You've been trying to control the situation by dropping hints and manipulating, hoping that people will react the way you want them to and that you'll get your way without ever having to come out and ask for it.
Don't do this ever, but especially not if his last girlfriend is the person you're going rock climbing with Sunday.
No matter what his answer is, it's going to make things weird.
This goes for friends and partners who haven't dated, too, now that I think of it.
Set aside time for each of them and honor it — don't drag your lover along on girls' night out (not even if your lover is a lady; queer chicks are about this), and don't invite your friend to what was supposed to be a romantic dinner at home.4. Don't ask your man if you're prettier/smarter/better at Scrabble than his last girlfriend.
What I've noticed, though, is that every person I've heard espouse this worldview was straight.
This rule is almost never stated or enforced among queer communities.
I can count the degrees of hookup separation between my closest friends and myself, and usually come up with no more than two or three.
In fact, when we met, my now-partner was on a date with my best friend.
They dated casually for a few weeks before they split up and we got together, and three years later the same friend gave one of the readings at our wedding.
Whether you're gay, straight, bi, or not into labels, dating a friend's ex can absolutely be done without sacrificing your friendship — you just have to follow a few simple guidelines.1. It's common to assume that anything shared with you is by default shared with your partner as well; however, your friend might be much less comfortable speaking to you in confidence if she thought the details of her personal life were going to be relayed to someone who used to share her toothbrush.
You and your friend are not in competition, except when you're actually playing Scrabble. Trust that your dude is with you because he likes you and you're awesome, not because he's biding his time until your friend takes him back.