My latest conundrum: My mom's dentist's receptionist is this gorgeous Brazilian girl, probably about 24-26 (so well over a decade my junior, not that it matters much 'cause everybody thinks I'm 28-30ish anyway until they find out otherwise).
We had such a good rapport the two times I ever met her / talked to her that after the first time my mom was commenting on all the body language cues the girl was giving me, like leaning over the desk towards me with her boobs squeezed together, and giving me "twinkly eyes" and smiling when we were having eye contact, stuff like that. My mom was like "she looked like she wanted to eat you" and she never says stuff like that about girls, so it was that obvious. She also didn't treat any other guys like this while we were there.
I've built relationships off of less than that on a first interaction. Second interaction was a little less flirty but still nice and she said it'd impress her if I came in next time knowing some phrases in Portuguese. So I went and learned a few, like "how's it going", "you look great", and "I don't know how to say anything else"
I'll see her again some time soon when my mom does the follow-up (which should be in the next week and a half or so) and I'd like to ask this chick what she's up to for Valentine's Day and maybe see if I can slide in and take her out.
Where's the conundrum, you ask? The conundrum is that I suck right now. I'm not in shape (after being in very good shape for like two decades, I've slid a lot in 2023 from overall depression). I still look good, but I'm not healthy, I'm low energy, I'm injury prone, I'm not someone I'd want to be with and I don't want to waste anybody's time. So my confidence level sucks now and certainly isn't at the level it needs to be to confidently address someone this gorgeous. I'm concerned I'll come off un-confidently or bungle my words or scare her off or any number of things. And of course the more I roll this around in my head, the more nervous I get and the less I even want to deal with it. Also feels like when my age comes up it's always a Thing with women in their 20's. Which is all I want to date, so...
Haven't cold asked anyone out in-person in a couple years without some sort of online communication first, so a lot of my approaching skills have atrophied. I can say that it definitely feels like I'd be jumping the gun if I asked her out now, but if I have another good conversation with her and the rapport is there, I could definitely ask at the end of that next conversation.
Not sure why I'm even writing all this stuff. I'll either do it or not do it, she'll either say yes or she's in a relationship already and inexplicably flirtatious with only me.
