As a crossdressing man, you have a lot to offer in a relationship. Men who are wonderfully in touch with their feminine side tend to be sensitive and understanding about things that other men might not fully grasp. Whether you are straight or gay, you are likely to be open minded, and therefore a great partner for just about anyone.
Opening up about your crossdressing to someone you're dating might be easy, or it might be difficult. Often, people who are unfamiliar with the culture make assumptions that simply aren't true, such as thinking that all crossdressing men are gay, or that they are particularly feminine physically and emotionally. The reality is that most crossdressing men are attracted to women, and are typically masculine outside of their enjoyment of women's fashions.
The thing to keep in mind when opening up to a date is that, while everyone is different, most people like honesty. If crossdressing is an important part of your life, it's best to disclose early on. Depending on how the first date is going, you may want to say something then, or give it until the next meeting. Pushing it off until things get serious is not such a good idea, as your date might feel "led on" or that you're ashamed in some way.
When you do decide to tell your date, relate it with confidence, and show her (or him, as some crossdressers may be gay even though most are heterosexual) that you are comfortable with who you are. Healthy confidence is appealing to just about everyone, and may help to put an uncertain date more at ease. Be prepared for questions about crossdressing, as well as your sexuality and gender identity, and continue to give honest answers, even if there are things you're still figuring out yourself.
After you've made yourself clear, and your date has also been clear that she (or he) would like to continue the relationship, you can truly begin to get to know each other. While much of this will happen as it would in any relationship, the way you dress will certainly come into play. If you are someone who likes to crossdress in public, it may be wise to let your date know this beforehand. Although many people might be comfortable with it right away, others may need some time. Your level of interest in the other person can help determine how much you'll alter your own habits to accommodate her (or his) expressed level of comfort.
Be prepared to suggest dating environments where you know both of you will be at ease. Perhaps there is a certain restaurant or gallery that you frequent, or an especially welcoming group of friends who will support you by being patient with your new date. Whatever it is, you can both have a better time in such a positive atmosphere.
No matter whom you date, you must be true to yourself. Stay open to how the relationship might change you and the other person, and look forward to growing together in an honest and caring nature. And of course, have a good time!