The first that came to mind is this, and im pretty sure it's not it, but still
https://www.mangago.zone/read-manga/tale_of_the_yellow_dragon/
Oh yeah, also, as I'm still trying to remember, after their first life, I think the Man was a Business Man, and then he bump a girl, I think it's a high schooler or college student, and that's when the Man knew that the girl he bump was his first love in their first life, and timeskip, the man met again in somewhat a cafe? The man saw his love from the window outside and he ran inside to grab his lover's hand only to find out she's a guy
I'm actually looking a BL Manhwa(I think it's bl?), In their first lives, a man and a woman both fell in love in historical times, but they failed to get together, and then in their next lives, in modern times, the man met his woman from his past life and fell in love again, but failed again. In another next lives, this keeps on repeating actually; the man met his woman and fell in love, but failed again. Until the man found his woman, but this time she's a man in their current life! I'm not sure which place they met again, but I guess the man met his woman (now a man) in the cafe, where he was just sitting there, and the man came up to him.
I have been looking this Manhwa for like 2 years now, I just found this on TikTok but never got to bookmark nor liked it