Celebrity Couples Who Famously Broke Up With a Baby on the Way

First comes breakup, then comes…baby.

That’s at least how the timeline went for these famous pairings. Most recently, former football pro Ed Hartwell filed for divorce from his wife of less than seven months, The Cosby Show‘s Keshia Knight Pulliam, after announcing just days earlier that they were expecting their first child together. 

However, Hartwell and Pulliam are not the first to pull the plug on their romance before meeting their son or daughter. They join a long list of couples who have called it quits during a pregnancy. From quarterback Tom Brady and model Bridget Moynahan to Kevin Federline and Shar Jackson, famous duos from all arenas of Hollywood have surprisingly ended things before welcoming a new baby. 

Here’s a rundown of eight of those pairs who split before the stork arrived: 

1.Tom Brady and Bridget Moynahan

Long before #Deflategate or even his marriage to the highest paid model in the world, Brady was dating Natasha Bridget, an actress and model who rose to fame on Sex and the City. After a three-year relationship, the couple split in December 2006. However, two months later, Moynahan’s rep confirmed she was expecting her first baby by Brady. Six months later, she gave birth to John Edward Thomas Moynahan. By that point, Brady and Gisele Bündchen had already started dating. 

“It was a challenging thing because here I am, you know, thinking, I’m dating this guy, we met, and we started dating and everything is great and then this happens,” Bündchen said during an interview with CBS This Morning‘s Charlie Rose. “So, then I felt like I didn’t know what to do. It was kind of one of those moments of like, ‘Do I just run away?'” Instead, she stayed and they’ve been married for seven years. 

2. Kevin Federline and Shar Jackson

Years prior to Kevin and Britney: Chaotic, Federline was a dancer dating and later engaged to the Moesha actress. In late 2003, Jackson got pregnant with their second child. However, when Kevin met Britney at a club, sparks flew and by June 2004, the pop star and the backup dancer had famously wed.

Meanwhile, Jackson gave birth to Kaleb Michael Jackson Federline a month later. 

3. Christina Milian and The-Dream

This split was a bit of a puzzle for fans to put back together. The singer and rapper wed in Las Vegas in September 2009. Milian then gave birth to their first child, daughter Violet, in February 2010.  However, the couple back-peddaled when they later announced that they had already secretly split months earlier. 

“The couple reached this decision in late 2009, but decided to keep the news private in efforts to protect their baby daughter, Violet. They ask for consideration and respect for their family moving forward,” The-Dream’s rep told E! News in a statement at the time. 

4. Kelly Rutherford and Daniel Giersch

Their story became a drama worthy of a Gossip Girls sub-plot as the actress filed for divorce from her husband of two years in 2012 while she was still pregnant with their second child. The reason for the sudden split was unclear at the time as she only cited “irreconcilable differences.”

In the years that followed, Rutherford and Giersch became embroiled in a fierce custody battle over the two children, though Daniel ultimately was granted full custody despite an appeal from Kelly. Their daughter and son, Helena and Hermés, currently live permanently in Monaco with their father. 

5. Mary-Louise Parker and Billy Crudup

The Golden Globe winner dated Crudup for six years before she got pregnant with their first child. However, while Parker was still seven months pregnant with their son, the Spotlight actor controversially broke up with her for Claire Danes. 

“That was a scary thing…That was really hard,” Danes said of the criticism she received during an SiriusXM interview with Howard Stern“But it’s okay, I went through it.”

“I was just in love with him and needed to explore that and I was 24…I didn’t quite know what those consequences would be,” she continued. However, Danes has been married to Hugh Dancy since 2009 while Crudup and Parker both are currently single. 

6. Denise Richards and Charlie Sheen

After a three year marriage, the Wild Things actress filed for divorce from the Two and a Half Men star in 2005 while pregnant with the couple’s second child, daughter Lola. Despite a brief try at marriage counseling, Richards pushed the divorce forward. 

7. Heidi Klum and Flavio Briatore

Before she was kissed by Seal, the supermodel briefly dated the Italian managing director of Formula One in 2003. By the end of that year, she had publicly revealed she was pregnant for the first time. While she gave birth to daughter Leni in May 2004, she and Flavio had already split. 

8. Kelis and Nas

After meeting at an after-party for the MTV Video Music Awards, the “Milkshake” singer and rapper dated for a year before getting engaged in 2004 and marrying by the following January. However, after four years of marriage—and while 7 months pregnant with their first baby—Kelis filed for divorce, citing the standard “irreconcilable differences.”