Katy Perry & John Mayer

What Actually Happened: The night before the 2009 MTV VMAs, Katy Perry and John Mayer met for a drink at a bar in NYC, after weeks of exchanging flirty emails and texts. "John thought she was so hot and fun and was into her," an insider told E! Online at the time -- and Katy was equally into him. The next night, however, at the VMAs, another dude caught Katy's eye -- Russell Brand -- and he was quick to pursue. We all know what happened next -- a whirlwind romance, engagement, marriage, divorce -- with Mayer left in the dust.

What Could Have Happened If They Became A Couple: Well, Perry certainly wouldn't be a divorced woman, Taylor Swift would have never had her heart broken by Mayer's player ways, and he wouldn't be moaning and groaning to Rolling Stone about how "lousy" it made him feel. While they would be total tabloid fixtures, I don't think their love story would be as interesting as the one between Katy and Brand. And regardless, I would continue to be completely grossed out by John Mayer.

Level Of Relief This Couple Was Not Meant To Be: Non-existant. Couldn't care less if they did or did not work out.