What does a guy mean when he always says "You win" all the time?

[Anonymous]

This guy and I had a thing a while back. He transferred to another town, and he got a girlfriend. Whenever he would talk to me, he kept flirting with me by the way, he would always say "she wins", he moved back, they broke up, and now he's been messaging me a lot, teasing me, flirting, and he keeps on saying "I win" now...?

He also keeps on making plans for us to do stuff together...?

[udolipixie]

Why'd you ask this question if you already have an answer you want to hear.?

"He means you win his heart. He wants to be your bf"

Why not ask him to get the answer instead of asking this to get the answer you want?

Though I don't know why'd you would want a guy who flirts behind his gf's back and considers himself such a prize he must be won.

[Maxstrosity]

Don't mean to be Harsh but this guy sounds like a real winner. As udolipixie put it, do you really want to be with a dude that flirts behind his GF's back? He will probably treat you the same.