The roommates are at a bar, and James sees a hot girl that he wants to ask out. However, she has a less attractive friend, so he needs Mark to distract her since her friend is going to try and get rid of James. However, Mark won't help. The girls are playing darts, and Katie says that it is Mark's turn. She tells Mark that he needs to win so she can keep her money. Hope asks Katie is the trip her boss asked her to go on is really a business trip, or a getting down trip. Katie says that she won't know until she goes, and she says that she will tell Hope every detail. This upsets Mark, and his dart misses and knocks a bunch of stuff off of a nearby shelf. Katie says that she wants a rematch with Hope, and to make sure it is something Mark is good at. James goes back and says that he got the girl's phone number, and mark remarks how fast he was.
Katie and Mark are in the living room. Mark is watching TV and Katie is counting money. She asks where James is because he needs to kick in some money for game night. Mark says that he hasn't seen him since he left the bar with a girl last night. Then James walks and brags about how well it went. Katie says that he needs to chip in $10 for game night, but when he goes to get his wallet, he realizes that it is gone. He realizes that the girl stole it in a classic one night stand move, and says that he was too sloppy in his work.
Katie says that they need to win on game night and asks Mark what games he is good at and he says Twister, cartwheels, and pretending to make out. Hope comes out and jokes about him, and then says she has the perfect blouse for Katie to where in Chicago, saying that it comes right off. Katie says that she is not sure her boss even likes her in that way, but Hope says he clearly does. Hope and Katie go to try the top on and Katie says that she wants Mark's opinion too, and he says that he likes the top, and her bottom, then quickly correcting himself saying her pants not her butt.
They go into Hope's room to try the top on and Hope tells Katie how to act to make David want her, and Mark gives his own advice. Katie tells Mark to shut the door so she can try the top on. Mark sees Katie with just her bra on and feels awkward, and then James bursts in. He says that he can't get a hold of his date and if she calls let him know. Katie tells James to get out of the room because she is changing. James gets a good look at her before Mark forces him out.
Mark tries to leave, but Katie says he can't and then asks what he thinks about the top. He then strangely says that she looks hot and sexy and she is happy. Mark goes to Thom's and tells him about Katie changing. Thom is happy saying that he is 11 months ahead of schedule. Mark asks what he is talking about and Thom says that if Mark doesn't get with Katie by October 2014 then he is giving up on him and worrying about himself. Thom says that he needs to make Katie see him (Mark) as a sexual being, but he doesn't know how.
There is a knock on the door and Thom goes to the door and looks out the peephole. He sees that it is Alyssa. Mark doesn't want to see her, especially now. Thom tells Mark about how crazy she has gotten since he moved out. Alyssa just opens the door and apologizes, but stays anyway and starts talking to Mark. She tries to make conversation but Mark avoids it. She says that she needs to go write another song about him and then leaves.
At game night, the roommates are playing a guessing game, and once again Hope and James beat Mark and Katie big time, 15 to 5. Suddenly Thom walks in and as Mark greets him, Alyssa walks in and goes straight to Mark and start hugging him. Katie then gives Hope a curious look. He introduces Alyssa to everyone. James decides to have some fun and tells Alyssa that Mark talks about her all the time. Mark then shoots James a dirty look.
Mark drags Thom into the kitchen and asks why he would bring Alyssa over, and Thom says that she will make Katie jealous. Alyssa brings them back into the room and says that Mark is no her teammate, and when he tries to go back to Katie, Katie says she'll take Thom.
Someone knocks on the door and James goes to get it. Katie and Hope ask what Alyssa does for a living, and they find it to be very strange. James comes back with an envelope in one hand and his wallet in the other. He finds it strange that his date sent it back, and Hope says that obviously she doesn't want to see James again. James says there must be another reason, but everyone moves on and goes back to the game.
The first round is Hope and James, and James is too upset about the girl dumping him, and they lose the round. Mark and Alyssa go next and Alyssa guesses all of the people correctly, and Mark gives her a high five, which she loves. Everyone is surprised at how good Mark is all of a sudden, and Alyssa says it is because of a special connection.
Later the night, everyone is clearly drunk and no one knows who is winning and losing. Katie goes into the kitchen to get a snack. Mark follows and in there Katie is admiring an apple. Mark apologizes for being a bad teammate earlier, but Katie says it is ok and then she kisses him just as Hope walks by.
The next morning Mark is cooking breakfast and James walks in. Mark tells him that Katie kissed him. James says that now he is going to need booby lessons. He asks what happened after the kiss, and Mark says they went to bed. James criticizes Mark. Katie walks in saying that she needs coffee. Mark tries to bring up what happened the previous night, even going as far to make Katie breakfast. However, Katie doesn't remember the kiss, and soon leaves that table.
She runs into Hope's room and wakes Hope up. Hope thanks her since she was having a nightmare. Katie says that Mark is acting weird and asks if anything weird happened. Hope says that Katie kissed him and she was all up on him, leaving her horrified.
Mark rushes over to Thom's apartment and tells him that Katie kissed him. Thom says that his plan worked and that now all Mark has to do is wait for Katie to remember and then things will be smooth sailing. Mark thanks Thom and goes to leave. However, Alyssa is at the door.
At a bar, James is panicking wondering where Heather, his one night stand is. Hope is glad that a girl is finally treating James the way he treats girls. Katie asks why he wants her, and James says that he wants her to want him more then he wants her.
James goes to talk to her and Hope asks Katie about Chicago. Katie is not sure about whether or not she could having a sexual relationship with David, or if her kissing Mark means that she likes him. Hope reminds Katie that when she moved in she thought James was hot. She says that she should sleep with Mark and see how she feels the next morning. She gets serious and says that if Mark likes her he will make a move before she goes to Chicago. James is still talking to Heather and she says that she doesn't want to commit and their relationship is over, leaving James bitter.
At the apartment, mark is sitting on the coach when Katie comes out, ready to leave for Chicago. She talks to Mark saying that word on the street is that they kissed, but they quickly move into an awkward conversation about how windy and cold Chicago is.
Katie goes to leave but Mark calls her name and he loses his cool and says something awkward instead. He opens the door for her. They try to hug, but with the awkwardness, they just shake hands and then Katie leaves.
At a bar, Thom and Mark are encouraging James to get over Heather. He tries to ask a girl out, but ends up acting like Mark and she leaves. He goes up to four other girls, but they also leave. Thom then tells him "welcome to the club".