Ben? Her? is the 23rd & 24th episode and finale of the second season, and 45th & 46th episode overall.
Will is seemingly content with his life; having taken a magazine quiz and supposedly having the five pillars of happiness intact (family, health, work, friendship and love). Grace, however, has none of the pillars, especially since she is still dating Josh with whom she has a lukewarm romance. Will invites Ben Doucette over for dinner and tells Grace to make nice with him, due to their animosity shared between them. While Will is on the phone with his boyfriend, Grace and Ben talk and eventually end up sleeping together in Grace's apartment. Will is annoyed, but remains passive-aggressive. Ben and Grace embark on a romantic relationship, even dancing together on the table at the firm. Grace claims that she finally has her five pillars in place. Will later discovers that Ben is seeing another woman.
Meanwhile, after returning from his date from Fernando, Jack discovers Rosario in bed with the gardener who she claims to be in love with. He is shocked at her infidelity, especially since it is their anniversary, and flounces out; their marriage evidently over. Jack demands money from Karen for being married to Rosario for a year, but Karen refuses to give him a cent, and they embark on a feud.
Will's pillars seem to be crumbling, with Alex becoming suspicious of his living situation. He tries to tell Grace about Ben's apparent infidelity, but Grace hushes him, telling him she doesn't want him to "chip away" at her relationships like he always does.
Will, frustrated by Ben for cheating on Grace, quits his job. He later regrets this when he discovers that Grace is still seeing Josh, and that she appears to be in a casual, no-strings attached relationship with Ben.
Meanwhile, Jack moves in with Will, bring Klaus and Guapo. Jack's presence angers Alex, who finally calls things off with Will over the phone. With Will's pillars falling apart, he decides to jet off to the Virgin Islands without telling Grace. Both Jack and Grace lament Will's leaving, both missing the glue that held them together.
Will seems content on the island, until it becomes evident that Ben has tracked him down; wanting to offer him his job back. Will requests a raise and a promotion, and remains on the island on business. He later discovers that he has a new client on the island: Karen Walker.
- Eric McCormack (Will Truman)
- Debra Messing (Grace Adler)
- Sean Hayes (Jack McFarland)
- Megan Mullally (Karen Walker)
- Gregory Hines (Ben Doucette)
- Shelley Morrison (Rosario Salazar)
- Corey Parker (Josh)
- Marshall Manesh (Mr. Zamir)
- Richard Gross (Frank)
- Gorden Owens (Servant)
- Michael Edward Thomas (Caribbean Houseboy)
- Pablo Cartaya (Fernando)
- Jo Marie Payton (Mrs. Freeman)
- This episode was split into two episodes for syndication. Some scenes were edited or removed in the syndicated versions.
- Grace reads that "Janet Eisenberg, 33, and David Bromberg, 35, are getting married." Janet Eisenberg is Max Mutchnick's real-life "Grace" and she and David were married that week.
- Stanley Walker's hand was played by executive producer/writer Jeff Greenstein.
- David Kohan and Max Mutchnick wrote Part 1; Jeff Greenstein wrote Part 2.
- Klaus von Puppy and Guapo appear in this episode.
- Title is a reference to the movie, Ben-Hur.
- Jack sings Fernando by ABBA to his date, Fernando.
- Ben and Grace dance to the song, "It Had to be You".
- Jack is referenced as reading Valley of the Dolls to Karen's children every night. The novel is about women who try to pursue their dreams but end up being dependent on amphetamines and barbiturates.
- When Jack moves in with Will, the theme from The Odd Couple plays.
There's something I need to tell you. Mommy and daddy... Well. We've decided to live apart. Now, this doesn't mean we don't love you. In fact, it was because of you that we stayed together as long as we did. But in this crazy, mixed-up world, how long can a marriage between a Salvadoran maid and a West Village singer/actor/dancer/choreographer last? — Jack, to Guapo and Klaus von Puppy
|Grace:||Obviously I didn't plan this thing with Ben. It just happened. It was just this wild, chemical ripping off of a pair of $50 panties kinda thing.|
|Will:||Thank you, Grace. That'll go next to the visual of my grandmother getting out of the tub.|
Love life? Gone. Job got in the way. Job? Gone. Friend got in the way. Health? Well, something's in the way. I may have to borrow some of that bran. — Will