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Britney Spears’ Romantic History: From Dating Justin Timberlake To Surprise Wedding With Sam Asghari

Shortly after being linked to Colin, Britney hooked up with one of her backup dancers, Columbus Short. The following year, Columbus opened up about the hookup in an interview with Star magazine, and admitted that it led to the demise of his marriage (his wife was pregnant with their first child at the time). Columbus’ employment with Britney was terminated afterward, as well.

Britney Spears, 40, Is Expecting Her First Baby With Fiancé Sam Asghari: Here Are All The Details

The couple started dating after meeting in 2016 on the set of her “Slumber Party” music video with Tinashe, per ELLE. They made things public in 2017 and have been going strong ever since.

Five years later, they’re not only engaged but are also prepping for parenthood.

The Pop Princess, 40, and her husband-to-be have received a tremendous amount of support from fellow celebrities and fans who have been by her side during the fight to end her conservatorship last year, which ended officially on November 14.

Here’s everything to know so far about Britney’s pregnancy and due date:

How did they announce the pregnancy?

Both parents-to-be took to social media for the big reveal with separate Instagram posts. Britney was the first to break the news saying, “I lost so much weight to go on my Maui trip only to gain it back 🤷🏼‍♀️🤷🏼‍♀️🤷🏼‍♀️ … I thought ‘Geez … what happened to my stomach . ‘ My husband said, ‘No you’re food pregnant silly 🤪 . ‘ So I got a pregnancy test … and uhhhhh well … I am having a baby. ” She then went on to reveal more about how she plans to approach pregnancy this time around, noting that she’s dealt with perinatal depression in the past.

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Sam also posted a sweet caption on his page the next day saying, “Marriage and kids are a natural part of a strong relationship filled with love and respect. Fatherhood is something I have always looked forward to and I don’t take lightly. It is the most important job I will ever do.🙏”

What’s the sex of the baby?

While the sex of the baby has not been revealed, fans have their own theories based on Britney’s announcement post. In case you haven’t seen it yet, the photo features pink flowers laid next to a pink teacup and saucer, leaving fans to believe there might be a baby girl on the way.

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Britney has wanted kids with Sam for a while.

During one of the court hearings to end her 13-year conservatorship, Britney hinted during her testimony that she was ready to start a family with Sam.

“I want to be able to get married and have a baby,” Spears told the judge, per Billboard. “I was told right now in the conservatorship, I’m not able to get married or have a baby. I have an IUD inside of myself right now so I don’t get pregnant. I wanted to take the IUD out so I could start trying to have another baby. But this so-called team won’t let me go to the doctor to take it out because they don’t want me to have any more children.”

Since her father stepped down as her conservator during the summer of 2021, Britney has been taking steps to live the life she wanted with Sam. The couple got engaged last September after five years of dating, and are planning to tie the knot soon.

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She already has two kids with her ex-husband Kevin Federline.

While this is Sam’s first child, Britney already has two kids with her ex-husband Kevin Federline. She had her first son, Sean Preston Federline, 16, in 2005 and her second son Jayden James Federline, 15, a year later. Let’s hope these two are ready to take on big brother duties!

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So when is the baby due?

The baby’s due date is still a mystery, but Britney did say she was initially feeling nausea while on her trip to Maui.

“The only thing that is similar to this feeling is when I was pregnant 🤰… it’s the nausea 🤢,” she captioned an Instagram post where she sunned herself in a yellow bikini.

That was back in January, so if she waited until the end of her first trimester to announce the pregnancy, she could be giving birth sometime this fall.

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Sabrina is an editorial assistant for Women’s Health. When she’s not writing, you can find her running, training in mixed martial arts, or reading.

Britney Spears’ Romantic History: From Dating Justin Timberlake To Surprise Wedding With Sam Asghari

Now that Britney Spears has married Sam Asghari, it’s time to do a deeper dive into the pop star’s love life over the course of her career.

Reading Time: 6 minutes
June 9, 2022 8:55PM EDT
Image Credit: MEGA

Britney Spears has been in the spotlight for more than 20 years and on June 9, 2022, the iconic pop star walked down the aisle with longtime boyfriend Sam Asghari. But before Sam came along, Britney got married twice and engaged three times. She also birthed two sons, and had a high-profile romance with Justin Timberlake. Want to know more? Take a look at this breakdown of her romantic history.

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Justin Timberlake

Britney Spears and Justin Timberlake at an event together. (AP)

Britney and Justin Timberlake were the ultimate pop music couple when they dated from early 1999 until 2002. At the time, she was at the height of her early career, while he was at the peak of his boy band days in NSYNC. They were together for more than three years when things ended quite abruptly. After the split, Justin went on to release his first solo song, “Cry Me A River,” which he eventually admitted was about his split from Britney. Although they grew apart over the years, they both complimented each other on social media in 2020.

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Wade Robson

Britney Spears and Wade Robson on separate occasions. (AP Images)

Britney dated choreographer Wade Robson for about a year after her split from Justin. However, there have been widespread rumors that she began hooking up with Wade before ending things with Justin. Britney has never confirmed whether or not there is any validity to this speculation. Robson is one of the men who has accused Michael Jackson of sexual abuse, and his claims were the subject of the 2019 documentary, Leaving Neverland.

Colin Farrell

Colin Farrell wraps his arm around Britney Spears. (AP Images)

Britney and Colin Farrell sparked major romance rumors when they attended the premiere of The Recruit together in 2003. Later on, they were also spotted making out on his hotel room balcony! However, Colin denied that the two were ever anything serious, and insisted that they were just “having fun.”

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  • Britney Spears Stuns On The Beach In A Sexy Red Bikini — Plus More Of Her Hottest Pics
  • Britney Spears’ Boyfriend Sam Asghari Professes His ‘Love’ For Her In Goofy Bedroom Video

Columbus Short

Britney Spears dances with Columbus Short onstage.

Shortly after being linked to Colin, Britney hooked up with one of her backup dancers, Columbus Short. The following year, Columbus opened up about the hookup in an interview with Star magazine, and admitted that it led to the demise of his marriage (his wife was pregnant with their first child at the time). Columbus’ employment with Britney was terminated afterward, as well.

Jason Alexander

Britney Spears and Jason Alexander on separate occasions. (SplashNews)

In 2004, Britney shocked everyone when she married her childhood friend, Jason Alexander, at the Little White Wedding Chapel in Las Vegas. However, in one of the most short-lived celebrity marriages of all-time, the pair annulled their union after just 55 hours of wedded bliss. Britney filed a petition with the court, which stated that she “lacked understanding of her actions” at the time of the nuptials.

In a shocking turn of events, Jason was arrested on June 9 after he tried to crash Britney’s wedding to Sam. In a video on his Instagram Live, Jason filmed himself trying to sneak into the pop star’s wedding in Thousand Oaks, CA as police arrested him.

Kevin Federline

Britney Spears and Kevin Federline out and about together. (SplashNews)

That same year, Britney met backup dancer, Kevin Federline. Just three months after they met, the two were engaged, and they tied the knot in September 2004 (although the nuptials were not legalized until a few weeks later). At the time all of this was happening, Kevin’s ex, Shar Jackson, was pregnant with his second child. Britney and Kevin wound up having two sons of their own: Sean Preston was born in Sept. 2005, followed by Jayden James in 2006. As Britney began dealing with some issues with her mental health, her relationship with Kevin fizzled out, and they split in 2006. The divorce was finalized in July 2007.

J.R. Rotem

Britney Spears out and about with J.R. Rotem. (SplashNews)

Following her divorce from Kevin, Britney didn’t take long to get back on the dating scene. She briefly dated music producer J.R. Rotem in 2007, although there was some speculation that their relationship potentially began while she was still with Kevin. Again, this has not been confirmed by either party.

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Adnan Ghalib

Britney Spears on an escalator with Adnan Ghalib.

Britney shocked her friends, family and fans when she got together with a paparazzo at the end of 2007. She briefly dated photographer, Adnan Ghalib, despite the fact that she was being hounded by paparazzi for months. Although the relationship was short-lived, Adnan re-entered Britney’s life in 2012 when he testified in Sam Lutfi’s case against the singer (Sam sued Britney for unpaid fees and accused her father, Jamie, of punching him).

Jason Trawick

Britney Spears at an event with Jason Trawick. (SplashNews)

After these flings, Britney got into another long term relationship beginning in 2009, when she started dating her manager, Jason Trawick. The pair’s relationship was confirmed in 2010, and in December 2011, the two got engaged. Jason even became a co-conservator for Britney and obtained legal control of the singer. Unfortunately, the relationship eventually fizzled out, and Britney and Jason split at the beginning of 2013. At that time, he was removed as her conservator.

David Lucado

Britney Spears holds hands with David Lucado. (SplashNews)

Following the end of her engagement to Jason, Britney began dating a lawyer, David Lucado, in 2013. However, the romance lasted just one year, and by 2014, the two had broken up. At the time, it was reported that Britney ended the relationship because she caught David kissing another woman, but those rumors have not been confirmed.

Charlie Ebersol

Britney Spears and Charlie Ebersol cozy up on the red carpet. (SplashNews)

Brit’s next relationship was with Charlie Ebersol, who works as a producer and is the son of Saturday Night Live‘s co-creator, Dick Ebersol. They got together in 2014 and even made public appearances on red carpets together. However, the relationship ended in 2015.

Sam Asghari

Britney Spears and Sam Asghari on the red carpet. (MEGA)

Britney met her current husband, Sam Asghari, on the set of her music video for “Slumber Party” in 2016. Despite an age difference of more than ten years, the two hit it off and exchanged numbers after the shoot. They started seeing each other afterward, and went Instagram official in January 2017. Ever since, Sam has been a rock for Britney — he was a solid support system when she sought out mental health resources in 2019.

More recently, Sam spoke out about his relationship with Britney, and the pop star’s father, Jamie Spears‘, involvement in her conservatorship — instituted roughly 12 years ago. “Now it’s important for people to understand that I have zero respect for someone trying to control our relationship and constantly throwing obstacles in our way,” Sam shared on his Instagram Story. “In my opinion, Jamie [Spears] is a total d*ck.” The statement came just days following the premiere of The New York Times‘ documentary Framing Britney Spears premiered on FX and was later viewed by fans on Hulu.

After Sam proposed to Britney in September 2021, the pair got hitched in a surprise wedding on June 9, 2022! In front of a small group of friends — including Drew Barrymore, Paris Hilton and Selena Gomez — the couple said ‘I do’ with Sam getting silly at the reception afterwards by wearing Britney’s veil. He also sported a custom T-shirt reading ‘BRITNEY & SAM’ on the front as the couple left their special event in a Rolls Royce.

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