Schwimmer had the hots for singer Natalie Imbruglia in the ‘90s. The “Torn” singer confirmed they were dating during a May 2015 interview with Red magazine. “That was a happy relationship,” she said.

Imbruglia also remembered what it was like to date Schwimmer when he worked on Friends and had a crush on Jennifer Aniston. "I do remember being on the set and I remember everyone being lovely and really, really nice,” she said on TODAY in June 2021. “I wasn't paying attention to whether [Schwimmer and Aniston] were giving each other, you know, little looks over my shoulder. I don't know if that was happening.” But luckily, she’s over it. “I'm OK with whatever happened back then,” she added. “It was a long time ago.”

In a March 2020 appearance on Danny Pellegrino’s Everything Iconic podcast, Brandi Glanville revealed she once dated Schwimmer and his Friends co-star Matt LeBlanc, though it’s unclear exactly when the rumored romances happened. The Real Housewives of Beverly Hills star said things didn’t go far with Schwimmer because she had an issue with him wearing makeup all the time. “He wore concealer out during the day and it really annoyed me,” she said. “I understand you’re on set, you’re used to wearing makeup, but I wasn’t used to a man wearing makeup. In the moment, it bothered me.”

Glanville also claimed that Schwimmer called her a “bigger girl” even though she weighed roughly “109 pounds” at the time. When Page Six asked the actor about his relationship with Glanville, he simply called the story “false,” so take from that what you will.

After meeting on the set of the 1998 movie Kissing a Fool, Schwimmer proposed to actor Mili Avital in March 2001. But near the end of that year, the two lovebirds called off their wedding and split up for good. Fortunately, the parting seemed to be on good terms. "We're still great friends,” he told ABC News in October 2001. “But I guess I'm spending too much time on work these days. But it was definitely a mutual and amicable parting."

But even by May 2005, Schwimmer was still mourning the end of the romance. “A lot of men today don't have the courage to fall in love. The only one I really fell for was Mili,” he told the Irish Examiner. “I don't think I even recognized it until it was too late. In some ways, I'm haunted by that. I don't know if one can ever fall again as far as one does the first time."

Schwimmer started dating Coyote Ugly star Carla Alapont in August 2002. Although he really liked her, the duo ended up going their separate ways in November 2003. When Gear magazine asked Schwimmer what was going on in his love life, he told them that he has a bad habit of putting his relationships last and his career first. “I could have a wife and family by now,” he admitted. “My mother asks me every other week, ‘Have you found a nice girlfriend?’ Now I have started to ask myself the same question.”

Schwimmer continued, “I haven’t even come close to engagement. There was one point when I thought I was getting close with Carla, but again I had my priorities in the wrong place. I put work before my relationship, which I always seem to do.”

Schwimmer was romantically linked to Unisex Salon singer Gina Lee in 2004. The pair reportedly got together after Lee broke up with her bandmate and ex-fiancé Kenyon Phillips and Schwimmer called it quits with Alapont, per the Irish Examiner. However, their alleged romance didn’t last for long because Lee’s friends reportedly said she only dated Schwimmer as her “rebound” guy, and when it all came down to it, they had “little in common.”

Schwimmer and S Club 7 member Tina Barrett were rumored to be dating in 2004. After meeting at the Glamour Awards, they reportedly jetted off to Spain for a vacation in June. However, that appeared to be it for their alleged romance, because that was the last time they were spotted out together.

In 2007, Schwimmer met his soon-to-be-wife Zoë Buckman at a bar in London. At the time, Buckman was working as a server and she crossed paths with the actor when he was filming his movie and directional debut Run, Fatboy, Run.

In June 2010, the couple got married, and just about a year later in May 2011, they welcomed their beautiful daughter, Cleo Buckman Schwimmer. But after spending seven years together, the pair announced they were separating in 2017 when they released a joint statement to Us Weekly.

"It is with great love, respect, and friendship that we have decided to take some time apart while we determine the future of our relationship,” they said at the time. "Our priority is, of course, our daughter's happiness and wellbeing during this challenging time, and so we ask for your support and respect for our privacy as we continue to raise her together and navigate this new chapter for our family."

Schwimmer later opened up about his divorce during a January 2020 interview with The Guardian. While recalling his time with Buckman, the Intelligence actor said it was “heartbreaking” to see them fall apart. “You feel somewhat responsible and a sense of failure — and you grieve. I certainly didn’t get married with the idea that it wouldn’t last. I really believed it would,” he said.

Although the duo broke up, they continue to co-parent Cleo together. “Just making sure Cleo was going to be OK and feel supported and loved was quite painful for everyone, obviously, but I can say now that she feels really safe and happy,” Schwimmer said. “And all three of us try to do things together.”

Schwimmer was most recently linked to Katie Markowitz. A source reportedly claimed to Us Weekly that Schwimmer and Markowitz “met at a bar where he bought her a drink” and after that, the two went on “a few dates.” However, Markowitz reportedly told Us Weekly that she was never in a romantic relationship with the Friends alum.