Bobby and Liz break the news of their secret engagement to their families and each gets a less than warm response. In fact, Bobby's conversation with his folks ends with him moving into Liz's parents' guest house. Naturally, this doesn't thrill Philip and Simon, but at the risk of losing Liz completely, they agree to the situation temporarily until Bobby can work things out with his parents.
When Liz observes Bobby encouraging a friend to lie in order to break up, she questions his sincerity in their own relationship. In order to prove that he's changed and that he really loves her, she challenges him to find all the women he's dumped in the past and tell the truth about the break-ups. But Liz's plan may backfire when Bobby reconnects with the seemingly ""perfect"" girl.
Bobby accidently breaks Philip's cappachino machine and calls Mace to come and fix it. Simon comes home while they are trying to and they frantically try to finish fixing it before Philip gets home and freaks out.
When a client unexpectedly gives Philip tickets to a Red Socks game, Bobby sees it as an opportunity for family bonding and convinces Philip and Simon to invite Mace. But Mace's idea of how to watch a ballgame is quite different from Philip's and Simon's. Meanwhile, Liz tags along with the O'Neil women to a basement sale that's more like a battlefield.
Mace learns a lesson about stereotypes when he takes ill and is treated by a doctor who happens to be gay. Philip learns a similar lesson when his longtime friend and party planner, Joffrey, makes his own startling confession. Meanwhile, as their Halloween party approaches, Philip and Simon disagree about continuing their long-held traditions, and Liz wants to shed her ""cute"" image.
When Uncle Paddy O'Neil passes away, Liz offers comfort and support to Bobby by attending the wake — even though she's never seen a dead body before. In her angst, she forgets to drop off the key to the bar for the fill-in bartender and calls upon Simon and Philip for help. Meanwhile, the O'Neils return from the wake to find Philip and Simon hosting a karaoke challenge, which infuriates Mace — until he sees the day's receipts.
Philip and Simon initially oppose State Senatorial candidate Charlie Carson's plans to tear down an historical theatre, while Mace supports the politician's plan to build a hotel in its place. But Mace questions his support when he learns that Carson supports gay marriage, which causes Philip and Simon to change their minds and support him.
In an effort to get their families to join in the celebration of their upcoming wedding, Bobby and Liz convince their folks that the other's family is throwing an engagement party. Instead of working together, the families get competitive and try to outdo each other — which causes Liz and Bobby to flee to Vermont in frustration. Afraid that the young couple has eloped, the parents embark on a road trip to stop them — but a road trip with Mace and Philip is anything but a smooth ride.
Thanksgiving turns into a fiasco when Liz invites Mace's overbearing mother Colleen to the dinner. A web of deception begins when Mace tells the very conservative Colleen that Philip and Simon are Liz's uncles—instead of her dads. Meanwhile, Philip spins a tale of his own when he tells his stuffy decorator that Liz's future in-laws are wealthy.
When Audrey shows up with an unusual abstract painting that everyone agrees is awful, Mace sells the painting to Philip while she's away. Philip has good luck in selling the painting at his gallery, but when Audrey learns of the transaction, she's furious and demands that Mace and Philip get her painting back. What they have to do to get it back from the blind man who purchased it is anything but pretty.
Bobby and Liz's families are trying their best to blend their very different styles of celebrating Christmas when a Christmas Eve delivery to Philip and Simon's house injures ""Santa"" Mace. And Bobby feels pressure to compete with the lavish Christmas gifts that Philip and Simon have planned for Liz.
Bobby finds out Liz has discussed their sex life with her dads.
Philip hires Mace to pose as a typical American couch potato. But when he grows tired of eating chips and watching sitcoms while on display, it's left to a famous television personality to take his place (Ed McMahon). Meanwhile, Audrey and Simon become best buddies while working together to create a recipe for the perfect sauce.
When Simon asks Audrey to make costumes for a small musical theater production benefiting gun control, Mace is furious to find out that she is involved with the show at all. But when both of the leads have to be replaced at the last minute, Audrey and Philip can only hope for the support of their own leading men.
Mace's longtime friend, Dan, visits for a planned fishing trip, but before the fishing fun can begin, the two men have old scores to settle. Meanwhile, Maddy has eyes for Simon's new teaching assistant but fears that he may be out of her league. Simon concocts a plan to make the seemingly unlikely love connection.
When a TV show plans to air a ""Where Are They Now?"" special, the O'Neils discover that Simon used to be a member of an 80s one-hit-wonder boy band. Mace, desperate to become president of the local merchants association, promises that he can reunite the band for the Valentine's Day Winter Carnival. As Mace and Simon are consumed with the band's reunion, Audrey and Philip's Valentine's Day hopes are cast aside. Meanwhile, Bobby panics when he can't come up with an original plan for a special Valentine's Day with Liz. Valentine's Day-themed episode.
Mace and Audry want to have the reception at Lenords but Phillip and Simon want to have it at A fancier place. IN the end they decide to have the wedding at Lenords. Phillip and Simon agree because Mace said that he would take Phillip to the Eugene O' Neil Club. Bobby and Liz agree on a 16th June but then Bobby says its too soon
Philip is very excited to be seenig the oscars, but when he and Mace accidently glue their hands together, they have to go to the Emergency room. Meanwhile, Audrey upstages Simon with her catty comments about the stars on the red carpet.
A sexy park ranger (guest star Brooke Burke) helps Philip and Simon even a score with Bobby at his camping bachelor party; Liz's bachelorette party becomes a showcase for pole dancing.
Philip, Audrey, and Madddy go with Bobby and Liz to register for their wedding while Simon and Mace try and put together a crib. While shopping, Bobby picks out the wrong Bowl so Liz banishes him to a room with a bunch of other guys who are registering for their weddings too. He bonds with them and they watch TV. Audrey goes to see Dr. Bob, a television star who does therapy to get him to sign her book. Maddy hates her bridesmaid dress and her mother thinks it's nice. They have a small argument on who's right about what kind of girl Maddy is and Maddy waits in line with her mother to see Dr. Bob to prove she's right. Philip freaks out about a gravy boat on display not being able to be sold and climbs on to the top shelf and won't come down. They call in Dr. Bob, who says it's not the gravy boat that has Philip so upset, it's losing Liz. But Dr. Bob (with the help of Simon--who with Mace went to the mall to get a piece for the crib) and Liz make Philip feel better and come down.
Liz and Bobby's adoption of a stray dog sparks a debate between the families on parenting styles. The O'Neils flashback to their strict disciplinarian ways with Bobby and Maddy, while Simon and Philip flashback on their gentle, nurturing approach with Liz. Bobby and Liz realize that they may have to compromise on some important decisions once they become parents.
A fight erupts between families over the text of Liz's and Bobby's wedding invitation -- specifically, whether or not to mention Philip's and Simon's sexuality. Meanwhile, Bobby's priest, Father Joseph, tries to talk Liz out of the marriage.