Don has blown his chances with flatmate Sam and to make matters worse she has a new boyfriend. With no career, Don comes up with an elaborate story about a new job to try to impress her. Things finally appear to be going his way when a chance encounter with high-flying executive Marcus leads to a promotion. Of course being Don, it's not long before it all goes wrong.

Things are looking up for Don as he has begun to date a sweet girl called Jenny. However, her behaviour starts to ring alarm bells as her moods swing from adorable to violent in an instant, turning Don into a battered and bruised mess. To make matters worse nobody believes him. The tension comes to a head during the local pub quiz. Don and Jenny join Sam and Brian's team. They are determined to beat arch rival Derek. Jenny hates losing. Is this a chance for Don to show everyone her violent side?

Don and his boss Jason socialise together for the first time in the form of a double date with two posh girls they met at work. Don learns never to judge a book by its cover, as his date Felicity is far from prudish. Everything seems to be going well until Felicity invites them to her parents' country house for the weekend. It's a world away from Don's life and he struggles to fit in. He also has some over-protective parents to contend with.

Don finds himself having a bad start to the week when he notices that his hair is thinning, He ends up booking an appointment with a specialist to discuss having a hair transplant. Things get worse for Don when he notices that he isn't the centre of attention after he is completely ignored he storms out. After Eddie discovers Don's letter about the transplant he ends up assuming the worst. Eddie, Sam, Brian and Mrs Treacher attempt to support Don when they think that he doesn't have long left to live and Don ends up making the most of the situation.

Don ends up surprising himself after he takes pity on pretty homeless woman called Susan. Sam ends up suggesting that he ask her out. When Sam returns home with Brian, she discovers Susan sitting on the sofa in their living room whilst Don runs her a bath. The following day Don doesn't want Susan to leave but after he offends her on a day out he tries to make it up to her by getting to know her friends better.

Miután észrevette Eddie színházi klubjának a Esőember című produkcióját, Don úgy dönt, hogy csatlakozik. A klub óriási produkciót készít a Top Gun: The Musical-ból. Időközben Brian még mindig várja, hogy Samtól választ kapjon a javaslatára, és annyira kétségbeesett, hogy még Don tanácsát kéri.