Her love life is a mystery. His love life is a mystery. Jennifer Coolidge and Chris Kattan may
have been the perfect comedic duo in the late 90s. Sadly, they broke up before their fans
even learned of their romance. And the reason for that is rather devastating.Today, we’re
looking at their relationship, their downfall and the romantic history the actors had onwards.
If this is the first you’ve heard of the comedic actors dating, you’re not alone. Jennifer Coolidge
especially is fiercely protective of her personal life, with very little information about any
past or current partners available. Yet Chris and Jennifer make perfect sense as a couple.
Both are known for their larger-than-life personalities and their hilarious character
sketches. But the possible reason behind the two actor’ breakup is anything but funny.
Rumors of Coolidge and Kattan’s romance first started circulating in the early 2000s.
Then Chris confirmed the two were involved when he published his 2019 memoir, Baby Don’t Hurt Me.
In addition to behind-the-scenes stories and hot gossip from his Saturday Night Live days,
he also admits to falling for Coolidge pretty hard.
“Jennifer Coolidge was a tall, messy, sexy, tough, charmingly crass Boston native bombshell. But
this didn’t stop me from crushing on her,” he gushed, describing the blonde beauty.
The two soon embarked on a steamy romance. They were even thought to be married.
Yep! You heard that correctly. Rumors were circulating at the time that the couple exchanged
vows in an intimate wedding ceremony in front of their closest friends and family. However,
except that the theory was widely disseminated, there is little proof this was the case.
Although Chris doesn’t go into great detail about their relationship in his memoir, it
sounds like it hit a rough patch towards the end. In what came to be one of the more infamous
sections of his memoir, as reported by AV Club, Kattan detailed how a request from
someone in a position of power threatened to bring the end to their relationship.
In his memoir, he describes their status as “deteriorating” when he was filming A Night
at the Roxbury, a movie based on his famous SNL sketch with Will Ferrell . Interestingly — and
alarmingly — it appears that this film might be what eventually led to his split from Coolidge.
In a shocking twist, Chris revealed that SNL’s creator and producer Lorne Michaels
pressured him into starting a physical relationship with
Amy Heckerling , who was at that point attached to direct.
Stories about Lorne Michaels’ intimidating influence and prickly personality
have been around as long as SNL has been on the air. Still, an excerpt from the actor’s
memoir paints a particularly damning picture of the powerful comedy producer.
“Paramount would only do the movie if Amy signed on as director … If I wanted to
make sure the movie happened, I had to keep Amy happy,” Kattan writes, describing how
Michaels was furious with him the day after he initially refused Heckerling’s advances.
“Chris, I’m not saying you have to fuck her, but it wouldn’t hurt,” Lorne said. Chris, then only
27 years old, describes the inner turmoil he felt about being told to sleep with a woman who was,
at that time, an influential creative figure in Hollywood and ostensibly his boss.
Though initially reluctant, he eventually had a consensual encounter with Amy.
The actor decided not to tell anyone about the incident, which he claims put
an untenable strain on his already fraying relationship with then-girlfriend Jennifer
Coolidge and his friendship with Will Ferrell. Though he maintains the encounter was consensual,
the familiar power dynamics are present. “I was attracted to Amy,” Kattan writes.
“But at the same time, very afraid of the power she and Lorne wielded over my career.”
In the end, Amy Heckerling signed on as a producer,
and the film turned out to be a critical bomb. Lorne and Heckerling have never publicly
commented on the story. As for Coolidge, she continues to keep her private life private.
Mollie Heckerling, Amy’s daughter, took to Twitter to share her account of Kattan’s
relationship with her mother. While her account differs significantly from Kattan’s, she ended
by saying she would be “VERY interested to hear what Lorne Michaels has to say about all of this.”
Chris Kattan has had a string of high-profile romances onwards. In 1999, he began dating
Jennifer Gimenez , an American model and actress. The relationship turned out to be a bit of a fling
as the couple reportedly didn’t date long. Kattan was also romantically linked to his
fellow Saturday Night Live alum Maya Rudolph. The actors were reported to have a brief
fling in October 2001 before Chris met model Sunshine Tutt at a birthday party in 2005.
The couple began dating, and on Christmas Eve 2006, Kattan popped the question.
The lovebirds tied the knot two years later in Oakhurst, California.
Although they dated for a few years before walking down the aisle, their marriage was short-lived.
The pair announced their split just eight weeks after their wedding day,
revealing that they decided to separate. The duo cited “irreconcilable differences”
as the reason for their split and were officially granted a divorce in February 2009.
TMZ reported at the time that Tutt left the marriage with a “low six-figure sum.”
Tutt’s lawyer said that the model would use the money to “rebuild her life.”
Most recently, Chris was linked to model Cheyenne Gordon. The two went public with their romance in
late 2019 and even made an appearance together at the Elton John AIDS Foundation Academy
Awards Viewing Party. However, since then, Kattan has stayed quiet about his love life.
As for Coolidge, theories about her love life have circulated for years but have never been
confirmed. She hilariously revealed to Kelly Clarkson that she once pretended
to be a twin so she could date two men who lived in the same area at the same time.
“Quite a few years back, I did come to Kauai. When you come and you’re on vacation alone,
you can kind of create anything you want. I ended up meeting these two guys that were best friends,
and I liked them both. And so, I told them that I had an identical twin. And
I dated both guys — for two weeks.” After Kelly Clarkson threw her head
back in laughter and called the sneaky plan “exhausting,” Jennifer said that
she only got away with it because of her age. “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,” she said. “You know,
when you’re younger, you can just about get away with anything.”
Clarkson then turned to her other guest, Peter Krause , and asked whether he thought that he
“would fall” for the Promising Young Woman star’s scheme if he were in one of the men’s shoes.
“Well, I’d have to find out which twin I liked best,” the Six Feet Under alum joked.
“So, at least twice.” A private person, Jennifer
isn’t averse to dropping small clues about her personal life in interviews with the media.
In 2013, she told the Guardian that American Pie might have subtly seeped into her romantic life
as she took up a newly found interest in dating younger men after working on the movie.
“I really dated younger men for the next 10, 15 years,” she said.
Jennifer further revealed that she was dating someone younger than her,
but she didn’t want to reveal his identity as he might be unable to handle it.
She also touched on the topic during an appearance on Watch What Happens Live With
Andy Cohen in 2020. “I have to say the movie has helped me out in a lot of ways,” she joked.
“Even as ... there’s always someone who has seen that movie lately, and so then you get a
whole new group of young guys. I’m single, so I’m really using it to my advantage.”
Overall, the legendary actress doesn’t seem to be too intent on pursuing public relationships.
Instead, she frequently makes red-carpet appearances by herself
and mostly posts about work on social media.
Over the years, numerous fan theories have emerged about fellow comedians she may have married
and stars she could have dated. One (unproven) theory holds that Jennifer
married a man named Tom Mahoney a while ago. Others believe they are (or were) dating.
In the past, there were rumors that Coolidge would get married soon. In her Instagram post,
Jennifer was spotted with a ring on her ring finger, which looked like a wedding ring.
However, she didn’t make any announcement, which drove people to conclude that the ring
might be fancy, but it’s not a wedding ring. The actress is fascinated by liars and con men:
The last time she had a Halloween party, in 2019, the costume prompt was to dress
up as your favorite narcissist — or their victim. These themes may or may
not be inspired by personal experience. Either way, Coolidge stays in the game.
She doesn’t necessarily want to be dating some rich guy,
but the more salt-of-the-earth, non-Hollywood men she’s been with can be insecure about her success.
“Their perception of your life is so much bigger and better than what it really is,”
she says. “They somehow project a bunch of shit onto you, that you’re
usurping them or doing something to them.” In her Vulture interview, Jennifer confirmed
she is single, but she’s a romantic at heart. “I don’t want this to be the end of my life and
my romance and all that,” she said. “But I don’t know how people do it anymore.
Sometimes I feel like you got this good little thing going once in a while with somebody.
You get too much permission to, you know, be you. The thing dissolves pretty quick.’”
For now, she stays focused on her career, recently telling Us Weekly that she was
hoping to reprise her role as Paulette in the upcoming Legally Blonde film.
And that’s all we have for you today, Juicers!
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