Peter and Annie Brennan are anxious to begin celebrating life as a couple again now that their children are all grown up, but it just doesn't seem to be in the cards. Their youngest , Tim should be graduating from junior college, but instead he's moving in with the ""older"" woman-next-door -- his mom's thirty-something tennis partner, Maggie. Their eldest, Todd is the apple of his dad's eye and is engaged to a great girl - and having an affair with yet another great girl. And daughter Sara the over-achieving family success story, is in the midst of a major emotional meltdown.
Annie attempts to break up Tim and Maggie by aggressively inserting herself into their personal life. Meanwhile, Peter's frustrations grow when his ""favorite child"" Todd cannot decide whether to marry his fiancÃe Jeanie or date Susan , the woman with whom he's been having an affair. When the family believes Todd has finally made his decision to leave Jeanie, he brings her to dinner with the family creating an uncomfortable situation for everyone.
As Sara's dating drought continues, the Brennan family decides to get involved and set her up on two dates. Peter and Todd set Sara up with their patient Stu (guest star Richie Keen, 'The Third Wheel') and Annie and Tim introduce her to a guidance counselor. After the dates, Sara is excited for the prospects of a second date with both men. However, when the Brennans find out that neither man is interested in a second date with Sara, they must figure how to best tell her the truth.
Peter and Annie have always taken pride in raising their three children and have looked down upon their friends the Michaelsons for the way they raised their children -- their son just was released from prison and their daughter is very promiscuous. However, when Peter and Annie realize they are being compared to the Michaelsons because of Tim, Todd and Sara's problems, they are forced to take drastic measures to restore their reputations.
When Peter and Annie try to convince Tim to go back to school, he decides to get a job instead. However, Tim soon realizes that his parents are thrilled with his performance in a mindless job and that he is miserable at work so he takes a stand against his parents and goes back to being happy with his life...unemployed.
Sara decides to become a rebel after she tires of trying to please her parents by leading a responsible life. With the support and advice of her brothers, Sara carefully plans her rebellious actions without realizing that she'll end up in situations she was not prepared to handle.
When Tim and Maggie try to adopt a dog, they are shocked that the adoption agency won't give them a puppy because their lifestlye lacks stability. Meanwhile, Todd breaks up with another girlfriend, leading Annie to question whether her son treats women well.
When Sara brings home a male friend Peter and Annie convince her to see him as more than a friend. Meanwhile, after Tim celebrates his 21st birthday with Todd he feels guilty of his actions and confesses to Maggie about his evening out. In the end, Maggie surprises Tim with her recent actions as well.
Peter and Annie decide to do an early Thanksgiving after learning that Tim intends to spend Thanksgiving with MaggieÓs family and Sara will be out of town on business on Thanksgiving day. As constant mishaps occur throughout the planning of their Thanksgiving it makes the day typical of family gatherings.
With the kids finally moved out of the house, Peter and Annie decide to make some Halloween mischief of their own. However, their secret time alone together is interrupted when the kids show up unexpectedly, forcing them to do some quick explaining. Jeff Davis, Melanie Paxson and Tyler Francavilla also star.
Just as Peter and Annie begin to accept Tim and Maggie's relationship, Maggie's ex-husband Bill comes into town for a visit and learns that Maggie and Tim are more than just neighbors. When Tim and Bill challenge each other to win Maggie's heart, Tim takes his devotion to an unexpected level.
Peter's mother, Lois, who visits town and immediately causes problems for the Brennans. As Susan and Todd plan Tim and Maggie's engagement party, Lois gives them added work when she insists on them also celebrating her birthday with a special Top 10 list of why sheÓs such a special grandmother. Meanwhile, Lois creates tension between Annie and Tim after she criticizes their close relationship.
Sexual tension complicates Todd's relationship with a new employee. Peter and Annie sense trouble in Tim and Maggie's relationship.
After witnessing the growing friendship between her mom and Alex, Sara starts to spend time with Annie's friend Barb in the hopes of making her mom jealous. Meanwhile, after Tim moves back into his parents' house, he and his dad, Peter disagree over the ""house rules"" and settle their disagreement with a game of pool.
When Peter and Annie team up with the Millers to establish a new friendship, things don't go as expected. Meanwhile, Tim uncovers a secret that might have changed Todd's life had Sara not hidden an important letter pertaining to his college career.
Peter and Annie initially think it's the best day ever -- Sara begins dating a tennis instructor and Tim finds a job. But things aren't as rosy as they appear on the surface... While showing Peter some tennis moves, Sara's new beau accidentally kills her beloved pet bird, Eric, and Peter convinces him not to fess up. Meanwhile, Tim's job is helping an attractive older woman around her house (and in the bedroom). Tim fears that he has an unhealthy obsession with older women, though Todd tries to convince him otherwise, so Alex takes him out to meet some women his own age.
After Peter grosses out Todd by revealing that he and Annie broke their headboard during sex (the night the Berlin wall came down), he and Annie decide their sex life needs a boost... which leads Annie to the porn section of the video store. Meanwhile, Todd tries to get even with a rival dentist, Dr. Fishman, by having Tim dress up as a tooth and hand out flyers in front of Fishman's office, but it results in Tim getting beat up (and brushed) by another tooth.
Suddenly aware that their daughter is keeping something from them, Peter and Annie make the mistake of assuming Sarah's secret meetings with a woman means she's gay. However, the truth behind their clandestine meetings is much more than any parent could bear. Meanwhile, Todd steals a beloved t-shirt of Tim's and Alex incites revenge, prompting Tim to break into his brother's apartment -- but Todd's prize possession -- a photo of a naked woman -- is a secret that is best kept hidden.
Peter receives a juicer from Annie for his birthday -- that she really bought for herself. Peter tries to return the appliance but finds that it's already been used, so he goes out of his way to hold it over Annie's head. Meanwhile, Todd reluctantly agrees to go to one of Sara's office parties, then has to be the bearer of bad news when he discovers that her coworkers loathe her office parties. Tim becomes frustrated that Peter can't work the digital camera that he gave him for his birthday.
Annie gets a part in a community theatre production, but Peter's jealousy of her handsome costar results in the play being canceled, so an angry Annie tricks Peter into going to couples therapy. Meanwhile, Sara gives Tim a less than glowing job referral, so when he gets fired, Tim goes out of his way to prove Sara wrong. Todd becomes self-conscious about being less intelligent than Sara.
Annie sets up Alex with a hunky hairdresser, whom Sara believes is obsessed with someone else -- namely herself. Overcome with jealousy, Todd is forced to confront his feelings for Alex. Meanwhile, Peter is dumbfounded and loses all hope that his son will find a job when Tim goes to the doctor and is diagnosed with stress. Concerned for her youngest son's well-being (and her husband's state of mind), Annie plays an ace that she's been keeping up her sleeve.
Annie's birthday wish is for her children to write a letter about all the important things in their lives, but Tim rebels against his mother's nosiness -- leaving Annie to feel betrayed and scorn her son. Meanwhile, Peter declares war on his new neighbor - namely his daughter Sara - because of their disagreements over parking spaces and trees. Todd, now secure with his feelings with Alex, shamelessly tries to win her affection.