Britney Spears' Ex Charlie Ebersol Was Reportedly Ready To Propose When They Split

Britney Spears' dating history seems to be as long as her catalog of hits. While some of her relationships are well-known — such as her marriages to Jason A. Alexander, Kevin Federline, and Sam Asghari — the chart-topper almost got married one more time back in 2015 when her then-boyfriend Charlie Ebersol wanted to propose to her before they split. If Ebersol's name doesn't sound very familiar, however, it's because their relationship ended just as quickly as it began. 

The ex-couple began their relationship in 2014, and according to People, one source close to the situation at the time said they were "taking it slow." The "Toxic" singer met Ebersol through one of her assistants. "I thought he was really adorable and she said he was good to people, so I went for it. There was something about him that made me feel really peaceful and at ease," Spears told the publication at the time. 

Well, as with every relationship that happens in the spotlight, Spears and Ebersol went through some ups and downs during their short time together. But Ebersol was so sure that he wanted to be with Spears "Till The World Ends" (as the singer herself sang back in 2011) that he was prepared to do something headline-worthy at the time.

Britney Spears' romance with Charlie Ebersol wasn't as high-profiled as some of her other relationships with her exes like Justin Timberlake, Kevin Federline, or even her most recent husband Sam Asghari. The couple only lasted from October 2014 to June 2015. One source told People that year that the former American Alliance Football CEO took the breakup pretty hard. "Charlie has been pretty torn up about all of this," the insider said. "He really thought she could be the one. He is a very private, family guy and saw Britney fitting right in."

The news certainly came as a surprise for fans too, as back in March 2015 Spears told Extra that marriage was possibly on her mind when she was still with Ebersol. "You never know. Who knows? I'm very blessed to have him a part of my life," she said. 

Well, Spears probably said those exact same words soon after she met her future ex-husband Sam Asghari on the set of her music video "Slumber Party" in 2016. At least Ebersol didn't waste too much of his time crying himself a river over their breakup.

While Britney Spears' fans know that she certainly moved on with her life as she dated and married Sam Asghari following her split with Charlie Ebersol, the entrepreneur did the exact same thing. It didn't take long for him to fall in love and propose to his wife Melody McCloskey in Hawaii back in 2017. "SHE SAID YES!!! @melody thank you for making me feel loved, happy, and safe. I love you," he wrote on his Instagram page. The couple are now the happy parents to two adorable children, whom Ebersol often took on the field with him during his Alliance American Football games. 

Ebersol hasn't made any comments about his relationship with Spears since their breakup back in 2015, but it doesn't look like he needs to. However, he did seek comfort from both puppies and some prayers when his romance with Spears ended, according to his social media posts around that time. That's something Ebersol and Spears have in common, as the singer likes to surround herself with puppies whenever she's feeling the blues, too.