Designing Women (1986)

S2E11 Howard the Date

In a disastrous act of kindness, the Sugarbakers team takes dateless Howard, the nerd, to his high-school reunion. Initially motivated by sympathy, their patience rapidly diminishes as Howard brags about his romantic exploits with "four women." His overconfidence turns the outing into a cringe-worthy experience, leaving the staff questioning their decision to help him.