The Drew Carey Show (1995)

S3E17 The Engagement

Oswald reveals his intention to cohabitate with Kate, igniting Drew's jealousy and leading to a heated confrontation with her. Oswald confronts Drew, suggesting he's still hung up on Kate and claiming that he and Kate share a deeper connection than Drew does with Nicki. To settle the score, the guys opt to challenge their relationships by incorporating questions from a compatibility quiz during their Valentine's Day double date.