Friends: Rachel's Boyfriends Ranked!

The fascinating thing about Chip Matthews is that he never actually dated Rachel during the course of the show. Instead, he was her childhood sweetheart, although maybe not so sweet and certainly not a good boyfriend. You never actually saw the pair together during their adult lives, but what you learned about their past certainly makes him worthy of a low ranking here.

Chip and Rachel dated during high school, but he broke up with her to get with someone else. After getting back together (it seems Rachel has a thing for on and off boyfriends), they went to prom, where he turned up late and left with another girl.

You meet him in the show when he goes on a date with Monica and learns that he's exactly the same as in high school. Thus, Chip is unlikeable, immature and was a terrible partner for Rachel.

He was an all-around tool and only manages to overtake the previous characters because Rachel at least dated him for some time, even if it was terrible.