David, a restaurant owner, has been holding a torch for his friend Susan, a cruise line executive, since college. Susan loves to meddle with matchmaking, but is upset when she accidentally finds a match for David. David is frustrated when Susan dates his womanizing younger brother, Thumper. Susan, completely over Thumper, realizes she's in love David, but thinks she's too late and he's already in love with her friend, Elena. When David finally admits his feelings for Susan, they live happily ever after... until next week.
Womanizing Thumper falls in love with Matt's ex-wife, Yancy, but she quickly rejects him when she and Matt decide to give their marriage one last try. Between the all-night lovemaking and the constant commuting between their two apartments, a physically exhausted Susan and David realize that it might make sense to move in together.
David and Susan are planning on moving in together, but can't decide on an apartment. Their real-estate agent, Carlotta, starts dating Thumper, but Thumper is scared by her obessesed ex-boyfriend Felix. David buys a ring to propose to Susan, but gets cold feet when he tries to propose. David's restaurant closes down after his chef falls in love and moves to France, and his rent is raised. He and Susan break up and he takes a job in L.A.
Thumper's platonic friend, Jamie, realizes that she has more than platonic feelings for Thumper, so they try dating, but from his side the sex is awful. Matt's sister, Heather, is all set to marry Rick, the guy who walked out on their wedding three year prior. Matt hates Rick, and when Heather gets cold feet and disappears on the day of the wedding, Matt's first reaction is to be happy. However, when he finally sees how upset Rick is at Heather's disappearance, he finds his sister and convinces her to go through with it because Rick does really love her.
Susan starts dating a magician just as David is coming back from L.A. for a few weeks because Matt needs his help with the hotel restaurant. David wants to rekindle things with Susan, but she turns him down. David turns down an old flame from New York that he runs into at the hotel who tries to seduce him in the jacuzzi. Susan's magician gets a job on one of her cruise ships, and leaves town. Thumper's old high-school girlfriend wants to have him one more time in her parents' bed before she gets married, but when her father walks in on them, he has a heart attack and dies. David buys the dead guy's restaurant and is in Miami to stay.