So, last year I met an older (female) coworker's daughter at a company event. I don't work directly with the mother, but in the same office. Mother is still attractive despite her age, and the daughter is straight smoking.

When we met last year, it had been an open bar, so we were joking and had kind of a playful banter going. I failed to really make a move, though, and as she (and the mother) had left, she'd told me I was "pretty cute", and hoped to run into me again.

Welp, it just never happened.

Until just fucking now.

I was just returning from the restroom when I happened to see her (and several others) in the office across from me. I thought I'd recognized her, but was just like, I guess I'll get back to work. I couldn't tell if it was her or the mother who called out to me, but I sort of doubled-back, and as a bit flustered. I said hey, asked how she was, then someone asked her something (she was clearly already in a conversation).

Anyways, a couple minutes later (after I legit finished something work-related), I went back and said "Sorry bout that, was just in the middle of something earlier. What brings you this way?".

For some reason, it just felt super forced. Admittedly, I over-analyze myself, and I'm really not someone with any idea how to flirt or really even make meaningful banter (at least, definitely not sober).

I don't know why, but the brief exchange just really makes me feel like a loser with no 'game'. Like... could I really not think of anything more interesting to say than "How've you been?" or "What brings you this way?"? Could I not have found some way to try and ask for a number?