I [M] helped my friend’s G[F] move on

This happened around 8-9 years ago, and is one of those experiences you don’t easily forget. Back then I had this friend called Dan, which at the time was one my best
friends. We were always doing stuff together, either with all of our friends, just the two of us, or together with his girlfriend at the time, called Lana. The main reason
we were so close was actually because he was pushing it. Always calling me to hang out, coming by, “accidentally” bumping into me at places he knew I would be. Despite being
very annoying at times, he was a relatively OK guy, and we did have fun together most of the time, so I let all of those things slide. When we met, he had just broken up
with his girlfriend of 5 years and was in one those awful states where he would just go on and on about women and how much he was hurting. But being the nice guy that I am,
I endured.