Season 4, Episode 16: "The Shoes"

You are never gonna believe who I just ran into today.

-Who? -Your old flame: Gail Cunningham.

Did you talk to her?

Well, I was on my way to the Y, and I saw her coming towards me.

I didn't know what to do.

I remember you had three dates with her...

...and she wouldn't kiss you good night.

So now I'm thinking, "What is my duty to my friend?