After his wife leaves him, Ben tries to get back into the dating scene while making time for Luke, who's more interested in girls than in dad's idea of fun. The culture clash is exacerbated when Seamus calls from Ireland to announce that he's visiting. While at the airport to pick his dad up, Ben meets Madeline, who recognizes him as the famous architect and gives him her card. Ben brags to his friend and partner, Alex, that a woman gave him her card. Alex and receptionist Wendy beg Ben to hurry up and call her already before she loses interest. But Ben discovers he lost her card and decides to forget it -- until Madeline calls him and asks him to dinner. Ben suddenly remembers that the date he just agreed to coincides with his taking Luke out to ""The Lion King"" musical. Alex and Wendy won't let Ben stand Madeline up, so Ben gets Seamus to take Luke. But Luke angrily cancelled a date of his own for his father -- and didn't want to go to ""The Lion King"" in the first place. At dinner, Be
Ben is rattled when he sees Luke playing basketball with Serge, Vonda's new boyfriend, right after telling his pop he was going to a friend's. Ben has the Serge talk with Luke, and learns that Luke asked Serge to play with him in a two-man tournament -- which happens to be a father/son game. Luke just wants to win, but starts to take Ben's feelings into consideration. Vonda calls Ben to lay some blame when she learns that Luke dropped out of the game with Serge. Ben begins to question his usefulness as a parent, so he meets with Vonda to clarify why Luke dropped out. Then he decides to get more involved in Luke's life by taking Serge's place in the game -- even though it's that same night. Luke is worried that Ben is going to humiliate him, but goes ahead with it anyway because of Seamus. After a chat with Seamus, Ben begins sharing the same fear as Luke, after which he bails out and lets Luke reinvite Serge. But when Serge ends up getting them disqualified, Luke makes amends with Ben
Ben learns that the pub's bartender has been deported, and reminds Seamus that if he wants to stay in the country, he should check up on the status of his visa. Seamus decides to write down his memoirs to impress the I.N.S., just in case he does choose to stay -- even though Ben doesn't necessarily want him to. Alex and Wendy suggest Ben let Seamus' visa expire quietly, so he can get kicked out. But a guilt-ridden Ben goes down to the I.N.S. to inquire about his father -- only to find out that his visa has already expired. Since Seamus is mad at Ben for wanting his space back and possibly getting him deported on purpose, he goes to stay with Alex. Ben reads Seamus' memoirs (which are more depressing than Angela's Ashes), and changes his mind about wanting Seamus to leave. Ben then lays down some ground rules and agrees to sponsor Seamus, so he can stay in the country until he gets citizenship.
When both Seamus and Luke run dating circles around Ben, Wendy decides to offer her matchmaking services to him. But Ben doesn't want to go out with Wendy's blind date, who's a dermatologist and, like Ben, isn't looking for a serious relationship. He does want somebody to check out a mythical freckle of his, though. After sharing his news with Seamus and Luke, Ben goes to Wendy's dermatologist, Dr. Ivy Castelli, for his ""checkup."" The next day at the office, Ben admits to Alex and Wendy that he and Ivy slept together. And worse, he let ""I love you"" slip out. Confounding the problem is a gift basket Ivy sends to Ben that returns the sentiment. Ben pays a visit to Ivy's office to clarify what he said, and how he still isn't looking for a serious relationship. Thus ends Ben's 24-hour office visit. Meanwhile, Alex pesters Wendy to fix him up with somebody, so she gives him her therapist's number.
Ben and Alex meet New York's ultimate bachelor, Sebastian Jones, whose swanky apartment they're renovating. Believing he gets it regularly, an awestruck Alex puts on a cool face to impress the guy, while Ben won't initially admit to feeling sexually inferior -- even after Sebastian mentions his invitation to Fashion Week, and how he can't go this year. But an insensitive comment from Luke about how Ben has no life changes his tune, and he and Alex return to Sebastian's apartment to get the invitation and go to Fashion Week in search of coolness. Before they leave, two of the models, Kim and Jade, drop by to see Sebastian, and Ben and Alex decide to use the chance encounter -- and the invitation -- to make a move on them. The bouncer, Jake, lets Kim, Jade and Ben in, but won't let Alex in because he finds him too ""eager."" Ben comes back outside to tell the bouncer Alex is with him, but instead of getting Alex in, Ben gets himself out. Later at the pub, Ben decides that sort of bachelor'
Ben has to contend with a basket case who won't leave him alone after a disastrous date filled with tears -- hers. Needing some time off from the dating scene, he goes out to dinner by himself, and winds up running into Vonda and Serge. Ben and Vonda compare notes, and discover that Luke has been lying to both of them about his whereabouts. After Ben brings Vonda home to his apartment, they call up Luke's girlfriend's house and find out he spent the night there. Then they start reminiscing about when they were married, and soon end up kissing each other -- which Luke catches upon returning home. When Sandy, the basket case date, drops by the office to see Ben again, he tells her they can't go out anymore because he's thinking about getting back together with Vonda. But Vonda doesn't feel the same way. Ben has a talk with Luke about what he saw and what he did. Luke learns that his parents aren't getting back together, and Ben learns that Luke's girlfriend's mother has forbidden him fro
Ben is disappointed to learn Luke tricked Seamus into signing his straight ""C"" report card. Ben relays this to his friend, Liza, the dean of NYU, along with his fear that Luke won't be able to get into his dream school -- which just so happens to be NYU. Liza persuades Ben to teach an architectual course there with the side perk that it'll be easier for Luke to get in with poor grades if his father happens to be faculty. One of Ben's new students, Sara, tells Ben how much he inspired her not to drop the class. Ben finds out the sad truth -- Luke doesn't want to go to NYU anymore, he wants to go to the U of Hawaii. Sara changes her major to architecture, and freaks out when Ben tells her he's planning to quit because of his son. But Liza manages to talk him out of it. Alex and the company foreman, Carl, tell Ben he should make a move on Liza. Ben decides to let go of his dream of both father and son going to NYU. Seamus enrolls in Ben's class -- where he disturbs things by taking pictur
Ben doesn't approve of Luke's alternative girlfriend, Jane, because she has a tongue ring. Hoping to get Luke to dump her, Ben tries to fix him with one of his well-to-do students -- whose mother happens to be carrying a torch for Ben. Meanwhile, Seamus becomes alternative himself when he changes his hair color.
Jesus the doorman lets Ben in on a little secret: a couple who live in the building's penthouse, Troy and Alice Wolfe, are moving out, and Ben can have it cheap if he befriends the Wolfes before they put it on the market. And if Ben can have the penthouse, then Seamus can have his own wing. And then Alex can have Ben's apartment. And then Carl can have Alex's apartment. Ben decides to invite the Wolfes to dinner to try to butter them up, but he has to find a place to hide Bailey -- who bit the Wolfes' dog, and who Seamus said they had put to sleep. So Ben dumps Bailey off at Alex's, even though Ben won't invite Alex to the party. Bailey eats half of one of Alex's valuable baseball cards, so Alex drops by the dinner anyway to voice his displeasure. Then Carl just shows up, even though he wasn't invited either. Next, Jane and her boss, who are catering for the dinner, get into a brawl when their van gets towed -- with the food still in it. Troy and Alice arrive last, and quickly provoke
Ben recommends Seamus get a massage to cure his stiff neck, while Luke wants to invite a girl to the apartment.
The building Ben is currently restoring is in the market for a bricklayer. Since Seamus used to work as a bricklayer back in Ireland, Ben talks Alex and Carl into putting his father back on the payroll. But no sooner than Seamus has got the job than he's convinced the entire crew to go on strike. Meanwhile, Luke refuses Ben's help on an art project for school.
Ben meets a woman named Mary, who is the daughter of Seamus' rival.