Alicia's ready to tie the knot - around Bob's neck - for interfering in her romance with Owen and their plans to pick a wedding date.
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.
Owen trips down Memory Lane when his secret college crush comes to gown; unfortunately, Bob tells tales out of school to Alicia - then falls for Janet himself.
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.
Alicia suspects Owen may by trying to pull the wool over her eyes when he asks sheepish about winning a BAAAA (Bay Area Architectural Association Award).
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 feels like he's been thrown to the wolves - or rather, to the Wolfes - when Alicia's co-worker Cindy Wolfe and her argumentative husband hire him and Bob to redesign their house.
Owen and Alicia's plans for a romantic ""anti-Halloween"" are interrupted by relentless trick-or-treaters and Bob - who's brought an entire party with him.
Owen learns he can't fight city hall after Alicia - shocked by her parents' announcement that they plan to divorce - demands he take her there at once to get married.
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!"").
After jumping through hoops to fight the boys' club mentality at work, Alicia tries to beat her male colleagues at their own game by joining them at a sports bar. Meanwhile, Owen and Bob try to get their secretary a raise - and wind up paying for it themselves.
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.
Since Bob's New Year's Eve date can't seem to forget an old acquaintance - namely, her ex-beau David - he resolves to intoxicate her with his charms by throwing a party. Meanwhile, Heather's in for a big surprise: New Year's is her birthday, and she assumes the party is a surprise for her.
A potential caterer for Own and Alicia's wedding turns out to be Bobby's former baby-sitter, a beautiful woman on whom he had a major crush.
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. However, 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.
As Valentine's Day nears, Bob's new love (Aniston), a CPA, fazes him with a request to shave off his goatee; the holiday finds Owen felled by the flu and falling down with exhaustion.
Alicia's dream of rolling in dough may knead rethinking when she runs into her boss while returning the expensive pasta-maker he sent as a pre-wedding gift.
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.
Owen and Alicia aren't happy that their best friends, Bob and Lolie, will both be coming to the wedding without a partner. So they plot to set them up, respectively, with Diana, the wedding cake caterer, and Dr Joe. Of course, they don't realize that Bob and Lolie are already sleeping with each other. At the cake tasting, things don't go exactly to Owen and Alicia's plans, but at least Bob and Lolie's secret is still safe.
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 the 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!"").