Bob gets a dressing down from Owen after he innocently buys Alicia a beautiful dress while on a shopping spree. After skirting the issue for a few days, Owen tries to one-up Bob by buying his fiancée a dress himself; but he doesn't have Bob's terrific taste.
Pressure from Alicia to plan their wedding has Owen neglecting his work and Bob -- who, tired of catering to his partner's schedule, proposes changes in their work habits, such as not working together anymore.
To celebrate the anniversary of the first time they made love, Owen and Alicia plan a weekend getaway to the hotel where it all happened, but their romantic trip hits a few roadblocks: their old room has not aged well.
Owen can hardly mask his skepticism when his older brother Cameron pays him an unexpected visit and promises to make amends for a life straight out of pulp fiction; meanwhile, Bob dates Alicia's friend only to discover that they dislike each other on sight -- and that she is his ex-girlfriend's therapist ("Boy, you must not be very good!").
Upon learning that his estranged father is making a Christmas Eve stop in San Francisco, Bob goes to great lengths to snow his dad into believing that his life is perfect. Unfortunately, the stop turns into a brief visit at the airport, giving Bob his 14 minutes to feign.
Bob's New Year's Eve date Danielle can't seem to forget an auld acquaintance -- namely, her ex-beau David -- so he resolves to intoxicate her with his charms by throwing a party. Meanwhile, Heather's in for a big surprise: since New Year's is her birthday, she assumes the party is a surprise for her.
Alicia is less than thrilled when her dad goes out on his first date following his divorce -- with a younger cocktail waitress from the bar Owen and Bob took him to. Meanwhile, Bob tries to help Heather overcome her addiction to nasal spray.
It's a blueprint for disaster when Owen decks a rude contractor for making an off-color remark about Alicia. But Owen's guilt over the incident is offset by Bob's delight, improved productivity at the job site, and Alicia's reluctant sexual excitement at her fiancé's new-found machismo. Meanwhile, Heather falls for the hunk temporarily replacing the despised "sandwich lady," but can't get him to notice her.
Owen, Alicia and Lolie are aghast when Bob leaves their engagement party for a sexual tryst with Alicia's friend Charlotte -- who is herself getting married in a week -- and Bob is infuriated by their assumption that he is too nice to go through with it. Trouble is, they're right; and after Lolie taunts him with the fact, it's they who tumble into bed together.
After Owen and Bob sign restaurateur Max Lobster to a lucrative contract, Leavitt takes the account away from them -- so they quit, sending Owen into a depressive tailspin nine days before his wedding.
As their big day approaches, Alicia becomes obsessed with the superstition that Owen should not see her on her wedding day; and Bob surprises Lolie with a proposal, but is not prepared for her reaction ("Oh, God! No!").