Mark and Thom are in the apartment waiting for Katie to come back from Chicago. Thom looks at the flight online and says that she should be home any minute. Mark regrets letting her go to Chicago with David, and for messing up when she left. Mark says that he just wants to know if she had sex with David. James bursts in the room asking if she is home yet. They say no and James says that's great because he wouldn't want to miss whatever stupid plan Mark and Thom have planned. Mark hears rustling at the door and rushes to get it thinking it might be Katie. Hope walks in and when she asks Mark what he was doing he covers it up by saying he was admiring the doorknob. Hope has groceries and says that everyone owes her. Mark says he has a coupon, but she tells him to go get the money. Katie walks in and Mark and Hope greet her. Thom asks if she brought gifts, but says that if she didn't it's ok. James asks her how the weekend was and she says fine. She turns to Hope and says it was good. Mark asks her if it was good or fine, and she says the same thing. She sets down a bag and says there are cupcakes in them.
Thom and James are sitting at a bar and Thom remarks that it is great the two of them can be friends and do stuff without Mark. James clearly doesn't think this way and asks if Mark is coming as Mark walks in. Mark says that he finally knows the perfect plan. He bought theater tickets for him and her and will take her to a play. Thom says that this goes against their plan of waiting. Mark reminds him that that planned failed when she left for Chicago, and that this time he will make sure things work. They will go as friends, and then he'll turn it into a date. Thom and James say that buying her tickets is a big deal, especially if Katie is dating David. Mark says that he knows, but he believes in his plan of downplaying the whole thing.
Katie and Hope walk in and Mark tells them to play along. He tries to invite Katie to the play, but Thom ruins the plan by saying that he will go. Mark tells Thom no, saying that he is busy that night. Thom remembers that he has ballroom dancing, and then hits on Hope again. Katie comes back to the bar and Mark asks if anybody else wants to go and both Katie and Hope say they will go, and obviously Mark picks Katie, but gives Hope a coupon for cat food as compensation.
The next night, Mark goes to Thom's place to see if his jacket is still there from when he moved out. Thom says that it is gone, since he sold a bag of his stuff to his crazy neighbor Alyssa. Mark gets Mark, but Thom tells him to forget about it. He asks if mark is ready in the event that he and Katie get intimate. Mark says yes, and Thom gives him a shaver for his "hair down there". Mark says no way. Alyssa barges in with a pillow. Mark asks for his jacket back, but Alyssa says no because she made it into a pillow, and then she gives it to him. Mark says that he has plans and opens the door for her to leave, and she quickly sings another one of her made up Mark songs.
At the theater, Mark goes up the counter to get a big cookie, and the guy says that it is $14, which Mark thinks it ridiculous. The cashier says that he has to work for an hour and a half to make that, so Mark takes it. At their office, Hope comes running up to Katie's desk with a loaf of bread and tells her to hide it. Hope is pulling a prank, and when Pedro (the guy who brought the bread) comes looking for it, he blames someone else for it.
Katie is putting on lipstick for the theater and Hope asks whys he is wearing it just to go out with Mark. Katie says that she always wear lipstick out, but Hope says that she chose a slutty color. She says it can't be for Mark, and Hope says that it isn't a date, especially because he basically invited Thom.
David walks up to Katie's desk to talk to her, and David asks hope to leave. Hope says that Katie is going to tell her what he says so she might as well stay, but he tells her to go work. David asks Katie is she has plans because he really needs her to come to a business dinner with him. Katie goes to consult Doris (her co-worker) about what she should do, and Hope interferes and the girls end up telling Doris everything that has happened. Doris says to take both of them as lovers and make sure they don't find out.
At the theater, Mark feels a tap on his shoulder and assumes it is Katie. It is Hope, who tells him that Katie is stuck at a business dinner, so she will see the play with him. In their seats, Mark tries to get information about the dinner out of Hope, but Hope just keeps telling him to be quiet. Mark gets to be too loud, and the attendants kick him and Hope out of the theater.
At the dinner, Katie and David are having a good time. David asks Katie to try some of his food. Mark walks to the window of the restaurant just as Katie is offering David some of her food. Thom and James are at the bar, having an awkward conversation. Mark walks in and tells them how the plan failed. Mark says that maybe he should give up on Katie. Two girls walk over and say that Mark looks sad, and maybe they can help. They then sit down.
At the restaurant Katie says that she doesn't think it is a good idea for them to take this romantic path, but David says that their attraction to each other already puts them on that path. Katie then tells him about how she kissed someone else and she doesn't know how that path is going to go, and she needs some time to figure it out. David says that sounds good, but when Katie asks how long he is willingly to wait, he says midnight.
Katie goes back to the apartment. As soon as she walks in Hope says they need to talk. Hope tells her that Mark paid $300 for the tickets, and didn't get them for free. She says that Mark must have been downplaying the night because he didn't want it to seem like a date at first. Katie says that Mark didn't make a move before she went to Chicago. Hope says that he must be trying to cover up his true feelings for her. After realizing that he could have easily hung out with her for free, they realize Mark must be up to something. They decide to go to the bar and talk to him.
At the bar Mark and Kelly are having a good time. They kiss the moment that Katie and Hope walk in and Katie says that he has a funny way of showing that he likes her.
Another day at work, Katie asks Hope if she wants to go out to lunch, but Hope says that she is going to eat in. Katie leaves and Hope gets ready to eat. She gets a call and has to do something. After she leaves the room Pedro comes to her desk and steals her lunch. She comes back, and immediately knows it is Pedro who stole it.