So this girl invited me to her hotel room last night
I’ve known her for years, we sort of “talked” and hung out for a bit at one point and then we fell out of touch for 5-6 years, during which time she got married, left town and started a new career.
She’s my age, 36 and although we shared a mutual attraction I never did seal the deal. She’s beautiful, I always regretted dropping the ball. I noticed on Instagram she reverted to her maiden name so I shot her a message, what the hell. Maybe this is part of god’s plan, unfinished business yada yada.
We chat a bit and she tells me she’s going through a tough time. As I suspected, marriage is failing/failed and she’s currently staying at a hotel. Invites me to come by and have a drink, and of course I immediately got excited and assumed this could be potentially a good opportunity for two consenting adults to have some fun.
As always, I didn’t get my hopes up because I’ve gone to several “hook ups” that didn’t materialize and been disappointed. I still put myself together nicely and took condoms and a bottle of wine.
She seemed pretty excited about me coming, said she was hopping in the shower. Several texts and phone calls later I arrived at around 8:00 pm. I go in, big hugs and smiles. I opened the bottle and poured a couple glasses as she finished blow drying her hair. We spent a good 20-30 minutes catching up, briefly touched on her marriage/breakup and what she was going through. She had bruises on her arm which I asked if they were from him and she said yes. She told me he had been abusive but I didn’t realize the extent or whether it had been verbal or physical.
As a friend I made sure to try and console her and let her get everything off of her chest, however I tried not to dwell on that too much as I wanted to take her mind off of that as I could see how devastated she was and wanted to cheer her up and alieviate some stress, I also didn’t want to be just a shoulder to cry on.
Once we had moved past that stuff we sat on her bed talking for an hour or two. I tried to feel it out and escalate if I could but we weren’t that close together and it’s obviously not easy to discretely get closer but there were a few instances where she layed down next to me to show me pictures on her phone, our faces were pretty close together but I didn’t feel comfortable enough making a move.
I had to work super early so I started to wrap things up around 11 and she tried to get me to stay while she went and got another bottle of wine, I didn’t want to be miserable for an 8 hour shift on the off chance I might get laid. I left on a good note and she wants to hang again, I guess I’m just wondering how to escalate next time/make a move? Should I be honest and up front with my intentions/feelings towards her or just play it cool until her divorce blows over? Or C. Should I just run in the opposite direction as it sounds like a sketchy situation?