So I'm in a bit of a pickle.
There's someone I have known for 15 years or so (though we've sometimes have not had contact for years). Always was fond of her to be honest but that was never said, never the time, I was never in the right headspace, etc... She settled back here 18-24 months or so ago to open a shop so I made a point of dropping by to chit chat sometimes. I didn't expect to ever see her on the regular so was a bit eager to spend some time.
We had a number of confusing interactions then, she was very nice and politely curious of my celibacy (I was off my long term relationship). She was in to try to go see some dance show in the week but basically dropped all communications hours later as I was sending her the info on the remaining tickets we could grab. Then it came up she was a bit unsettled by surprise drop-bys so I stopped doing that and apologized for any awkwardness she experienced.
I just started to see someone a few weeks before at that point but kept trying to engage as a friend because... Well she is and I like her regardless... through short messages every trimester or so but basically had no response whatsoever. I should point out that it's not just with me, as I said she's very elusive even with other mutual friends who know her a lot better than me.
Flash forward to this week, she responds to my New Year wishes and apologize for being late at that, says she had a busy year. I say I look forward to speaking about that at any occasion around a drink, maybe if she shows up at a mutual friend birthday party in a bar. Which she did (honestly expected her to be a no show). We chatted a bit about what was going on in her life, the struggles of overworked bougie urban celibates, being a bit burnt out and going home to Netflix instead of making the most of social and recreational activities available, my experience (or lack of, really) with online dating and that she wasn't really looking for anyone right now... Left together to walk her off to the nearest taxi station, she jumped in a cab, I reiterated that she could call me whenever she felt like going out and get her mind out of work and that was that.
I asked around to get some good restaurants recs in her neighbourhood, just in case, but it's not like I even know what to do with that. All suggestions I made in the past for a eat or a drink were lost to ether and for all I know I may not hear of her for several months to a year. Was thinking of maybe messaging one of the restaurants name, that I heard good things about it and she had an opinion, without an explicit invite ?
I don't even know why this bothers me so much, I feel we would be a terrible match with our echoing issues, but the heart has yadda yadda yadda.
TLDR : I'd just man up and be open if I ever had the possibility but just getting to see is insanely convoluted.
