5. Chip Matthews (Dan Gauthier) – THEN

Chip is that guy at school that we all look back on and hate: arrogant, a bit of a bully, and a major player when it comes to girls. So it figures that both Rachel and Monica fell hard for him in their youth – We’ve all fallen for the bad boy once in a while! But since Monica never got the chance to date him, when he turned up in her life again, she decided to give it a shot.

And booooy, was she in for a shock. Turns out he still lived with his parents, worked in the same place, hung out with his old school friends, and even gave wedgies. Wow. It doesn’t take a genius to understand why this particular ship didn’t sail. Monica explained it all: “You know how I always wanted to go out with Chip Matthews in high school? Well tonight I actually went out with Chip Matthews in high school.”

So what’s the face behind Chip been up to since then? Well, thankfully he’s got up to a lot more! He’s appeared in Supernatural, Criminal Minds, Faking It, and One Life to Live. He’s even been nominated for two awards!

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Dan Gauthier (Chip Matthews) – NOW

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