Coupled With D&S

Real, nonjudgmental advice about dating, sex, love, and life from a thirty-something couple that has seen it all over thirteen years.

Trust us. We live in Brooklyn. (Joking. Kind of.)

Cross-Dressing Conundrum

translegs translegsThe Question

A 42 year-old straight male who cross-dresses, is only interested in women, and only wants an LTR writes, “I’m stuck with a paradox: I have discovered that if I am not perceived as forthright from the start (I don’t always dress up, just like women don’t always dress up), the revelation of what makes me different can be off-putting. On the other hand, if I put who I am out there from the start, no one picks me. OKCupid has in the past provided women who pick me, and that has been extremely rewarding. How can I increase my ability to find women who would want, not merely accept, what makes me different?”

David Says

We’ve had the benefit of looking at this gentleman’s OKCupid profile. He’s a very good-looking, very masculine-looking man with facial hair. He appears to be in great shape, and he fits men’s and women’s clothing pretty well. We know that this guy will be in a very niche market because may women won’t think he fits the standard image of masculinity. He’ll have to take risks and face a lot of rejection.

  • Is it better to be up-front with your cross-dressing or hold back until you’ve made a connection first?  You’ve waited a month to tell a woman in the past, and that ended badly. I’m of two minds on this: Once you’ve made a connection with a woman, she might be more willing to accept your cross-dressing (think men who come out to their wives about this decades into a relationship). On the other hand, if you’re open, you might attract someone who’s really into your situation, which is the best place to be. Maybe have two different profiles and see what happens: one that is a celebration of your cross-dressing, and one that holds back a bit. People do it all the time with kinks.
  • You have to own yourself and be inviting. There are some women who will absolutely gush to find a hot, masculine, cross-dressing guy; there are some who will accept it; there are some who will always reject it. It’s important to tailor your profile to those gushers. You should treat your cross-dressing as a super power and a benefit as well as an invitation to excitement and adventure. It’s OK to think “and fuck you to all the haters out there,” but your profile should not focus on that. No one wants to meet someone who seems angry, defensive, or with a chip on his shoulder.
  • Your profile needs a tone shift. Building off my last point, your profile is pretty off-putting. It’s way too long, especially the first section, and you explicitly and implicitly bring up a lot of negative past experiences, hurt, frustration, and defensiveness at the beginning. Get rid of the negativity, focus on what you have to offer, and boil things down to the most essential.
  • Make sure you’re looking in the right place. I notice you list “bisexual” women only in your profile, which might make sense because they’re likely to be more open-minded, but is that the best place to look? You might want to be open to straight women too. Sally has more thoughts about location.

Sally Says

I agree with David about two things: branch out and stay positive. I did a little research, and here’s some suggestions.

  • Is OKCupid the right place to find a mate? OKC is best for garden variety straight, gay, and lesbian short-and long-term matches. Sites that are more specifically geared towards cross-dressing and less vanilla things might be a better fit. More likely, you will need to have a few different sites in your arsenal in addition. is one of the sites that I found in a few minutes of Googling. It’s geared towards men and women who are looking for someone just like you. It’s a niche site, however. If you’re looking for a larger site and willing to reach out to the trans community even if you don’t consider yourself transgender, you might try some of those sites. is a big one.
  • Use your personality in person. You seem like you have an exuberant personality and have a lot to say. Use it to your advantage by letting people meet you as a whole person, not just a few pictures on a dating website. I think there are probably plenty of women out there who are open-minded and maybe even a little turned on by men who break the rules, but there are just too many options on dating websites, and sometimes it’s hard to communicate the whole you. One of the best ways to use a dating site or a place like might be to find out about parties and meetups that you can attend in person so you can show people how cool it can be for a man to wear a skirt.
  • Tone and volume shift. From my perspective, it’s not just about tone, but about volume. The amount of information you give in your profile is overwhelming. Leave some mystery to be solved in person. We all like to see our potential partners have some filter.
  • Lose the beard. From a female perspective, you’re a cute guy and a cute “girl.”  If that’s what a real girl’s into though, I think she’d want a girlier looking girl when her guy’s going to be a girl.  Give it a try.  You can always grow it back.

The Consensus

To sum up, almost all of our advice to you involves branching out as much as possible and using what you offer to your advantage. Maybe it’s called better marketing, but the most important element of that will be community-building for yourself. We suggest:

  • Mutiple profiles on OKCupid as an experiment to see what happens.
  • Multiple dating sites, including more niche sites.
  • Focusing on in-person interaction.
  • Tone and volume shift.
  • Shave.

We both think that, if you moderate your tone and hold back on the info a bit, and if you branch out and make as many online and real-world connections as you can, your chances of meeting a great woman for an LTR will be greatly improved.