Whether they were actually a thing or just friends, a countdown to the most devastating two-somes that didn’t make it in Tree Hill.
Dan & Rachel
This relationship was as short lived as Rachel’s stripping career. Even though she was totally milking him for his new found fame and fortune with Scott Free Redemption, she took it too far by forcing him to film an episode where Jimmy Edwards kills himself. Bad move, Rachel.
CW
Karen & Larry Sawyer
Karen and Larry first bonded as chaperones for a Ravens away game in Season 1. The two share a couple of brews, sneak onto the football field to uncover an old time capsule, and bond over being single parents. Although Larry tried, I think this relationship was more of a friendship and would best work platonically. (Plus, just imagine the awkwardness of Lucas and Peyton… gross)
CW
Grubbs & Miranda
In case you don't remember, Grubbs was the bearded guru bartender who replaced Chase at Tric, and he started an album at Red Bedroom Records with Miranda (Haley’s awful British assistant). Once Grubbs began producing his album about love lost, Miranda actually started to fall for him. But in true ice queen fashion, she turned down his proposal with her Visa about to expire.
CW
Dan & Karen
High school sweethearts always make for a wonderful story. Some play out like a fairy tale: boy meets girl, boy/girl fall in love, get married, have a baby, and live happily ever after. For Karen, news of pregnancy came before marriage (and college), leading to the end of her romantic relationship with Dan (and the fact that he got another girl pregnant and decided to marry her instead could have had a little bit to do with it too). Fortunately for Karen, she totally lucked out raising Lucas on her own (as seen in the episode “What If" in Season 2 after Nathan’s Nascar accident). Although they start to rekindle the flames, once news of her pregnancy breaks, we all know which Scott is really in her heart.
CW
