How I Met Your Mother: Ranking All Of Ted Mosby’s Serious Relationships From Worst To Best

5. Karen (Played By Laura Prepon)

As his college sweetheart, Karen was the first woman that had Ted wrapped around her finger. Karen perfectly embodied a snooty college student who ridiculed others for their lack of sophistication, suggested classic literature for others to read, and corrected restaurants whose wine menu’s had Chateauneuf Du Pape listed under Côte De Provence.

While at Wesleyan University, Ted was an equally insufferable know-it-all. They attended separate college’s, but Karen and Ted managed to stay together, much to the chagrin of Marshall and Lily. Despite how well they got along, there was a clear disparity when it came to interest levels in their relationship. Karen would habitually cheat on Ted which, when caught, would leave him heartbroken and devastated. Ted would always head to Karen’s college to confront her and, rather than stand his ground, the two of them would get back together and the whole cycle would start over again.

Despite their disfunction, the duo briefly rekindled their romance later in life, despite much protesting from Ted’s friends. Even when Ted found out that Karen was cheating on someone else with him, it wasn’t until she presented Ted with the ultimatum of choosing between her or his friends that he ended their relationship.

Karen represented everything Ted thought he wanted in a girlfriend during his late adolescence. Ted and Karen exemplified how difficult long distance relationships can be, especially in college, and while Karen was an entertaining character, we can be thankful that she didn’t pass Lily’s Front Porch Test.