Lewis, Oswald, Drew and Steve are sitting down on Drew's couch, playing Pictionary. They're trying to get his mind off of the break-up with Kate. Drew walks out of the room and comes back with a butternut squash, and starts to cry because Kate gave it to him.
They suggest to Drew that he get a new girlfriend, and then Mr. Wick comes in with a big harp. Drew thinks it's a little "gay" and doesn't like it.
At the Warsaw, Lewis and Oswald are talking about spending money on infomercial crap. Oswald does a magic trick to try and impress a woman, but it doesn't go so well. Kate comes in to order breakfast, at 8 PM. She's depressed about the breakup, like Drew.
Kate finds out from Lewis and Oswald about the plan for Drew to sleep with another woman to get over the break-up. Kate runs out to stop him.
At home, Drew is sitting on the couch while Mr. Wick plays the harp. They both start to sing a song, "Windy." Then Steve walks in, and joins them in song.
Drew is searching the personals for single people. Steve says he's made a date for him, and she's going to meet them for a drink in a few minutes.
Kate walks in after Drew and Steve leave. Kate is sad and depressed again, and Mr. Wick sees an opportunity to score.
At the restaurant, Drew and Steve meet up with Drew's date, Jenny. Mimi walks in and Drew finds out that Jenny is Mimi's cousin.
After the dinner discussion goes bad, Steve and Mimi leave. Jenny starts to flirt with Drew and, well, it turns out Drew's date isn't wearing any underwear.
At Drew's house, Kate and Mr. Wick are talking and getting drunk. Kate's still sad about Drew. Kate comes up with the idea of sleeping with a guy to get over Drew. Instead of leaving, she takes Mr. Wick upstairs.
As they're going upstairs, in walk Drew and Jenny. Drew and Jenny walk into a bedroom and start fooling around. After Jenny starts talking a little about her and Mimi, Drew leaves to get some protection.
In the other room, Kate changes her mind about sleeping with Mr. Wick. He tries to get her to change her mind. As Kate is leaving, she runs into Drew. Drew wants to know what she's doing with Mr. Wick in the other room. Drew and Kate get into an argument, and they go back to their rooms.
Drew starts hitting the wall with his elbow to make her jealous. Meanwhile, Kate is just sitting in the other room, and Drew bursts in to stop her from having sex with Mr. Wick.
Drew and Kate start talking about things and make up.
Jenny, who wants some sex, ends up with Mr. Wick that night. It all kind of makes sense.
Drew and Kate decide to go back to being friends. Drew goes to ask Kate if they're the kind of friends with benefits, but she says "no" before he can finish his question.
The episode ends with some bloopers.