After a few warnings from Robina and Matthew, Leah catches her boyfriend cheating on her. Unable to find her best friend, Robina, she asks help from Matthew. He offers to take her home, but once they get to her house, she says she doesn't want to be alone (her family's out) and asks him to stay. Matt thinks it's inappropriate to be in a house alone with her, so he offers to let her stay at his place, where he is staying with his brother and sister-in-law.

In the middle of the night, Matt wakes up to find that Leah can't sleep. He goes over to her, and tries to comfort her. In the heat of the moment, they almost kiss, but Matt stops them. He says that he doesn't want to take advantage of her vulnerability, and Leah agrees. She thanks him, and goes to bed.

Once Leah finally falls asleep, Matt realizes that he really wishes that it wasn't her vulnerability that made her want to kiss him.

Matt finally gets the courage to ask Leah out. At first, Leah thinks that he's only saying it to try and cheer her up. Later on, she realizes that he was actually asking her because he might like her, and not because of pity. She finds him, and says that she, too, thinks that the two of them might work.. and yes, she'll go on that date.

Matt and Leah go on their first date. Sadly, Matt doesn't know how to really plan a date, and a lot of things go wrong. The date is ridiculously bad, and Matt thinks he screwed up. Instead, Leah tells him that it's the most fun she's ever had on a date, and that she'd love to go out with him again.

In surprise, Matt blurts something like "What about going steady with me?" out, and again, thinks that it was a mistake (which it actually was). Leah doesn't realize this, and just kisses him on the cheek and says that she'd be glad to.

Being a tennis player, Matt is about to have the biggest competition of his life so far. He knows that there are college scouts in the crowd, and is feeling pressured. Leah comes along, saying that she's going to be his good luck charm. But, Matthew loses big time, and in quiet rage he storms back into the locker room. Leah follows him there, for once not caring about how improper it is for a girl to be there. She finds him beating himself up (whether or not this is physically is up to you.) and apologizes that she wasn't able to give him enough good luck. The thought of her thinking this calms him down quickly, and he says that maybe he used up all his luck when they got together. Leah takes this the wrong way, thinking that she is to blame for his loss. Matt quickly tries to redeem himself, but for once, words fail him, and to show her what he means, he resorts to letting his actions speak for him. He leans down, and they have their first kiss.