![Jennifer Coolidge reveals extreme measure she went to so she could date two men at once](https://images.ladbible.com/resize?type=webp&quality=70&width=3840&fit=contain&gravity=auto&url=https://images.ladbiblegroup.com/v3/assets/blt8bbf16c2d7a209e5/bltd433be31d96a2d90/66c5f7890cf571d7d4d0934a/jennifer-coolidge-dating-history.png)
While the idea of juggling two potential love interests - both equally obsessed with you - might sound like some kind of fantasy, according to Jennifer Coolidge, it's actually pretty tricky business.
Thankfully, however, she was able to make it work until she decided which lover to invest all her time into - though she says it definitely wasn't easy.
Despite never having tied the knot, the Legally Blonde actress has enjoyed several relationships throughout the duration of her time in the spotlight.
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![Jennifer previously dated comedian Chris Kattan. (John M. Heller/Getty Images)](https://images.ladbible.com/resize?type=webp&quality=70&width=3840&fit=contain&gravity=auto&url=https://images.ladbiblegroup.com/v3/assets/blt8bbf16c2d7a209e5/blt763cf13fd395f971/66c5f057562481257746e345/Screenshot_2024-08-21_at_14.48.05.png)
The now 62-year-old most famously dated comedian Chris Kattan back in the late 90s, though their romance reportedly ended after he became overwhelmed by the pressure of his Saturday Night Live fame, as per his 2019 memoir.
In recent years, however, the actress has kept a pretty low profile when it comes to her love life.
Until recently, that is, after she told gal pal Kelly Clarkson that she'd once two-timed two men she met on holiday in Hawaii.
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Jennifer began her admission by firstly explaining that she frequently visits the US state - where she claimed to have enjoyed several 'crazy experiences' - being one of her close friends owns a farm on the island of Maui.
"Quite a few years back, I did come to Hawaii and when you come and you're on vacation alone, you can kind of like create anything you want," she explained.
![The actress claimed she's a regular visitor to Hawaii. (Instagram/@jennifercoolidge)](https://images.ladbible.com/resize?type=webp&quality=70&width=3840&fit=contain&gravity=auto&url=https://images.ladbiblegroup.com/v3/assets/blt8bbf16c2d7a209e5/blt8a6571aa0d12e29e/66c5f49d1f94447cd444eaa7/Screenshot_2024-08-21_at_15.06.37.png)
"I ended up meeting these two guys that were best friends and I liked them both."
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Asked how she was able to balance romances with both men at the same time, Jennifer claims she told the BFF duo that she has a sister.
"I told them that I had an identical twin and I dated both guys," she confessed. "For two weeks!"
Jennifer went on to tell Kelly that she actually found the process of secretly double-dating two men quite thrilling.
She confessed, however, that she's never been as adventurous as to do so nowadays.
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"That seems exhausting!" Kelly replied to her tale.
Jennifer then replied: "I don't know if I would have the guts to do that now but at the time it really was sort of a great decision. Because you know, when you're younger you can just about get away with anything."
![The actress has always remained pretty low-key about her love life. (Gilbert Flores/Variety via Getty Images)](https://images.ladbible.com/resize?type=webp&quality=70&width=3840&fit=contain&gravity=auto&url=https://images.ladbiblegroup.com/v3/assets/blt8bbf16c2d7a209e5/bltd8955e31b6e2d54e/66c5f464cba1dfa89b809518/GettyImages-1971224087.jpg)
Just last year, the American Pie actress claimed that dating is no longer on the forefront of her mind, and insisted she's happily single.
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Speaking to Time Magazine in April 2023, she opened up: "There was just like, a giant chunk of my life that was wasted on trying to get boyfriends who didn’t want me, instead of just, you know, taking care of business and, and working on my own thing.
"I think we have to really take care of ourselves and get our own thing going. And then if a guy comes in, it’s all great. Or if a guy doesn’t come in, it’s all great."
Topics: Celebrity, Sex and Relationships, US News, Jennifer Coolidge