Even at a young age, Jon Hamm had a certain je ne sais quoi.
It turns out that Rudd once competed with the dreamy actor for Clarke's affection.
So here's how it went down…
Rudd was a freshman at the University of Kansas when his roommate, Preston Clarke (You guessed it, Sarah's older brother.), invited him to stay with his family in St. Louis.
During Paul's weekend stay, the actress-to-be invited over her senior prom date, a certain Jon Hamm, to introduce him around.
And things only went downhill from there, according to Rudd…
"He seemed like he was a good-looking, athletic guy who possessed qualities I did not possess," Rudd recalled.
"We were playing Trivial Pursuit in teams. Sarah and I were on one team, and Jon and Preston were on the other team. Jon would want to go right to Yellow, which was History, and I was like, 'Oh great, this guy is smart, too."
Brains and beauty are an unbeatable package. Sorry, Hamm, we had to.
But things didn't end up playing out for Jon and Sarah.
In fact, she began dating Rudd shortly before he moved to Hollywood!
And after seeing his one-time romantic rival in the cult classic Clueless, Hamm decided to take a leap of faith and move to Hollywood in the hopes of launching his career in the biz.
It's a happy ending all around, too, as Jon and Paul remain good friends to this day.