You and your best friend share lots of secrets and have lots in common, but an ex shouldn't be one of them. I don't advise dating your best friend's ex unless it's been a long, long time, and even then, I guarantee your friend is going to feel you're being disloyal.
The Everly Brothers had a song about bird dogging (which is dating your friend's date), and the song, not the concept, was a big hit. I know it makes some kind of logical sense. After all, you and your friend do share a similar sense of humor, a fondness for James Bond flicks, and a willingness to cover for each other when necessary, but sharing a love interest, even serially, only works in Hollywood movies, and even Hollywood admits it can get pretty sticky.
You don't have to believe me. Just think about how you'd feel if your best friend started dating one of your exes. Are they talking about you? Comparing notes? What if you come in second? If nothing else, if your friend starts dating your ex, you'll either end up saying, "See, I told you so" or feeling that your friend has something you don't . . . like your ex.
If you're bound and determined to date your friend's ex:
1 Wait at least a year or so after the break-up. Any earlier, you're talking rebound: You'll lose a date, a friend, and your mind.
1 Don't ask permission. The first date can be kept quiet (after all, who knows how things will go?), but if it seems to have some potential, tell, don't ask. Just explain that you bumped into one another and plan to go out for coffee (you can finesse that first date), but keep the details to yourself whether it's going very well or very badly.
1 Ask yourself, "Is it worth the friendship?" That will very likely be the cost.
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