6 Celebrities Who Dated Their Famous BFF’s Sibling

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In theory, it’d be great to be BFFs with a mega-celebrity. Like, Taylor Swift sometimes brings her hometown bestie, Abigail, as her date to red-carpet events. (That’s one of many reasons we all want to be best friends with Taylor.) Free concert tickets, hearing all the insider Hollywood gossip, closet-shopping through celebrity wardrobes… Yeah, sounds like a pretty good deal.

But hold up for a sec and consider this: What if your celeb BFF started dating one of your siblings? It’s bad enough to feel overshadowed by your siblings for normal reasons, but now you’d have to compete for your best friend’s attention all the time. Say goodbye to being her red-carpet backup date! And let’s not even talk about the weirdness if your BFF and your sibling have a messy breakup. Yikes. Check out these stars who put their friendships to the test when one dated the other’s sister or brother: