Season 1

Six years ago, Annie (Casey Wilson) and Jake (Ken Marino) bonded over their mutual love of nachos and they have been inseparable ever since. Now, after returning from a romantic two-week island vacation, Jake's all set to pop the question. Before he can ask, though, Annie lets loose on Jake for his inability to commit. She was expecting him to "put a ring on it" in paradise and now Jake's perfect proposal is ruined. Not wanting to spend the next 60 years talking about that mess of a proposal, Jake and Annie decide to hold off on the engagement until they can do it right. Yet if history tells us anything, it's when we really want things to go right that they all tend to go wrong. The only thing we know for sure is these two are destined to be together - whether they can get it together or not.