I’ve recently reconnected with an old friend. I’m 39f, he’s 55m.

When we met each other a few years ago, I was not single. I liked him, but I wasn’t free, and we eventually stopped talking.

I moved, got married, and had a kid, and got divorced.

Since the divorce (2 years ago) I’ve started doing occasional freelance work in the old area. I ran into him in the bar where I first met him, very unexpectedly. I asked if he would like to go to an event with me, and we did, and had a great time. Then he invited me to a cookout with our mutual friend, and again, a very good time. Although he does seem to be very nervous around me until he’s had 2 glasses of wine. He even briefly held my hand after several drinks. I’m not sure how to take that. Maybe he just gets mildly amorous with alcohol?

I like him a lot though. I always have. I don’t know if we would be romantically compatible, but I would be open to finding out. I also would be ok with being friends. We do live about 2 hours apart from each other now, and I have a child.

With all of that backstory, does it make sense to let him know I’d be open to exploring more than just a friendship, if he wanted to? I know we’ll be attending an event we were both invited to in a couple of weeks. I don’t want him to feel awkward about going, so maybe I should wait till after that?

What would you do? Would you appreciate someone letting you know if they were interested in you romantically, or would it make you feel awkward to be around them?

2 comments
  1. I assume he becomes more confident when he has a few drinks, and he has held your hand which tells me that he wants the physical aspect.

    If I were him, I’d want the woman to tell me if she is interested in me. It would make life a lot easier.

    If you’re keen on exploring more, just ask him out on a date. Make sure you use that word too, so he doesn’t get mixed signals.

    Enjoy and have fun 🙂

  2. I think stating it in words, at this point, might be a little awkward. Why don’t you continue just being at events together and see what develops?

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