Dr. Marvin "Leo" Markus, played by Harry Connick, Jr.. A Southern-born Jewish doctor who met Grace when she ran into a lamppost, Leo soon charmed even Will, and ended up proposing to — and marrying — Grace. A supporter of Doctors Without Borders, Leo was rarely in the country and had a one-night stand in Cambodia that led to the demise of their marriage. They reunited for one brief fling on a plane to London in season 8, which resulted in Grace becoming pregnant. Although Grace at first chose not to tell him about the pregnancy, he ultimately proposed to her. In the series finale, it was shown that Grace and Leo remained married, raising their daughter Lyla, who ultimately married Will's son Ben.

Nathan, played by Woody Harrelson. Grace's neighbor in season 3 who became her boyfriend. They appeared to be a good match, but early in Season 4 he abruptly proposed to her during sex and she became distraught at the unromantic nature of his proposal, and forced him to take it back and ask again in a more romantic way. For several days they were awkward around each other, and fearing that their relationship was over, Grace proposed to Nathan, who reluctantly refused, and broke up with her.

Ben Doucette, played by Gregory Hines. Introduced in mid-season 2, Grace sued him after he violated her contract of employment and fired her without reimbursment for expenses she incurred while decorating his house. Although at first he played Grace and Will, who was representing her, he eventually gave her the money voluntarily and hired Will at his renowned law firm. Grace and he disliked each other for the rest of the season, until the season finale when Ben showed her his more humane face when Will invited him to dine with them. They then started a happy semi-monogomous relationship that lasted for roughly six months, until they broke up early in Season 3 when they realized that they were not in love.

Josh, played by Corey Parker. A sweet, romantic New Age-y man whom Grace dates briefly in season 2 (2000).

Nick, played by Edward Burns. A greeting-card writer who falls for Grace when he meets her one Valentine's Day.

Tom Cassidy, played by Eric Stoltz. An old friend of Grace's, now married, with whom she reunited briefly.

Danny, played by Tom Verica, Grace's long-term boyfriend from roughly 1995-1998, whom she nearly married in the Pilot. She realized after Will advised her against the marriage, that Danny was too immature for her, and practically left him at the alter. They reunited at the end of season 1, much to Will's dismay. Yet again Grace decided that she did not love him, and after roughly a week (one episode) Grace broke up with him offscreen.

Mark, placed by Ken Marino is another of Grace's partner in Season 3, Three's a Crowd, Six is a Freakshow. She dumped him because he has 6 toes, although the actual 6th toe was not seen in the episode