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 2 and 3, they develop a closer friendship. They still antagonize one another, however, often leading to Grace striking Jack in some manner. Romantic relationships Grace has a string of boyfriends throughout the series, many played by guest stars such as Woody Harrelson and Gregory Hines. Grace marries Leo Markus (Harry Connick, Jr.), a Jewish doctor 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 living in Rome for a year, the family moves back to New York, to their apartment in Brooklyn. Laila (Maria Thayer) goes on to attend college and there meets Will and Vince's son, Ben (Ben Newmark). 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. 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 retconned as one of Karen's drug and alcohol-induced hallucinations. In this continuity, Grace has recently divorced 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 Grace did not trust Leo not to cheat on her again, and because she was closer to Will than to her own husband. Despite the couple trying months of therapy and taking up golf together, they could not make it work and Grace, unable to forgive Leo, turned to Will for comfort. In season 10, Grace