Tag: Dating In Your 20s
Situation #11.1: Newsies
One of my childhood friends was getting married and I didn’t know what to expect. I knew some people from his friend group but had no idea who would be there.
Wedding was open bar so I figured that shit out real quick.
My brother was also invited so we were catching up with a friend from home and Ian walked up. Did he look like he was about to sell me a Boston Globe because of his hat? Maybe. But, he was hot and I shaved. We introduced ourselves and when he walked away I asked our friend if this guy was single and would be down to make out with me. I got the yes. Target was acquired.
Ceremony was lovely and it was time to start the reception. The first dance happened and then the DJ called all couples to the floor to join. My entire table got up but I was chilling, sipping my drink. Then I felt a tap on my shoulder. It was Ian.
We danced on and off together throughout the reception but nothing really happened. We did kinda grind up on each other and I saw the groom’s parents watching us from the corner of my eye but it wasn’t so scandalous that I felt the need to stop. Would give them something to discuss in the morning. Ian and I didn’t really talk all that much on the dance floor but when I was leaving for the hotel bar he asked if I’d be there and touched my back. Interesting.
I was chilling with my table from the wedding (shout out to Table 10) and Ian eventually came over. We chit-chatted and I found out what he did for work. (Also may have found out that he broke up with his fiance fairly recently). Then we talked about zodiac signs and death of all things. Some of the guys went outside to smoke cigars and before he stepped out he basically invited me back to his room later so we could “keep talking”. Okay, we will see about that Ian.
(I later found out that my brother talked to him at the hotel bar and asked if he was interested in me. He said he would give Ian his blessing to spend the night with me if Ian let him grab his ass. Ian declined the booty grab, and said he would let my brother watch him walk away.)
Well, he was taking too damn long outside so I went up to Table 10’s room to keep drinking before I went to bed. I was wrapping up when my brother called me. He was in the hotel bar with Ian and apparently Ian was still interested. So Table 10 invited him up.
He took fucking forever again. My brother showed up to the room first drunk off his ass and then 10 minutes later, Ian strolled in.
We shot the shit and he was more interesting than I originally thought. Also, my brother was way drunker than we originally thought. At one point I overheard him telling Ian about how I am a goddess, someone who has “really lived” so he needs to really treat me right later “if you know what I mean”, and that he needs to really go for it. I was being pimped.
It was time to go to bed and since we couldn’t trust my brother to take an Uber to his hotel, it was somehow determined that we’d put my brother in my room and I would sleep in Ian’s. V clever.
Ian was a champ and helped me put my brother to bed. I stepped out to change into comfy clothes and when I came back, Ian was taking my brother’s suit pants off and my brother kept moaning, “Ian! IANNNN!” and then yelled at me to look away so he could, “Live his fantasy”.
Despite the sexual harassment, Ian still wanted me to stay with him. We crawled into bed and it wasn’t long until things started happening. Now, I genuinely wasn’t planning on fucking him. But he was naked, that body didn’t quit, and he was packing so I had a change of heart. Overall, not bad. Would fuck again.
We talked for a few hours and eventually fell asleep. This was also when I found out that my brother told him directly that Ian had “Nice buns”.
I woke up before him having visions of vomit all over my own hotel room so, I may have thrown clothes on and dipped out without saying anything.
I did follow him on Instagram and saw a DM slide in the next day.
Honorable Mention: Words in My Mouth
Honorable Mention: Here we are
Honorable Mention: Mozzarella Ella Ella Eh
Encounter #100.4: Rain Delay
App: Coffee Meets Bagel
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
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.
Honorable Mention: BLM
Honorable Mention: Great American Novel
Encounter #100.3: Rain Delay
App: Coffee Meets Bagel
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
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.