Will & Grace - Season 2 (1999)

Grace is jealous when her mother stops match making for her, and instead sets Will up. Jack must convince an INS agent (who he dated once) that he and Rosario are happily married.

When his work for Harlin takes up all his time, Will drops all his other legal clients; a decision that later comes up to bite. Meanwhile Grace tries to teach Karen how to live on a budget.

An unemployed Will agrees to serve as one of Jack's cater-waiters, until he learns that he'll be catering for American Bar Association. Grace discovers Karen's darkest secret: she once made a porn video.

Will and Grace are shocked to learn that Jack never told his mother he was gay and encourage him to open up to her at Thanksgiving. The evening brings a revelation for Jack as well: his father isn't who he thinks it is.

Grace looks to Will for representation when a hotshot lawyer doesn't pay her for a consulting assignment, but he ends up making Will a job offer. Meanwhile, Jack and Karen turn a training film set into an adult entertainment experience.

Tired of Rob and Ellen's low-rent taste in dining, Will and Grace start hanging with a pair of downtown hipsters they meet at a dim sum parlor. But as the new pals paint the town, Rob and Ellen see red when they catch their best friends lying to avoid plans to dine at their favorite eatery: a coupon-crazy Italian chain in Secaucus. Meanwhile, Jack's inner child gets a little pick-me-up when he joins Karen at a PTA meeting at her stepchild's school.

Will's new boss gives him an ultimatum - he has until Friday to bring in a major new client to the firm or lose his job.

Grace is excited to meet Will's best friend from high school until she learns that the woman has made a request: to be implanted with Will's sperm. Now Grace has to confront Will about Will being her "backup."

Erotic dreams about Grace send Will to a therapist, who seems more interested in Grace. Meanwhile Jack and Karen clash over her treatment of Rosario.

Will's ideal relationship with his loving father sours when his dad prepares to accept an award at his company's dinner banquet but tries to dissuade his son from attending because he's told everyone that Will is married to Grace. Meanwhile, Karen's private detective finds Jack's biological father.

Will and Jack appear on Today to protest NBC for cutting a gay kiss out of an eagerly-waited sitcom episode. Will is frustrated with Jack on how much he wanted to see that kiss and kisses him. Elsewhere, Grace confides in Karen about dumping her boyfriend.

Will reluctantly agrees to go on a blind date set up by his boss and, to his surprise, has a good time, but he's hurt by the other guy's post-date silence, so he lets Jack coach him on how be a good date. Meanwhile, Grace's frustration with her too-laid-back boyfriend mounts, and she takes dubious relationship advice from Karen.

Will thinks that he has another chance with Michael, his old boyfriend and Grace's new client. Meanwhile, Karen tries taking her "career" more seriously and asks Grace for greater responsibilities.

While on a blind date, Will finds out that Karen's husband Stan has had a heart attack and rushes to the hospital to be with the gang. Will, Jack, Grace, and Rosario all speculate on who Karen will turn to for her inevitable emotional breakdown. After all, who will pay the bills if Stan dies?

After winning a call-in radio contest for prized concert tickets, Grace vows to reciprocate and volunteers her time to charity.

When Ellen and Rob announce that they are getting married, Grace feels forced to reveal to Will that she once slept with Rob.

Despite their history, Grace spends a fun evening with Val only to have Will suspect her of stealing. Meanwhile Jack becomes attracted to the leader of Welcome Home-an organization for gays who have converted to going straight, so he acts straight to woo the man.

It's a scary glimpse into the future for Will and Grace when they visit their curmudgeonly retired college professor only to discover that he is a bitter old man that has a "Grace" of his own. Meanwhile, Karen must confront her most mortal enemy, the kitchen, when Stan requests a home-cooked meal for his birthday, and she looks to Jack and Ben to come to her rescue.

Grace discovers that one of Karen's friends is the notorious Helena Barnes, one of New York's most-celebrated interior designers, and her primary competition for a lucrative design job.

Unknown to Will, Grace has a romantic dalliance with his boss Ben, but when Will finds out, she makes him promise not to interfere.

In his noble attempt to help Jack and Grace with their love lives, Will's love life falls apart and he reaches his breaking point. Grace opts for menage a trois with Ben and Josh. She also tries to turn Jack into Will but he fights back.