When He Wants To Be Friends With Benefits

Hi I’m an 29 year old female I met a guy (who is 40) through online dating, we chatted a for a bit. We exchanged numbers and talked for a couple months. We stopped talking for a while and out of no where he texted me and we picked up where we had left off. ( I would say it was 6 months) we talked and we finally met up had a few drinks talked and yes we ended up hooking up. I did tell him what I was looking for from the beginning of when we started talking again. He told me and I quote “ idk if I am ready for anything serious though. I’ve got too much to get stabilized in my own life before I can give anyone the attn they deserve :/, I promise to always be open and upfront about what going on up here” (in his head) to which I told him ok just know that I’m still looking for what I want (which is a relationship). We talk all the time we hang out once a week, it’s always been like that, there’s a connection for sure. I just don’t know what to do next. We continue to talk and hook up and now I have no clue what to do. I keep telling myself maybe he will change his mind and we can become something more than just a hook up. Help!!! What should I do??? Should I drop the fellow, I mean you would think someone who is 40 will know what they want. Help.

My introduction to the Friends With Benefits concept was through Seinfeld. Elaine and Jerry decided that they could do “this” (have an existing friendship) and “that” (sex without strings) as long as there were some ground rules. First, there were no phone calls after 5pm. (It was the early nineties. There was no internet.)  Second, sleepovers were optional. Of course, because Elaine and Jerry had previously dated, the lines became muddied very quickly.

For me, the take-away of that scenario was even with the most solid and respectful of friendships, once sex gets involved, navigating these arrangements isn’t easy. Lines become blurred. Expectations develop.