This is a list of all characters who appeared or were mentioned to have had a romantic relationship with Will.
Before the show
Diane is the only woman who Will had ever slept with. They later learned that she is an ex-girlfriend of Leo, which drove Grace extremely jealous.
Claire is Will's girlfriend in high school whom he went to senior prom with. They remained friends after he came out, and later asks him to father a child with her through in vitro fertilization.
Zack is the first guy Will went out with after coming out, though he ended up stealing Will's identity and travelling to Europe with his credit cards. Jack later admits paying Zack to go out with Will to boost his confidence.
Michael is Will's longest boyfriend, though they broke up prior to the series, whom Will once refered to as the love of his life. He runs into Michael again when Grace decorates his new apartment. Will tries to rekindle their relationship by expressing how much he has missed Michael, only to find that he is already living with someone else ("Hey La, Hey La, My Ex-Boyfriend's Back").
Peter is a guy who moved into Will & Grace's apartment building. Peter seemingly flirts with both Will and Grace separately and invites them to dinner, which the two think of as a date. They fight for Peter's attention, confused if Peter is straight or gay. They finally ask him, but Peter expresses his disappointment and does not answer directly, simply thinking they were just friends. He leaves saying "you're not my type" to either Will or Grace.
Charlie is a Scottish guy Will went out with for his boss Ben. Although Will seemed attracted to him, Charlie did not call for a second date, which confused Will.
Neil is a self-absorbed guy Will dated.
Matt is a sports reporter Will met at Banana Republic when Jack asked Will to speak "smart" through him so he could hit on Matt. They fail, however and Matt figured out it was Will he was talking to so they start to date. Will later found out that Mathew was still in the closet, introducing him as his brother. Matthew wasn't willing to come out, which was a deal-breaker for Will.
Paul is a guy Will dated because of his dog, Pepper.
Scott is a 23-year-old guy who works at the video rental store who Will reluctantly dates because of their age difference.
Chris is Will's "imaginary boyfriend" whom he frequently sees at the coffee shop but is afraid to talk to him. They eventually run into each other at the airport and introduces himself at the end of season three. Will, who is bound for Morocco, was inspired by Grace and Nathan's romance and changes his flight so he and Chris could fly to Loire Valley together. When Will returns from their trip, he says that they broke up because he couldn't stand him.
Robert is a ballet dancer Will dated briefly.
Phil is a guy with whom Will went to his apartment with while Grace and her date Bill are already there. They went out on at least two dates, where Will observed that he smells like wet dog.
Mitchell is a guy Will "fooled around with" shortly after breaking up with Michael, as his rebound guy. After sleeping with Curt from the gym, Will realizes that he is Curt's rebound from Mitchell.
Gavin is a closeted detective who helps Will after his laptop got stolen at the coffee house.
Kim is Leo's friend who he set up with Will for their Pumpkin picking day trip in the Catskills.
Barry is Karen's awkward cousin who appears in a four-episode arc during the fifth season.
Rudy is Barry Manilow's road manager.
Ted is only mentioned as a guy whom Will dated and even thought of moving together with. Will broke up with him after Grace said "mock turtle neck."
Edward is Karen's sexy Irish pansexual pastry chef Will is supposed to fire to cut back on expenses. However, Will and Edward end up having sex. They were supposed to go to Mantauk the next weekend when Will finds out that he has also slept with Karen and Rosario so Will fires him immediately. He considers "The Grand Illusion" by Styx to be the most seductive song known to man.
Desmond is a "blind" guy Jack set Will up on a blind date with for his TV show.
Bret and Brent
Bret and Brent are two flight attendants whom Will flirted with separately during a flight to London to get free stuff. He later discovered that they were a couple.
Will met James after going to the wrong theater dressed as Captain Von Trapp for The Sound of Music Sing-Along. Though they made a connection, Will left without asking him out because he did not want to seem desperate. James tried to follow him but was too late.
When Will visited Los Angeles, he ran into James at the hotel lobby. and learned that his visa is expiring and will soon be deported back to Canada. Will, not willing to let go of a possibly good relationship, advised him to marry Grace so he could get a green card to stay in the country. Grace and James do get married in a fake wedding but after a while, Will discovers another side to James, which is self-centered, offensive and cruel. Will arranges the papers so Grace can divorce James and send him back to Canada right away.</p>