20 Weirdest Celeb Couples – You May Be Surprised

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19) Jennifer Aniston & Adam Duritz

For a single week in the mid nineties (1995), the singer from Counting Crows dated Friends star Aniston. He subsequently admitted that perhaps this wasn’t all it was cracked up to be. In a 2009 interview with the Sunday Herald, Duritz said “Some people you really dream about dating. Then, when you get there, you think, ‘Wow, this is not the vacation I thought it would be. This is not where I want to spend my vacation.” People, after all, will always be people (rather than glamorous movie stars in every aspect of life).

Duritz isn’t the only one to find Aniston a high maintenance girlfriend. She’s been through a string of men (including John Mayer, Vince Vaughn, and Brad Pitt). Duritz, on the other hand, immediately coupled up with Aniston’s BFF Courtney Cox. This would generally be a big burn to the girl code, but Duritz claims that he and Aniston never even slept together. Duritz and Cox were an item for some time which led to a split between her and Aniston, but they seem to have since patched things up.