Not dating my best friend
We know our backstories will be tangled and intertwined.
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.
No matter what his answer is, it's going to make things weird.
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.
You and your friend are not in competition, except when you're actually playing Scrabble.5. Don't try to keep your boyfriend and your bud from associating because you're afraid they still have feelings for each other, and don't constantly seek reassurance that that's not the case.
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.