Dating a Cross-dresser

Dating for a cross-dresser is complicated. There will be a point in a dating relationship where a cross-dresser will feel compelled to reveal their femme side to their new love interest before the relationship gets too serious. Many cross-dressers are divorced after many years of marriage. It may be their first or second marriage, most have kids and some even have grandchildren.

Because cross-dressing has been such a concealed way of life once the secret is told to their wives many are unable to save their marriage. The long-term secrecy and the fear of who her husband really is becomes a fast-track to divorce. Even with martial counseling, the prospect of having a husband who has a femme identity and a storage locker filled with woman's clothing is too much to handle for a wife who is not open minded. In many cases, revealing you are a cross-dresser is the final stance in a troubled marriage.

For these reasons, there is a growing population of divorced cross-dressers. Divorce is difficult for anyone who has gone through it. Even if the marriage is not perfect, none of them are, it still much easier to stay in a marginal relationship then to be single. Dating can be daunting. Dating for a cross-dresser can be darn right depressing!

My friend, who I will call Maggie AKA Paul, was married for 29 years and has two children in their twenties. Paul is a lawyer and hid his cross-dressing for the first twenty years of their marriage. Experiencing severe depression, Paul went to a specialist who suggested he go on female hormones to off-set abnormally high testosterone levels. Paul felt better, but started growing breasts.

Paul's wife barely tolerated his cross-dressing, yet could not deal with her husband taking hormones. Seeing his growing breasts was a turn-off for her and she demanded he quit taking hormones. Wanting to keep his family and marriage intact, he stopped the hormones. It still wasn't enough for her and they ended up getting divorced.

Paul entered the dating scene in his mid-60's. His femme side, Maggie, is a bigger part of his life now that he is free to be out, without repercussion from his wife. His children know about Maggie and have accepted their father, both as Maggie and Paul. According to Paul, he is one person looking for someone who embraces both his femme and male identities.

Yet, arguably Paul is more comfortable being Maggie. Paul is growing out his hair into a bob and proud of his breasts. He's back on hormones and electrolysis treatments. Paul has no desire to transition and is sexually attracted to women. He identifies with both genders as being who he is and continues to look for a woman who will love her/him for the total package.

Divorced for eighteen months, Paul has found dating to be challenging after having been in a relationship for almost thirty years. He has been seeing a woman and told her about Maggie after three dates, wanting her to learn more about his femme side. Paul wants to do it right this time, no longer keeping his femme side a secret and telling this potential love interest the truth from the beginning. Yet, he has found that this continues to be a challenge for him to find the right woman.

Dating is complicated for all of us. It seems like we can never find a mate. Yet, dating a cross-dresser is a new experience for most women and because cross-dressers have had this secret society, women don't understand them and think they are all transgender people wanting to transition into a woman, as if they are all Bruce Jenner's.

Here are some concerns women have when dating a cross-dresser and some tips for dealing with these issues:

  • Not knowing the difference between a transgender woman and a cross-dresser is an immediate problem for most women. Many women just assume that cross-dressers all want to be women and will transition at one time. The majority of men who are cross-dressers, have no interest in transitioning.  Get the data for her to help her better understand the community.
  • Does my cross-dressing boyfriend want to transition into transgender woman? This is a fear for women as they don't know how far their new boyfriend will go in the direction of his femme side and say to her one day, "I want to live as a woman full-time." The reality is some cross-dressers in their path to self-discovery, do. It is a valid concern and a new girlfriend needs to trust in the fact you won't.
  • Will I be sexually attracted to the femme part of my new boyfriend? This is another big issue for women who were initially attracted to the male side of their boyfriend. Seeing him in make-up, nail polish, heels and a skirt, smelling of Chanel perfume, is a very different visual for her that she has to explore. She wonders if she will have to make love with her boyfriend in his femme mode. She needs time to get to know your femme side.
  • How much of the time will my boyfriend be in his femme role? This is another important topic to cover with her as to what role your cross-dressing plays in your life and what she can expect from you.
  • Concern over what others will think about her dating a cross-dresser can be an issue. It complicates a dating situation. She may be concerned about introducing you to her friends, children and parents. You need to give her time to evaluate what she feels comfortable with. Be respectful of her life.

So, how does a cross-dresser find love? Like everyone else, through trial and error. Being upfront and honest, along with being comfortable with your own self-identity goes a long way in finding a mate. There's someone for everyone.