If he’s been rebuffed by you for many years, he probably doesn’t expect you to be interested in dating him, any more. If you’re now truly interested in dating him, you need to let him know by saying something like, “If you weren’t in a relationship, I’d be ready to go out with you, now!” He then has a clue that you’re ready, if he is.
If he breaks up with his girlfriend to date you, that’s one way he can show you he’s really interested in having a serious relationship with you. If he wants to cheat on his girlfriend with you, then you’ll know that that’s what he’s got in mind. But it sounds like it’s up to you to give him a clue that you’re not going to turn him away again after all these years if he comes up with a genuine offer that works for you. 😉
Let me know how things go, and please follow me @AskAprilcom on Twitter and on Facebook at this link: [url][/url].