Trya Banks
Tyra Banks is one of the most famous supermodels in the world. After her modeling days were over, she chose to keep living in the spotlight with her own TV shows. At 46, she's never been married and has only been in a few "serious" relationships. She has a child with her ex-partner, Erik Asla, but now is rocking the single mom life.
Matthew Perry
Matthew Perry has been very forthcoming about his substance abuse and addiction issues, and still feels that he needs to work on himself. Despite being in serious relationships with the likes of Lauren Graham, Julia Roberts, and Yasmien Bleeth, he's never been married or even engaged. His last serious relationship was with Lizzy Caplan which ended in 2012.