I matched with Tom on The League. He had more on his profile than most do; a list of goals with some humor embedded. We quickly connected over doing something spontaneous, but then I realized he didn’t live in Boston, nor did he work in Boston. What a fraud. He lived over an hour away. I didn’t want to meet halfway, and I felt bad having him come to me. It felt like a waste of time for both of us. Even though we had an engaging start to our convo, I was sure upon meeting that there wouldn’t be a connection. I’m not too optimistic these days when it comes to first dates. Then Tom suggested going to Newport, Rhode Island. I asked for a few more details and agreed. I had the day off, so why not spend it somewhere new?
We decided to meet at 2:00 in the afternoon, but I still didn’t have a clear picture as to where. After getting stood up twice recently,1 I expected a clear plan with a day, place, and time. Tom said he got a hotel for the night, so I could meet him there. “What are your intentions?” I asked, and he responded to MEET there. I waited for him in the valet section outside the lobby. He came down from his room, hugged me, and then we were off to our first location. The plan was to hop around a bit, and not stay in one place.
We first went to a lobster bar, drank a beer, and split two appetizers. After that, we grabbed a margarita. Then another beer. He knew the area well, but still asked for my opinion when choosing the next spot. I got a notification from work that I had tomorrow off too, so I decided to stay longer than planned. Tom offered that I stay over and I accepted because we were having a good time – it felt natural.
We ordered oysters and he reminded me that they’re an aphrodisiac. Then Tom told me his sister-in-law was on her way to the hospital to have a baby, and our conversation went something like this…
Me: How many kids does your brother have?
Tom: This will be his second
Me: Do you have any other siblings?
Tom: Yes, I have a younger brother who also has two kids.
Me: How many kids do you have? Just kidding around.
Tom: Two
He then blurted out that he’s divorced and hates his ex. He knows he should’ve put that on his profile or said something earlier. Blah blah blah, seems to be a trend this summer.2 But it didn’t change the trajectory that night. We ate dinner together then stopped at the hotel bar, where he grabbed two beers to bring back to the room. I asked him to get me a toothbrush, which he stole from the lobby (his profile did state he was a rule-breaker).
We spent the night together and in the morning he was passed out. I knew I had to get back to Boston, so I woke him up before I left. Nothing exciting happened then or since. I went on this date telling my friends “I’m in my Newport dating era,” when in reality I’m back in my dating daddy’s era.
My only regret is not getting that hotel lobby breakfast.
- Read for context Stood-up Summer ↩︎
- Similar to Emery in “I have a couple of kids” ↩︎
Single at 30 