I'm not sure whether I'm "doing fine", or whether I'm regressing into my "beta" habits.

I just turned 32, and I really don't have many friends. I would say there are two that I very occasionally might hang out with, although they're not exactly social peacocks, either (one of whom is married, and his wife has him on a pretty short leash).

About a month ago, totally out of the blue, a woman I used to be friends with reached out. The story here is she I knew her through another friend, when her ex lost his fucking mind about two years ago, she asked me for help because she didn't have anyone else to turn to (initially just keeping her safe while he was stalking her, to helping her navigate the legal system to get a protective order, and finally helping her move).

At least that part, I don't have any regrets. It feels good to help someone out who genuinely needs it.

A few weeks after that, I'd asked her out properly, but she turned me down. I went out exactly one time with her and her new BF, it was painfully awkward for all parties, so that was just kind of the end of that.

Anyways, so she reached out recently. Since then, we've gone out probably 5-6 times, in one case it was literally an all-day affair of going to bars, then finally going to dinner.

So here's the thing; I know that right now, this would be "orbiter" territory. And hell, maybe it is. But I'm also not really investing anything here; I honestly just like having a reason to go out with anybody, and honestly, she's pretty cool. We have interesting conversations, it's not like I'm going with any hope of "sleeping with her" (even if I totally would, if she ever expressed interest).

But still, maybe I'm undermining myself in some way without even realizing it?

As far as I can see, just trying to weigh things out in Pro's or Cons...

PROS:

  • Often seen with a staggeringly gorgeous woman maybe raises my SMV

  • Hanging out with her gives me an opportunity to get out and socialize, when I might otherwise just be staying at home

  • She's a local, so she's introducing me to a ton of great spots I would have no idea exist, which is not only fun, but gives me more places to suggest meeting with others

  • Maybe this is a "con", but it honestly does feel really nice to spend time with people. She's just enough of an asshole she can make me laugh, and I'm probably just a bit starved for spending time with someone, especially since most folks my age are already married home-bodies

CON's:

  • This could be a cut-and-dry case of "orbiting".

  • Just like spending too much time on social media, there's a risk that I'm feeling more "accomplished" than I ought to. If I'm spending time with a beautiful woman, maybe it's taking some of the motivation to crack-down and start jogging every morning (something I've already been setting an alarm to do, but just can't seem to force myself to do before work)

  • Since somebody's going to mention it, technically I'm doing all of "the boyfriend's work" without any of the pay-off. Plus, I'm further cementing myself as a "friend" as opposed to an "option". I don't really see it as that, because I feel like I'm gaining more out of this situation than she is, but I'm not going to pretend it isn't a factor.

  • Since I'm "validating" her, that also makes things easier for her current bf.

  • This is the one real curve-ball; a few weeks ago, she found out my birthday was coming up, and asked what I was doing. The answer was not much, so she took it upon herself to organize a "birthday party" and then do some bar-hopping. I've literally never had anyone (besides my mom or sister as a kid) "throw me a birthday bash", and that was honestly a nicer gesture than... well, pretty much anyone has ever done for me. So that's kind of dangerous.

  • I'm not sure what her social network looks like, but so far it's just been the two of us (save for the aforementioned party). So I may be losing out on some of the benefit of "being pre-vetted by another woman" if we aren't actually meeting up with any of her single friends. This probably just reaffirms the idea that she wants to hang out as validation for her.

So I guess I'm just trying to assess the situation, and determine if this is a problem, or if this is something beneficial?

This by no means has stopped me from going out with other friends when the opportunity arises, and I'm certainly not hoping for anything else to come out of hanging out with her. In my mind, I just see it as an opportunity to get out and socialize when I otherwise wouldn't, and if it serves the purpose of her being "validated", then that's probably a mutually beneficial arrangement, right?

Or are there variables or caveats I might not be considering?