14. Aly Raisman And Colton Underwood
Olympic gymnast Aly Raisman began dating Oakland Raiders tight end Colton Underwood after he asked her out via a video posted online. After seeing the video, Raisman described it as being “very cute.” She also opened up in the past about how the two managed to meet for a date as they happened to have a perfect lineup in their schedules. “We happened to both be in Denver at the same time. I was there for less than 12 hours, he was flying in for just a few days. It just ended up working perfectly.” The pair hit it off and went on a few more dates before making it official. Unfortunately, the pair split 5 months after Underwood’s video was posted online.