When Your Friend's Ex Likes You...
In a city like New York, it's impossible to not cross paths with people. You're bound to go on a date with someone who has been out with one of your friends. It's definitely happened to me several times, usually with the same mutual friend involved. Especially in the dating app era, we are so much more accessible to each other that it's impossible not to go out with guys who have been out with someone you know.
Dating in your 30s is different than dating in your 20s. Five years ago I would have never gone out with a guy who my friend had ever expressed interest in, let alone had gone out with. I wasn't really dating for marriage so my mindset was different. In my 30s, I'm dating to find someone. I just recently encouraged a girlfriend of mine to date a guy who I had gone out with a few times last year. It didn't work out for us but that doesn't mean he should be off limits for everyone else I know (which includes a lot of women). He is a great guy and deserves to find an equally amazing woman, like my friend.
If you find yourself in this situation, see how the date goes and if he's someone that you like, be honest with your friend. It's better to wait until after hanging out with him at least once because you don't want to start up possible trouble with a friend unless you are positive he is worth it. If the date goes really well, then call your friend and just let her know that you connected with this guy and you'd like to see where things go. I'm sure she will understand.
If the relationship with the guy and your friend was more significant than a few dates, you're now entering more dangerous waters. Really consider if this is someone you could have a long term relationship with. Think about the relationship he had with your friend. Why did they break up? If the breakup was her choice then you're in a better situation. If he broke her heart, then you are at risk of losing a friend and things possibly not working out with him. Again, if you really think he could be the one, it might be worth taking this risk but be prepared for the consequences. Is this guy worth losing a friend? Worth losing multiple friends? There are many people we could potentially end up with so, if he isn't 100% worth it, then let it go.
Really evaluate if the connection with this guy is purely sexual or if there is something more. Don't jump into anything. If you decide to move forward, take it slow.