<P> Aside from Will, Grace also has a close relationship with her assistant, Karen Walker, a rich, alcoholic socialite who does virtually no work . Karen is nevertheless useful to Grace, as she pays for her employer's health insurance, gives Grace holiday bonuses, and occasionally uses her society connections to help Grace get work . Otherwise, Karen spends her "work" hours drinking and belittling Grace . Karen routinely criticizes Grace's choices in fashion (usually by disdainfully asking, "Honey, what's this all about?") and men . Karen doesn't exactly withhold her judgments; in one episode, when Will calls Grace at work and Karen answers, she puts him on hold and says "Grace, the reason you're not in a relationship is on line one ." Nonetheless, Grace and Karen become close friends over the years . Grace eventually learns to look past Karen's faults, and Karen occasionally does stop ridiculing her to reveal a softer, more caring side . In one episode, Grace stands up to Milo (played by Andy García) who refuses to go on a second date with Karen, who was going through a divorce with her husband Stan and was very vulnerable at the time . In another instance, Karen turns down Grace's proposal for a business loan to protect Grace, who didn't really have a strong business plan . </P> <P> Grace also has a close bond with Will's other best friend, Jack McFarland . Early in the series, Jack and Grace dislike each other, seeing each other as a rival for Will's affections . However, after they spend time together while Will is in the Cayman Islands between Seasons two and three, they develop a closer friendship . They still antagonize one another, however, often leading to Grace striking Jack in some manner . </P> <P> Grace has a string of boyfriends throughout the series, many played by guest stars such as Woody Harrelson and Gregory Hines . Grace marries the Jewish doctor Leo Markus, played by Harry Connick, Jr., on November 21, 2002, but the marriage ends when he has a one - night stand with a doctor from the Red Cross while working in Cambodia with Doctors Without Borders . In season 8, the two reunite briefly during a flight to London when they coincidentally met on the plane . Their mile high tryst leads to Grace getting pregnant, but she doesn't tell Leo because he is engaged to another woman . However, in the series finale, she and Leo remarry and raise the baby, a girl named Laila, together . Laila is born in Rome, where Leo is working at a hospital as a researcher . After one year in Rome the family moves back to New York, to their apartment in Brooklyn . Laila goes on to attend college and there meets Will and Vince's son, Ben . Laila and Ben are living in dorm rooms opposite each other's while at college; the same scenario that Will and Grace found themselves in while they attended college . Ben and Laila marry soon afterward . </P> <P> When the series was revived in 2017, the events of the season finale - in which Grace gives birth to Leo's child and drifts apart from Will - are effectively retconned as one of Karen's alcohol - induced hallucinations . In this continuity, Grace has recently got divorced from Leo, has never had children, and has moved back in with Will while she recovers from the divorce . When Leo reappears sometime later, it is revealed that the marriage ended because of Grace's close friendship with Will as well as her inability to trust Leo not to cheat on her again . Despite the couple trying months of therapy and taking up golf together, they couldn't make it work and Grace, unable to forgive Leo, turned to Will for comfort . </P>

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