How Not to Live Your Life

Don joins a drama group to keep his mind off of Sam. He lands a plum part in Top Gun: The Musical, but he is disappointed with the casting of his character's love interest. Don schemes to replace the actress with Sam. His plan to keep Sam out of his thoughts isn't working. Will his attempt to make her his leading lady turn out any better?

In Don Does Therapy, Don thinks he's over Sam, but when he finds out that Brian is going to propose to her, he suddenly feels the interest rekindling. Deciding instead that he must have some issues to deal with, he chooses to seek a therapist. The therapist may not have time to do his work before Don tells Sam how he feels.

Don shows some sympathy for a homeless woman, Susan, bringing her home to give her a place to stay for the night. Susan is pretty and Sam suggests, in jest, that Don ask Susan out. It's true that when morning comes, Don doesn't want Susan to leave; so he takes her out for a day on the town. Their "date" has its ups and downs. Will it come to an amicable end?

In Don Meets His Maker, Don thinks he might need a hair transplant. Some confusion ensues, and Don's friends think he might need a transplant of another kind. Don enjoys all the attention he begins to receive as a result of their concern over his health. When Don figures out why they're being so attentive, will he give into the temptation to fake an illness for his own gain?

Don and his boss, Jason, meet two girls at the gallery where they work and take them out on a double date. Don's pleased to discover that his date, Felicity, is more open-minded than she looks. Don is less pleased with her parents' attitude towards him when Felicity takes the group on a weekend trip to her parent's country home.

Don dates a woman, Jenny, who doesn't seem to mind his bad behavior. But Jenny's accepting nature could be too good to be true. As Don grows closer to Jenny, he begins to see another side to her that isn't so attractive. When she and Don join up with his friends for a pub quiz, he isn't the only one who sees her less charming side.

Sam has a new boyfriend, and Don must cope with the realization that he ruined his chances at having a relationship with her. His love life is in shambles; and his career isn't much better. He pretends to have a new job but has to go to great lengths to keep up the ruse. It seems to have worked out to his advantage when he secures a better position, but more complications arise.