should i ask out the waitress i've talked to for two years on my route or just let it stay small talk

i (58M) drive long haul, same route through the panhandle every ten days or so for almost two years now. theres a diner outside amarillo i always stop at and theres a waitress there, Dana (44F), we always end up talking longer than i should be on break for. she got divorced last year, i know because she told me before she told most of her regulars, which felt like something. lately its more than coffee talk. she remembers my order, i remember her days off, we joke about the same stuff every time like its a running bit. last trip she said "you're gonna have to actually take me somewhere one of these days" and laughed it off but i couldnt tell if that was a real door opening or just something people say. problem is if i ask and its weird now i lose the one stop on this whole route i actually look forward to. and i'm gone 5 days out of 7, dont know how that works for anybody let alone someone i'd be asking to wait around on. amber says just go for it, my buddy Denny says dont mess up a good thing for a maybe. keep replaying it in my head on the long stretches with nothing else to look at...

#shouldi#relationships

anonymous ask · Aug 21, 2026 · 282 votes · 3 comments