Q.
In the Spring, an ex-boyfriend from 13 years ago struck up a 3 a.m. conversation with me on Facebook Messenger. Over the years, he has reached out to me about hooking up or going to our high school reunions together.
I was the first woman he dated after divorcing his wife after 20 years of marriage. This time I listened to what he had to say. He said he always appreciated my intelligence as much as my good looks, and that he’s been searching for the right person since he moved to the South six years ago.
He said he always felt like we has unfinished business and wanted to try again. So for four months, we messaged daily. He begged me to agree I wouldn’t sign a lease where I am until I visited him. (I’m in the process of moving out of living with my boyfriend of seven years.)
We decided to meet on neutral ground (Rhode Island) in August. I honestly thought we’d have more chemistry in person. It was awkward, and I left after two nights feeling let down. We are still messaging daily with plans to meet again. Should I give it another chance?
– Awkward
A.
I can imagine it was awkward. What high stakes!
This man is asking you to put off signing a lease, but it’s been years since you’ve been together. You need more time, and you can’t do this on his schedule.
My advice: chat with him, try another visit, but sign a lease where you are. Set up a nice home and spend time with friends. Date locally – if and when you’re up for it – because you probably want some new experiences, and it doesn’t have to be this ex or no one.
Be honest with this man about all of it. You can absolutely say, “That trip felt more awkward than I thought, and there’s too much pressure on this to work. I’d like to find my footing as I get to know you better – at a reasonable pace.”
That spirit might make a second visit far less awkward.
One last thought: I understand why you chose neutral ground, but it might be better to see him where he’s comfortable. Get a sense of where he buys coffee and what he likes about his neighborhood. See what’s in his fridge.
No offense to Rhode Island, but it might not be where the two of you feel like yourselves. It’s probably difficult to relax if you’re googling restaurants you don’t know, staying in an unfamiliar hotel, and trying to navigate whatever is happening on I-95 and 6/10 Connector. All that breeds is confusion (for me, at least).
– Meredith
Readers? Was there too much pressure on this trip? Worth a second? Interesting that he went from hookups to asking for bigger things?