Encounter #100.4: Rain Delay

App: Coffee Meets Bagel

Name: Mark*

Date Location: Flander’s Field – Hanover, MA & Vitamin Sea Brewing – Weymouth, MA

Location Review:  3.0 Stars – It’s fine. German beer hall that you can bring your mom to

3.0 Stars – Like any other brewery ever

Date Duration: 20 hours

What Happened:

To figure out whether or not I really liked Mark, I agreed to go out with him again. I couldn’t say no. He planned a whole day and even offered to drive since I would be on the road the rest of the weekend.

We went to a bar that he hyped up so much. It was suburban af. Maybe I’m just a bitch but he just hadn’t seen anything in life.

Eventually we made it to a brewery and the conversation was mostly him talking at me about political things. Yes, we had the same views but literally everything we talked about was so fucking serious. I just wanted to crack jokes and have witty banter.

We went back to my place and ended up having sex. It was meh. Then we cooked dinner and he was so sweet. Did the dishes and everything. Maybe it was fine? Maybe this was the best it would get and I should just deal with it.

He stayed the night and I kept avoiding doing anything physical. We hung out a few nights later for my own peace of mind and I was just miserable. I texted him a few days later to end it and at first it seemed that he took it well. He was sad, but didn’t fight with me.

A few days later he asked if we could be friends with benefits since we had “such good communication and sexual chemistry”…no. I declined and we never spoke again.

Encounter #100.3: Rain Delay

App: Coffee Meets Bagel

Name: Mark*

Date Location: Quincy Quarry & Crossing Nines – Quincy, MA

Location Review:  N/A

4.0 Stars – Definitely a hidden gem outside Boston. The patio gives a whole view of the Boston skyline plus the food is actually good.

Date Duration: 14 hours

What Happened:

I knew I liked Mark after our last date but, I wasn’t sure how much. That said, when he asked me out again I agreed so I could get a feel.

He suggested heading up to the quarry and hiking around a bit which I was immediately turned off by but, he said he would bring alcohol and snacks so I went with it.

Despite the fact it stank of puberty and weed, the view on top of the rocks was pretty nice. He brought his camera and we took some pictures while chit-chatting. He did keep touching my leg which for whatever reason, made me low-key uncomfortable. I couldn’t explain it but, I just shrugged it off as we were in public and I was still getting used to him.

Since the golf course was right there, we decided to head over for dinner and everything was normal. Nothing exciting to report. Although, he did tell me that the reason he didn’t kiss me on the first date was because he had a boner the whole time and didn’t want me to feel it. Thank you for sharing?

He invited me to his place and I figured I might as well check it out. Well as expected, it wasn’t long until we were hooking up. We didn’t have sex. Actually, I kinda felt myself trying to get out of any intimate contact with him. There wasn’t anything wrong “per se” but something wasn’t right.

I dipped out fairly quickly in the morning. I knew something was off but, everything else was good on paper so I decided to see him again to really be sure.

Encounter #99.3: Mr. Rhode Island

App: The League

Name: Elias*

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

What Happened:

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 #100.2: Rain Delay

App: Coffee Meets Bagel

Name: Mark*

Date Location: The Clam Box – Quincy, MA

Location Review:  2.5 Stars – It’s pretty meh but you’re near the beach.

Date Duration: 14 hours

What Happened:

Mark and I were both busy so it was a minute before we could meet up but he was consistent with texting me and staying in contact.

I had to dog sit so he suggested we head to the beach so I could bring the dog and we could walk around. He did suggest 10am which was so aggressive but, I would live.

He walked up looking cute and he had a little cooler backpack with him filled with water and treats for the dog which was very sweet. So we walked around and shot the shit. Conversation was much easier this time and it was very clear that we had similar political views which was nice. Mark was also pretty smart so we had more intellectual conversation than I expected.

It was hot out so we decided to take a break and grab some drinks while the dog cooled off. He made a few flirtatious jokes which was unexpected. I couldn’t get a read on him at all up until that point so it was nice knowing that he found me attractive.

I got a text that the owner was on the way so I offered to continue hanging out and have a quick side mission to my place to get the dog situated or, we could go about our days. He chose the side mission.

After the dog got picked up, we threw something on Netflix so we could cool off in the AC. Then, as expected, things started happening. I told him straight up we weren’t going to fuck. It was a second date. I didn’t know him. He agreed to those terms.

Clothes came off and things were meh. He kept trying to talk dirty to me but it was more conversational and honestly just annoying af. Stop talking to me and just eat my pussy.

We hooked up on and off for a few hours but despite agreeing to the terms and conditions, he kept pushing to fuck. It got to the point I had to bring up that my new birth control wasn’t all the way effective yet. He responded with, “Well I have condoms”. SIR. The answer was no. I don’t know what else you need to hear. He apologized between rounds so I let it slide but, it was definitely something that went against him.

Eventually, we ordered food and he ended up staying the night. I wasn’t 100% sold but, he was nice enough and checked other boxes so I figured I’d see where it went.

Encounter #99.2: Mr. Rhode Island

App: The League

Name: Elias*

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

What Happened:

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 #100.1: Rain Delay

App: Coffee Meets Bagel

Name: Mark*

Date Location: Crossing Nines – Quincy, MA

Location Review:  4.0 Stars – Definitely a hidden gem outside Boston. The patio gives a whole view of the Boston skyline plus the food is actually good.

Date Duration: 3 hours

What Happened:

I never meet anyone off of Coffee Meets Bagel but somehow, it happened with Mark. Conversation wasn’t particularly any which way on the app but he asked me out and I didn’t have a reason to say no. What sold him though was that not only did he give me a specific plan for the date, he also included a rain plan. My Type A ass was thrilled.

He was taller and cuter than I thought he’d be. Very blue eyes and had to be at least 6’1″. I had to give it to him. The date he picked was nice af. We were there around sunset and saw the whole skyline light up.

Mark was a nerd in all senses of the word. Worked in IT, loved board games, and had a passion for history I don’t think I’ve ever encountered. Like he knew every single everything when it came to the state of Massachusetts.

Family seemed relatively normal. He was from MA, went to school there, and didn’t want to leave. Weird to me, but okay. Was going through a bit of a weight loss journey so it didn’t seem like he knew he was cute which is always a plus. Also super liberal which I am always down with.

He talked my fucking ear off until about a beer and a half in. Because he was so nerdy, I wasn’t sure if that came from not being able to hold a conversation or that he was nervous. As the night went on, looked more like nerves.

We ended up closing the bar down and he walked me to my car. I wasn’t sure if he had a good time. Yeah he paid but that doesn’t guarantee anything.

I was kinda expecting that we would kiss but then again, you can never count on it. I miscalculated. We hugged and I went on my way just very confused as to wtf happened. He was nice. I had a decent time. But wasn’t sure where he stood.

By the time I got home I got a text saying I was beautiful and that he wanted to go out again. Guess I did okay.

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 #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.