and it was nice. Only thing is it was hot as balls and their AC broke. We chatted and conversation was okay. An old couple was definitely listening in on our ENTIRE date but, it wasn’t anything exceptional. About an hour in I realized he didn’t ask me anything. It was really just him going on and on about god knows what and then us splitting the bill so I was out $60.
It was getting stupid hot in the restaurant so after dinner we decided to walk around a bit and get ice cream. We were in a secluded area. Nothing. No lean in. No kiss. Just held my sweaty hand.
We got a little closer to the train station and he invited me to go back to his apartment and that he would drive me back later. Did I want to see if there would be anything? Yes. But, I wasn’t about to be stuck in his apartment when I didn’t even know if he was a good kisser. Need an appetizer before going all in on the main course, ya know?
He was fine with it and walked me to the train. We hugged twice and he talked about how next time he’d come by me. I never texted him back and it died naturally.
Encounter #99.2: Mr. Rhode Island
App: The League
Date Location: Ward 8 & Arya Trattoria – Boston, MA
Location Review: 4.0 Stars – Romantic atmosphere and drinks and apps were tasty
4.0 Stars – Solid-ass Italian. For being in that main drag in the North End, it’s actually good.
Date Duration: 7 hours
I was legitimately excited to see Elias again. It had been a minute since I had someone plan real dates and I just thought he was so cute.
We decided to get drinks and a snack before dinner and based on how he was dressed and smelled that night, I wanted Elias to be the snack. Like damn. Boy came to play.
He was super sweet. Before I got there he tried to get us a table in a more romantic spot and he pulled my chair out for me. Definitely giving gentleman vibes.
Talking with him was easy. There weren’t really any awkward silences and we just shot the shit. After drinks, we headed over to the next restaurant for dinner and that’s where it started getting a little weird.
Out of nowhere, he asked me if there was a political issue I was passionate about. Considering I had just dumped someone for their beliefs, it was odd timing. But, we were on the same page so that was fine.
After we finished dinner, we decided to walk around and found ourselves at the waterfront yet again. And that’s where things got a smidge weirder.
We had both dated married Brazilians before so I told him my little story that ended with me getting a (CURABLE) std. Is that too much to share? Maybe. But if you don’t think that shit is funny, you aren’t the one for me.
To make me feel better, he said he’d share something embarrassing. But then it was this weird stream of consciousness about how he smokes weed, but he has herniated disks in his back so it’s fine, but it’s not an addiction, and he hasn’t smoked in a month because his job tests and he’s looking to switch positions, and he’s looking at moving to LA to work at that office, but he doesn’t know if he wants to work in chemistry anymore, and he already resigned his lease, oh and he has ADHD. I had no idea wtf was happening but it was just a pile of word vomit.
Despite that, I had a good time and wanted to see if we had any chemistry. We held hands but, would there be a spark? We were all alone by the water. Drinks had been flowing. NOTHING.
It was late so we called the Ubers and I leaned into him trying to make something happen. He was oblivious. He kept saying how he wanted to see me again so figured I’d let it slide and wait for that slow burn.
Encounter #99.1: Mr. Rhode Island
App: The League
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
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.
Honorable Mention: Love Refugee
Encounter #62.1: Lake Lovin
App: The League
Date Location: Lake access point – Laconia, NH
Location Review: N/A
Date Duration: 1.5 hours
What initially drew me to Ian was that he was also from New Hampshire. Throughout all my time in NJ/NYC I had only matched with one other guy from NH and it didn’t go anywhere. I was getting really done with NYC guys and I was craving a piece of home.
He also picked up on the NH connection and we exchanged numbers pretty quickly. Only thing was that Coronavirus had just become a thing so that was a buzz kill. However, we were both quarantining in NH.
For the first few weeks of quarantine, we would text over the weekend to try to hang out but it would never work out and then we’d just repeat the cycle the next week. After completing our 2-week quarantines and having schedules that matched, we made moves to hang out.
He lived up by the lake region and his parents’ house was only a block from the water. He sent me the GooglePin and I drove up to the access point.
On paper, this seemed like a good idea. We were outside, the lake looked beautiful and we had both packed alcohol. Problem was it was windy AF and kind of cloudy so it was fucking freezing.
Ian was a smart one and packed a blanket so we sat next to each other huddled up underneath. We chatted for a bit and it was fine. He worked in real estate and was raking in mad money. So much that he was not eligible for the $1200 stimulus check, could shell out $3000+ on rent, and flew everywhere. For real, this kid went international on like 7 bachelor parties in the past year and said he dropped at least $3000 every trip. Meanwhile, I eat food that has been in my fridge a questionable amount of time just to avoid buying something.
Ian didn’t have much to say. The only noteworthy thing was his worst date. Basically he met up with this girl and the texting was great but she didn’t deliver in person. She also ordered the most expensive things on the menu. What got him though was that he looked down at her leg and apparently her calves were hairless but her thighs had thick, dark hair and that was what did it for him. Weird. Overall, he was nice enough but there were so many long pauses. I didn’t feel like I was carrying the team but, I did feel that I was too out there for him.
After about an hour I really had to pee and we realized there was no bathroom. As much as I don’t think Ian would have cared if I peed in the woods, it was just too damn windy to risk it. He walked me back up to my car and I was very surprised that he went in for the kiss. Pretty sure I owe that to him not seeing a girl in weeks but fuck it, I needed it too. It was quick but wasn’t bad. Given everything going on we couldn’t really make out.
I sped to a supermarket and had the most religious piss of my life. Like wow. What dreams are made of. What a time.
Encounter #52.1: Tennis Guy
App: The League
Date Location: Lucky 7 Tavern – Jersey City
Location Review: 4.0 Stars – Definitely a dive bar but has a really cool feel. Lots of band posters and stickers all along the walls and a solid ass happy hour menu.
Date Duration: 3 hours
I had downloaded The League (AKA the most pretentious ass dating app in all the land) around the time of the break up. It’s tough to match and no one ever sends messages so I was surprised that Gareth even started a conversation.
He seemed like a fun guy. Conversation was easy over text and as it turned out he lived in the building attached to the one I nanny in. All about convenient fuckery. He worked in finance but definitely wasn’t one those those douchey bros in the Patagonia vests.
I agreed to a date and we checked out a dive bar that neither one of us had gone to before. He was waiting for me outside and I was a bit disappointed. He was cute but was more petite than expected. Another one that I could have benched. Fuck it, I was already there. May as well see what happens.
Conversation with him was as easy in person as it was over text. He not only gave decent answers but he also asked decent questions. WHAT A CONCEPT. He had an interesting background. He went abroad for his graduate degree and while he was there played professional tennis for a bit. Casual. He also offered to split an app so I was a happy clam. Imma get dirty on some popcorn chicken.
We had been drinking for a few hours and it was time for me to go home. Gareth walked me to the train and we made loose plans to see each other again. We kissed, nothing too crazy and texted a bit over the days following but nothing ever came from it. To be honest, I was fine with it. I had a great time but, physically speaking it just wasn’t there for me and I was afraid I would have led him on. Back to the drawing board.
Honorable Mention: The People v. Larry David
Context: I don’t know what it is but, every man ever on dating apps mention Larry David. ALL OF THEM. And every single one thinks he’s the first to have come up with it.