The guy took Rory’s virginity while he was newly wed to another woman…and the insecurities-riddled relationship only went downhill from there.
Rory’s (and everyone’s) initial impression of Logan was that he was a douche-y rich guy…and whad’ya know—over the course of a couple of seasons, he proved himself to be a douche-y rich guy (albeit one who had mastered the art of the grand gesture).
Yeah, we know Jess was kind of a deadbeat. But damn if he didn’t have the bad-boy thing down pat.
1. Teenage Dean
Curse you, seasons four and five Dean, for ruining our previously unmarred infatuation with season one Dean. He built a car for Rory and said “I love you”! Knees…getting…weak. Sixteen-year-old Dean is all of our first loves, but with a bowl haircut that actually looked good.
4. Jason (a.k.a. “Digger”)
We knew Jason was bad news when he couldn’t take no for an answer from Lorelai. But he just had to keep pursuing her…only to decide to sue her dad after they got together and things started getting serious. Points for having a sweet pad, though.
The first time homeboy proposed, he said, “We should get married,” in the middle of a fight with Lorelai. The second time, he did it over the phone. The 1,000 yellow daisies were a nice touch, but seriously, dude?
We gotta say, pre-series neglectfulness aside, Christopher pretty much always tried to do the right thing for Rory and Lorelai (minus the whole drunkenly lashing out at Luke thing in season five). How could you not feel bad for him when Lorelai ended their short marriage because she realized she still wasn’t over Luke?
Okay, no surprises here. You just can’t beat seven seasons’ worth of sexual tension. We can’t wait to see what these lovebirds are up to in the revival (for the love of god, Netflix, you’d better not mess with this match made in Stars Hollow heaven).