My Best Friend's Girl is currently streaming on Prime Video

My Best Friend's Girl (2008)100 minComedy, RomanceRating 57/100

Tank faces the ultimate test of friendship when his best friend Dustin hires him to take his ex-girlfriend Alexis out on a lousy date, in a plan to make her realise how great Dustin is. The problem is, Tank finds himself falling for her instead.

Cast: Dane Cook, Kate Hudson, Jason Biggs, Alec Baldwin, Lizzy Caplan, Diora Baird, Taran Killam

Director: Howard Deutch