Only one true way to figure it out.
Did the break up end badly?
If they hate each other, don't under any circumstances get with that chick, because you're buddy will have to be around some chick he can't stand and he won't want to hang out with you and your new girl. Then you're gonna have to make a difficult decision regarding the order of "Bros" and "Hoes".
If their breakup went well and they still get along and hang out with the same crowd, then have at 'er. If he can be around her and he says it's cool (you've gotta believe him), then it souldn't be a problem.
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