In the Season 2 episode " Breaking Up Is Hard to Do " from A Different World , multiple characters navigate romantic complications around Valentine's Day, including Dwayne's failed proposal, Jaleesa's prank backfiring, and Kim's discovery of her boyfriend's infidelity. You can watch this episode on IMDb or read about it on the Different World Wiki .
"A Different World" Breaking Up Is Hard to Do (TV Episode 1989) [S2E14] Breaking Up Is Hard to Do