Community's Alison Brie Wanted John Oliver As Annie's Love Interest

Most sitcoms get messy with the shifting romantic relationships between the cast, and "Community" is no exception. The first season features Annie (Alison Brie) first having the hots for former high school quarterback Troy, before making out with sleazy ex-lawyer Jeff. Then Annie dates a hippie guy who's also Britta's ex-boyfriend, before making out again with Jeff in the season 1 finale, right after Britta tells Jeff she loves him.

It was a chaotic situation, but luckily, the season 2 premiere came along and settled things over smoothly. In just one Betty White-filled episode, the show stomped out any whiff of Jeff/Britta being a serious storyline, and poured some cold water over the many hints of an Annie/Jeff romance subplot. "I think you're gross now," Annie tells Jeff at the end, and the line is taken with relief by everyone in the room. 

With Annie and Jeff never truly getting together throughout the next five seasons, who did the show pair Annie off with instead? Well, nobody, really. Beyond the occasional hints of a potential Jeff/Annie relationship and the brief mention of her online boyfriend (who was actually just Abed catfishing her), Annie rarely seem interested in romance at all. But for Alison Brie, it was a different story. When asked in a 2010 interview who she thought should be Annie's next "romantic conquest," Brie had an easy answer: John Oliver, AKA Professor Duncan. "I think it'd be funny," Brie said. "Talk about taboo!"

"Last season, we did the psychology episode, and it was our fourth episode we ever shot, and he and I did this experiment where we stayed up all night," Brie continued. "There was this one scene where we were both wearing argyle, and I was like, 'It's a sign! They both like argyle! They should be together.'"

Unfortunately (or was it?), Annie and Professor Duncan were never an item, and it's easy to see why. For one thing, the age gap between Annie and Jeff was already a pretty big deal-breaker, and it would have been even worse with Duncan considering he's a teacher at the school. A 19-year-old dating a guy in his thirties is sketchy enough; a 19-year-old student dating her 30-something professor is much worse. 

Admittedly, Alison Brie was nearly a decade older than her character Annie, which makes the age gap a little easier for audiences to ignore, but there are plenty of other obstacles to keep in mind. The first was that John Oliver, busy with his work on "The Daily Show" and then "Last Week Tonight," was never able to be a regular cast member. The second is that Duncan is a bit of a creep; he spends most of the show thirsting over Britta, even though she's his patient/student, and the humor wrung from this only works because his behavior never works out for him. 

But while a relationship between Duncan and his student would be deeply inappropriate, for Brie, that's sort of the whole appeal: "[Annie] has that forbidden fruit thing going on," she explained, "So why not be super taboo about it and have her be hot for teacher? [Laughs]." The writers never followed through on Brie's idea, but hey, maybe there's still time in the upcoming movie.