Former Bears’ QB Jay Cutler’s Cheating Rumors With Ex-Wife Kristin Cavallari’s Friend Kelly Henderson Derailed Their Marriage

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Kristin Cavallari and Jay Cutler started with nothing but went on to build a beautiful family. However, Cutler’s potential cheating with Kelly Henderson ended their marriage.

Jay Cutler is the former NFL quarterback with scandalous affairs wrapping around his relationship and marriage.

The Chicago Bears athlete had quite a highlighted relationship timeline with television personality Kristin Cavallari.

The former couple had known each other for more than a decade, and their marriage lasted for 7 years.

Jay and Kristin married in 2013, after a year or so of non-serious meetings and dating. However, they later connected well and tied the knot.

Their marriage formally ended in 2020, but the post-marriage drama that hiked up later never settled.

Jay Cutler and Kristin Cavallari Welcomed Three Kids Amid Their Brutal Claims Of Toxicity And Struggles With Their Relationship!

According to the report, Jay Cutler and his ex-wife, Kristin Cavallari, had a less-than-pleasant first interaction.

The lady later revealed that the QB was interested in dating her first when she wasn’t interested at all.

Speaking in an interview, she mentioned that Culter wanted her to fly out to Chicago and take her out. However, Kristin didn’t want a boyfriend, so she passed on it.

After a year, in 2010, they got a chance to have an encounter at a preseason football game, after which they began dating seriously.

According to Kristin’s book, she thought he was really cute and started flying to Chicago every few weeks for a date.

By April 2011, Jay proposed to her on a romantic getaway in Mexico, however, they called off their engagement months later.

Insider reports suggest that the former Bear dumped the model and broke her heart. While she was planning for a wedding, the athlete was planning something else.

Jay Cutler Ex Wife
Jay Cutler and his ex-wife, Kristin, started dating shortly after they met at a basketball event in 2010. (Source: Vanity Fair)

After months of breaking off, sources reported they were already working things out. Though they weren’t official again, the couple were repairing their love.

And around October 2011, everything seemed great, and Kristin made it official through a sweet Twitter post.

She wrote:

This time its official..Jay and I are engaged again:)

After announcing the child in January 2012, they welcomed Camden Jack Cutler into the world on August 8.

With a growing son as their ring bearer, Jay and Kristin got married on June 7, 2013, in a beautiful ceremony.

Within a few months of the wedding, the pair announced another baby. Cavallari revealed the birth of her second son, Jaxon Wyatt Cutler, through an Instagram post.

Likewise, on November 23, 2015, they again welcomed the fifth member of the family, their youngest child, Saylor James.

Kristin Cavallari and Jay celebrated their anniversary in 2016, and within three years, they had already become a family of five.

Fast forward to 2020, after the lady publicly said her husband is her constant, suddenly they decided to divorce.

People found it very unusual for the lovely couple to split, but some pointed out that Jay cheated on her in the last few years.

The Former Couple, Jay and Kristin Tried To Rekindle Marriage With Dates, But Couldn’t Make It Work

Though the couple ended their decade-long relationship in 2020, it wasn’t without drama and shocking revelations.

The couple cited ‘irreconcilable differences’ as the reason for divorce. But people always thought it to be due to previous dating allegations and rumor.

However, during the premiere of Very Cavallari, Cavallari addressed rumors that Cutler was cheating on her with Kelly Henderson.

The rumors and faceoff caused the fallout of her friendship with Kelly, underlying tensions within their marriage.

Kristin and Jay even reached a joint custody agreement with each spending 182.5 days a year with all three kids.

Shortly after filing for divorce, sources located them together, spending time together, discussing re-dating.

Despite their trial, the lovely pair never got things on better terms and remained connected just for co-parenting.

Both of them moved on, Jay Culter with Samantha Robertson and his ex-wife with Mark Estes in February 2024.

Kristina and Mark remained together just for seven months and sources believe that they split in September.

In Case You Didn’t Know

  • Cutler had always been a Chicago Bears fan since his youth and later went on to represent them.
  • He played himself in an episode of the comedy show The Legend.
  • The QB is one of the founders of Outsider, a digital media lifestyle company.
Ujjwal Parajuli
Ujjwal Parajuli
Ujjwal Parajuli is a seasoned writer with extensive experience in the field, having dedicated many years to honing his craft. His work spans a variety of genres, demonstrating his versatility and depth as a writer. Alongside his passion for storytelling, Ujjwal has a keen interest in sports, particularly football, American football, baseball, and several other athletic pursuits.

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