Susan Boyle – 60, Singer

Susan Boyle charmed the world when she performed during the 2009 auditions for Britain’s Got Talent. She proved that we simply cannot judge people for their looks, for who would have thought that such a meek looking woman hid a powerful voice and stage presence? While fans from all over had fallen in love with the singer, it seems she’s not so lucky when it comes to the realm of romance. Nonetheless, Boyle thinks there’s no shame in living on her own terms. That said, she’s not entirely inexperienced when it comes to dating.

In 2014, she was reported to have been seeing an American doctor whom she met in Florida. However, their encounter didn’t progress any further from the one date they had. The singer admitted that while the guy was nice, he certainly was not for her. Given her busy lifestyle, Boyle simply could not afford the investments toward keeping up correspondence with him either.