Tommy confronts his sister, who had told him that his girlfriend died while he was in prison. Christy is still very much alive, and Tommy, still in love, rushes to her apartment.

When Christy’s boyfriend shows up, Tommy is left in confusion and he needs to make a quick exit! He then has to visit the probation office, where at least he seems to be striking up a good rapport with his probation officer’s son.

The probation officer saves Tommy's job at Pirate Burger, and this time he’s entrusted to make a delivery. He uses the opportunity to try to make contact with Christy again.

There’s a surprise in store when Tommy’s food delivery turns out to be for somebody he already knows.

When Christy doesn’t pick up her phone, Tommy goes to see her and finds a party in full swing at her place. It’s her engagement party, prompting Tommy to seek some answers from Christy and plead with her to come back to him.

Tommy’s sister urges him to forget Christy. Tommy audaciously breaks into his probation officer’s apartment while she and her son are away.

Tommy’s old criminal associate, Gray, shows up again with a seriously tempting offer for Tommy. Tommy, resolute, attends another meeting with his parole officer, who seems to have had a change of heart about his work options.

Buoyed by new job prospects and fresh hope, Tommy calls Christy again to ask her not to marry Frank. Christy has her own idea of how to resolve the situation, and comes to Pirate Burger to discuss her idea with Tommy.

The painting job is going well at the judge’s house, but Tommy doesn’t expect his probation officer to drop by, and even less the personal invitation that she extends to him.

Tommy enjoys his time with Angela as they watch Ethan’s baseball game, and she relaxes enough to reveal some secrets about her past. Tommy arrives home on cloud nine to find his sister waiting for him in the front yard.

Tommy’s grandma suffers a shock when the lie that his sister told her has unexpected consequences. Tommy and his fellow ex-con painters are rewarded for their good work at the judge’s house, and Angela is the first person Tommy wants to tell.

Tommy arrives home from work to find Angela waiting for him outside, and she has something to say that sparks a breakthrough in their relationship.

Tommy’s date with Angela doesn’t begin as he had hoped—in fact, she’s furious with him. There’s been a theft at Judge Pierce’s house and as far as she’s concerned, he’s responsible. As Tommy suspects, his ex-con painting buddies are involved.

Tommy returns the ring, but he’s not out of trouble. As the other ex-cons congratulate themselves on their good deed, Tommy is rejected by Angela and—adding insult to injury—soon finds himself under arrest.

Tommy’s criminal ex-associate Gray comes to his rescue, and soon Tommy seems convinced to work with him again. Tommy’s sister is appalled at the idea, and tells him so in no uncertain terms. When Ethan stops by to see him, Tommy is no longer at the house.