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.
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That's certainly the case when you find yourself attracted to your ex's friend!
Depending on the situation, it might either be a funny coincidence or something that could tear apart a friend group. Is the guy you're into your ex's best friend, or are they just friendly acquaintances? (Seriously, don't do that.) All these factors will help you decide if you should act on your feelings.
This goes for friends and partners who haven't dated, too, now that I think of it. Don't ask your man if you're prettier/smarter/better at Scrabble than his last girlfriend.
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. Don't do this ever, but especially not if his last girlfriend is the person you're going rock climbing with Sunday.
It's difficult to meet people you're romantically interested in beyond an already-defined circle, and outside of your city's queer scene, most people you run into are likely to be straight.