In 2005, in an interview while talking about his dressing styles, he quoted that his girlfriend does not like his style of dressing.He did not mention her name and he never quoted about her elsewhere till date.
He performed many theatre productions and won laurels for his performance.There are no details to whether he is still associated with her in a relationship. No woman has ever come up to the media with the news that she is Winsor’s girlfriend. He is not seen with any woman in a dating scenario.It is not known whether he is in any romantic relationships as of now. His romantic relationship is way off from the media. He is currently living in Cardiff with his working partner and co-star, George Rainsford.He is a secretive personality and has not revealed information about his dating life.He has had no girlfriends and has also never been married.When I go out I like to wear beaten-up jeans and a nice smart blazer jacket with a V-neck underneath - scruffy-smart, I suppose. In New York at the opening night gala of Play Without Words on Broadway.