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.