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Former porn star Gruber is 20, and famed fashion designer Klein is 67. These two, who began dating when Wood was 19 and Manson was 38, wanted us to think they're freaks throughout their years-long on-and-off relationship.
As with many of these couples, we understand why they exist (in both gay and straight forms! And you know us, we always give celebrities what they want. Swift is obviously preternaturally bright and motivated, and they're both tall and gorgeous. But don't make us pretend there's nothing strange about it!
While they dated, Valderrama was 20 and Moore was 16. Of course, the icing on the proverbial cake came when he went on Howard Stern later and bragged that he'd taken Moore's virginity. "But it wasn't like warm apple pie." No wonder that guy is always making a face like someone just punched him between the eyes.
Miley may be willfully sexy now, but back when she was 16 she was battling controversy over that vaguely sultry Annie Leibovitz photo in Vanity Fair.
Has the new year already brought out the first celebrity odd couple of 2010?
On New Year’s day, “Heroes” star Hayden Panettiere was spotted getting cozy poolside in Miami with Ukranian boxing champ Wladimir Klitschko.
To be fair, it's not like anybody is saying this particular pairing is completely normal.
That's when she started dating co-star Brian Austin Green, who at the time was 30.
Don't worry, Fox was alive when David Silver watched Scott Scanlon shoot himself in season one of Beverly Hills, 90210.
She was also smooching male underwear model Justin Gaston, who was 20 years old.
Said Miley's dad, Billy Ray: "He actually reminds me a lot of myself when I was 20 years old." Aw. You're used to this kooky couple by now, but before Megan Fox was the full-grown sexy Shakespearean that she is now, she was an 18-year-old star of the Kelly Ripa vehicle Hope and Faith.