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.
(I'm going to use female pronouns for your friend, and male pronouns for your sweetie, for the sake of simplicity; however, every rule here applies no matter the genders of the participants.) Keep your friend's secrets.
Set the precedent that people who are awful to your friends are people who don't get to see you naked, and your life will be the better because of it.
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Likewise, don't grill your boyfriend on what went wrong or insist that he account for his behavior throughout the entire time they dated.
Besides, comparing yourself to anybody — even if you come out ahead — is going to lead to feeling crappy, because basing your self-esteem on where you stand relative to someone else is Not Healthy.
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 4. Don't ask your man if you're prettier/smarter/better at Scrabble than his last girlfriend.
Don't do this ever, but especially not if his last girlfriend is the person you're going rock climbing with Sunday.
They believe this is something everybody knows, that they're just following the rules.
What I've noticed, though, is that every person I've heard espouse this worldview was straight.