A Lot Like Love (2005)

Synopsis
Two friends who've convinced themselves they would never make a good couple discover they might just be wrong in this romantic comedy. Oliver (Ashton Kutcher) and Emily (Amanda Peet) first met when they were college students sharing a flight from California to New York; Emily spontaneously seduced Oliver on the plane, and they spent the next few days together in the city. When they parted, however, Emily decided not to pursue a relationship with Oliver, even though he was obviously interested. Over the next several years, circumstances kept putting them in one another's paths, and over the years Oliver and Emily became close friends and confidantes. Both are still certain, though, that they're entirely wrong for each other on a romantic level. However, after nearly a decade, with both Oliver and Emily edging into their thirties, they begin to wonder if they've allowed a great opportunity to pass them by. A Lot Like Love also stars Kathryn Hahn, Ali Larter, and Kal Penn. ~ Mark Deming, All Movie Guide