Roger Dodger & Donnie Darko

Campbell Scott and Jennifer Beals as Roger Swanson and Sophie in "Roger Dodger" (2002).

"Roger (Campbell Scott) is a fast-talking lothario with the usual laundry list of the insecurities, sexual or otherwise, that plague the modern man".
Jesse Eisenberg as Nick in "Roger Dodger" (2002).

"Roger's sixteen-year-old nephew Nick (Jesse Eisenberg) appears for a few lessons on the art of pitching woo. In three brilliantly scripted and wondrously paced sequences, Kidd points his Casanova Virgil and virginal Dante into the concentric circles of casual sex hell: the Happy Hour pick-up, the drunken party encounter, the brothel-bound hooker. A nigh brilliant stream-of-male-consciousness black comedy filmed with genuine flair and theory by first-time hyphenate Dylan Kidd, Roger Dodger is a film with Labute-ian teeth minus the accompanying misanthropy. It hits its marks with a feline sure-footedness, eliciting career performances from Scott, Jennifer Beals, Elizabeth Berkley, and young Eisenberg who, mark my words, will be a star.
Jake Gyllenhaal as Donnie in "Donnie Darko" (2001).

As satisfying and accomplished a debut since Richard Kelly's Donnie Darko, Kidd represents another in a new wave of Hollywood film brats with the chops and love to rejuvenate an American industry that has fallen into disrepute: they are the true successors to Zoetrope's romantic promise, and Kidd has a lot to live up to with his sophomore feature"

"Nick arrives in New York as the randiest boy from American Pie, begging his dissolute uncle for help in losing his virginity that very night, but he abruptly becomes all Jake Gyllenhaal-sensitive. The gag, for lack of a better word, is that Nick's being sincere and open works far better with the ladies than Roger's slick, generic pick-up lines and coarse leers". Source: