Season 5: Episode 104: The Walk to the Door
Ray is mortified when he meets a girl whom he dated 25 years earlier and believes he treated with disrespect. Meeting Elizabeth again, Ray, wracked with guilt because he feels he didn't behave properly on their high school date, is determined to apologize. However, when he finds out the real reason Elizabeth went out with him that night long ago, he regrets ever bringing up the past. Meanwhile, Debra demands that Ray give her an example of something he regrets, but incredibly he can't come up with anything.