Eddie and Joys daughter, Allison (guest star Krysten Ritter), comes home for the holidays to celebrate New Years with her parents. When she gets some bad news from her boyfriend, Allison turns to her mother for help, leaving a snubbed Eddie perplexed. At the Woodcocks New Year's Eve party, Eddie lightens up his mood to impress his daughter, but as the clock strikes midnight and a new year begins, Allison realizes she likes her "big, dark, angry, wonderful dad" just the way he is.
Jeff is heartbroken and angry when Steph reveals that she won't be his Hockey Girl any longer. Eddie later muses that it's normal for new couples to lie and that they will eventually grow apart because of it, but Joy insists that she and Eddie are actually becoming more similar as they grow old together. As Jeff tries to accept that his wife is not the woman he thought she was, Eddie tries to prove to Joy that he is his own man.
When Joy accuses Eddie of being a pack rat, he and Jeff go through piles of ancient items from Eddie's past. The duo comes upon an old roll of film, which Jeff agrees to get developed. When Eddie sees the photos of himself and Joy having a great time in Italy, he is reminded of how the vacation ended and a moment he and Joy never discuss. In order to make things right, Eddie does all he can to relieve their trip to Italy right there in the suburbs of Philadelphia.
When Eddie and Joy visit Allison for parents weekend, they share a dorm room with a partying single father. When Allison lets them know her new major and next semesters plans, Eddie and Joy try their best to convince her to do otherwise but realize that their own mistakes led them to where they are today. Meanwhile, Jeff hires someone to help Steph tile the bathroom, which brings out the worst in her.
Steph gives Eddie and Joy a cappuccino maker that was a wedding gift from Jeffs mom. Joy loves the gift, but Eddie soon begins to resent Joy for not learning how to work the machine herself. When Eddie refuses to make Joy her nightly cappuccino, she makes a list of all the things she does around the house and comes to the conclusion that Eddie doesn't do enough.
When Joy and Allison (guest star Krysten Ritter) meet for Spring Break in Florida, Eddie is thrilled to have the house to himself where he can eat, sleep, wear whatever he wants and hang out with Cofeld (guest star Anthony Anderson). But when the week doesnt go exactly as planned, Eddie realizes how much he misses Joy. Meanwhile, Joy and Allison arent missing Eddie too much as they work-it on the beach.
When one of Eddies single idols comes for a visit, Eddie is in awe, while Joy is unimpressed by Webbys (guest star Ted McGinley) lifestyle of wild adventures and exotic travels. To Joy, Webby is running away from the one thing that can make him truly happy: a committed relationship. Ignoring Eddies warnings, Joy sets Webby up with Denise (guest star Tricia Fisher), who tames Webbys ways. When Webby is ready to settle down, Denise lets Joy know that shes not interested. Meanwhile, Jeff is miserable at the sight of his crying wife in an incredibly ugly shirt. Later, summer vacation has begun and Allison (guest-star Krysten Ritter) surprises her parents when she brings Doug (guest-star Tim Sharp) home. When Allison and Doug spend their days enjoying the summer, Steph convinces Eddie to join them. Meanwhile, Jeff and Joy feel left out and annoyed by their partners happiness but finally get convinced to join in.
Summer vacation has begun and Allison surprises her parents when she brings Doug (guest-star Timm Sharp) home. When Allison and Doug spend their days enjoying the summer, Steph gets Eddie to join them. Jeff and Joy feel left out and annoyed by their partners happiness but finally are persuaded to join in.
Eddie & Joy prepare for Jeff’s birthday dinner. Eddie doesn’t want to give lingerie as a gift. Eddie decides to give his own gift. At the birthday dinner with a few other couples, Eddie orders 2 desserts for himself. Steph tries on the lingerie. Jeff feels like Eddie doesn’t pay any attention to him. Jeff’s feelings are hurt when he realizes only Joy gave him the gift. Steph gives up on trying having a romantic evening. Eddie gets a perfect bottle of wine for Jeff which Jeff likes. Joy finds out that Eddie gave Jeff a special $1,000.00 bottle of wine she’d been keeping in their house. Eddie and Joy try to get the bottle of wine back and Jeff finally realizes that Eddie is trying to retrieve it. Joy and Eddie get kicked out of the Woodcock’s house, but Jeff eventually gives the bottle of wine back and the two of them bond over a shared drink.
When Joy accuses Eddie of not being able to express his emotions, they enroll in a couple's seminar to strengthen their relationship and help Eddie get in touch with his feelings. During the retreat their teacher, Dr. Friedman pushes her new age therapy leaving a bad taste in their mouths. Meanwhile, Kenny tries to help Eddie get in touch with his sensitive side and Jeff admits his sensitivity to Steph.
When Eddie takes his car into the shop, he decides it's time for a new set of wheels and purchases a red convertible sports car. Joy recognizes that Eddie's passion for his new car is part of his mid-life crisis, so in a play for his attention she flirts with her co-worker. Meanwhile, Kenny buys Eddie's old clunker and tricks it.
When Eddie and Joy spend a romantic night out in the city, Joy becomes enamored with city life and decides they should move downtown. Eddie tries to convince her to keep their house in the suburbs, but a visit to a new downtown loft development tempts him with fancy modern conveniences and causes him to reconsider his decision.
Joy discovers that Eddie has been hiding his favorite meatball-sandwich shop from her. This helps her come to the realization that they can't keep secrets from each other anymore because they've been married so long and seem to know everything about each other. Meanwhile, Steph's comments about her less-than-mysterious marriage prompt Joy to propose that she and Eddie come up with a new secret in hopes of spicing things up.
After Kenny's ex-wife kicks him out of their house, Eddie invites Kenny to stay with him and Joy. Eddie quickly realizes that Joy is a lot nicer when Kenny is around, so Eddie tries to get Kenny to stay with them longer, but Kenny's annoying habits have Joy trying desperately to reconnect the estranged couple.
Kenny freaks out after losing his swim trunks at a water park and his new girlfriend notices he isn't circumcised. When he decides to go under the knife, Joy is impressed by his efforts to please a girl he hardly knows and badgers Eddie to do more nice things for her. Eddie tries to get Kenny to back out of his decision so he won't have to accompany Joy to six weeks of musicals in the park and takes him to a bris so he can see what circumcision looks like.
Eddie and Joy's daughter, Allison, comes home from college for a visit. She and her hippie boyfriend argue and decide to break up, which is fine with Eddie until he finds out that Doug is wealthy. Eddie and Joy then try to get the two back together by inviting Doug over for an organic dinner feast. Meanwhile, Kenny just wants them to get back together so he can get his bedroom back.
Joy's fun and beautiful new friend Eileen also happens to be Eddie's ex-girlfriend. At first, the friendship doesn't seem to be a problem until Joy invites Eileen over to the house and Eddie gets himself in trouble by reminiscing a little too fondly about the past. Meanwhile, Kenny thinks he's doing something nice for his new girlfriend by babysitting her kids, but doesn't realize she may be using him.
When Eddie and Joy befriend Stephen (guest star Nealon) and his wife Simona, Eddie clicks with them right away, which causes Joy to feel left out. In an effort to win Joy over, Eddie coaches their new friends on her all her likes and dislikes. Meanwhile, Kenny starts a new job as a supermarket sample salesman only to realize that sample distribution can be a competitive biz
When Allison's boyfriend Doug is hospitalized, she rushes to his bedside only to be surprised with a proposal. No one is more surprised by their daughter's engagement than Eddie and Joy who plot to put the brakes on wedding planning. Meanwhile, Kenny tries to get Eddie's car repaired without success.
Eddie and Joy make the wrong impression on a newlywed couple while on vacation and Joy goes out of her way to try and convince the young bride that wedded life is bliss and not how they made it seem. Meanwhile, Kenny and Doug start spending time together, and Allison becomes jealous of their new friendship.
With Eddie's brother, Charlie, and his new boyfriend, Terence, coming to visit, Eddie isn't exactly looking forward to a weekend of wine-tasting and antiquing. Much to Eddie's surprise, though, he hits it off with Terence as they both opt to watch football over participating in the planned weekend activities. When Charlie breaks up with Terence, Joy sides with Charlie and ends up questioning her relationship with Eddie.
When Joy urges Eddie to get a check-up from their doctor, Simona (Susan Yeagley), Eddie becomes enamored with her and her husband, Stephen (Kevin Nealon), and their seemingly perfect life. Joy becomes annoyed when Eddie becomes ardent about taking Simona's advice, even though Joy has been nagging him for years, and decides to prove to Eddie that Simona isn't as perfect as she seems.
When Joy gets angry at Eddie for forgetting her birthday, she decides to cash in on all the coupons he has given her over the years for massages, pedicures and chores. Meanwhile, Kenny convinces Eddie that he needs to surprise her with a handbag in order to be forgiven. Unfortunately for Eddie, Joy decides to return the handbag and finds out the hard way that it's a fake.
When Joy suspects Eddie of keeping secrets from her, she decides to launch an investigation. Eddie turns to his friends Kenny and Karl for advice, and decides to give Joy a fake story in hopes of appeasing her.
Eddie and Joy's free-spirited daughter, Ally, returns from a trek in the Ecuadorian rain forest with her new husband, Doug. When Ally and Doug decide to set up camp in a trailer in the Starks' backyard, they ultimately ruin Eddie's plans for installing a Jacuzzi. Meanwhile, Eddie and Joy attempt to overcome their dislike of Doug and accept him as a member of the family.
When Joy and Eddie meet their rather unconventional new neighbors, Tommy (guest star Gottfried) and April Campbell, Eddie can't seem to get the idea of being with a younger woman out of his head. Meanwhile, Eddie and Joy hold a yard sale, and the new neighbors want to buy everything they're selling.
Eddie feels self-conscious when Tommy (guest star Gottfried) and Mr. White (guest star Mull) boast about their endowments, so Joy does her best to convince him that being average is just fine. Meanwhile, Doug and Ally have their first sonogram, and it appears that their unborn son doesn't take after Eddie.
When Whitey decides to throw a surprise party for his 93-year-old grumpy uncle, his party guests are surprised to discover that Whitey is a hoarder and his house is overflowing with junk. Meanwhile, Eddie is in a rush to get to the party but Joy, Doug and Ally all take their time getting ready to go.