We'll admit their relationship seemed weird at first -- Britney finding love with her agent? But the longer they were together, the more he grew on us. He was a guy who worked in the business and got what she did, but wasn't in the spotlight himself (at least not at first). And it really seemed like Britney was going to get her fairy-tale ending when Jason, 41, popped the question in late 2011. We were devastated when they split in early 2013. With a little time and distance, should these two find their way back to each other?