Will & Grace - Season 1 (1998)

When Grace decorates Harlin's apartment, she gets carried away with a cowboy theme. Will is both shocked and embarrassed by the cowboy chic and makes an even greater mess of the situation. Meanwhile, Jack decides to embark on a singing career - with a little help from Karen.

Will and Grace plan to spend a serious Halloween together watching Ingmar Bergman movies at home - until Harlin drops off his over-eager kids at their place when he's called away on business. Meanwhile, Jack convinces Karen to accompany him to the downtown parade where she becomes an honorary drag queen.

When Jack reveals to Grace that Will once had an affair with a "client," she becomes paranoid that Will is keeping secrets from her. Her suspicions continue to grow when Will meets Karen for a discreet meeting to discuss her legal problems and will only tell Grace he's meeting with a client.

Grace blames her relationship with Will as the reason for her lack of interest in dating and decides they can no longer have fun together. Meanwhile, Jack enlists Will's help when the IRS catches up with him.

Grace has the opportunity to buy the studio that serves as her office space and turns to Will for first-time buyer advice. However, Will's negotiating tactics lead Grace to believe that Will thinks she is incapable of closing the deal and she sets out to prove him wrong. Meanwhile, Jack wants to become a massage therapist and practices his technique on a delighted Karen.

Will balks at first when Grace decides to adopt a dog, but the winsome pooch soon becomes his obsession, until Grace coaxes him to let Jack and Karen puppy-sit, with surprising results.

Will and Grace become hooked on a real-life soap opera unfolding in their neighbors' apartment when they begin eavesdropping through the new heating vent in their floor. As Will and Grace live vicariously through the marital infidelities of the downstairs couple, Jack feels neglected and enlists Karen's help in staging a play that drives the message home to his two best friends.

It's Will's birthday and all he wants is a nice, quiet dinner with his two best friends, Grace and Jack. When Jack and Grace discover they share a passion for figure skating, they surprise Will with tickets for Champions on Ice and Karen reluctantly joins the special evening.

Will hires a cleaning lady to "rescue" his designing roommate Grace from the creative chaos that litters their apartment, and while preparing for an annual decorators' contest, Grace develops a dependency on her maid and can't create without her. Meanwhile, Jack poses as an attorney in Will's office to impress an attractive guy he hopes to date.

Grace's visiting mom, Bobbi Adler, a would-be star whose propensity for breaking out into show tunes and impressions dismays her daughter - and delights Will, Jack and Karen - wreaks havoc by suggesting Will and Grace wed, despite their sexual differences. When Will winces at the fantasy of committing to anyone who needs to be the star of a relationship, Grace realizes she's more of a chip off the old block than she imagined.

A "surprise" birthday party for Jack astounds Will when his estranged older brother Sam turns up at the fête at Grace's invitation. Not only do sparks fly between the brothers, but electricity of a different sort crackles between Grace and Sam. Meanwhile, Karen flashes her platinum card for Jack as the pair shop until they drop at a boutique where the snooty salesmen previously had snubbed Jack.

A wary Grace tells Will of her romance with his brother, Sam, and unleashes an avalanche of resentment.

Stunned to find they have a 'date' with the same guy, Will and Grace compete for the affections of a handsome, charming new neighbor at dinner, and even Jack's 'gaydar' can't pick up his preference.

The gang retreats to a cabin in Vermont for the weekend, where Grace rekindles romance with an old flame and tries to hide the fling from Will, who's pining on the eve of his would-be anniversary.

Will finds a 'substitute Grace' in Val, a new neighbor who is available for plans with Will while Grace is consumed with work. As Will and Val continue to spend more time together,

Will learns a lesson about prejudice from Jack; Karen tells Grace about her rocky marriage.

A successful publicist hires Grace to decorate his office with the condition that Will dates him.

Grace tones down her competitiveness during game playing, while Will's focus changes to winning; Karen saves a workman.

Will and Grace rethink their living arrangement; Jack agrees to marry Karen's maid.