The moment I watched the Community D&D episode, IT Crowd immediately came to mind.
In this episode, Roy is going through an ugly breakup. He has problems moving on. Moss then pretends to be an elvish version of Roy's ex-girlfriend. It gets awkward at first, but eventually Roy gives in. Shhhh...don't fight it. sorry. *cough*
IT Crowd is one of my favorite shows. I highly recommend this show to those who are always up for a good laugh