When to tell my eHarmony matches about my cross-dressing?

As to some of your friends telling you that you should hide until she is hooked - that's the worst advice on the face of this planet. You already tried and where did that get you? You are alone - that's where. Why would you want to waste your time and hers when something like this stands to be a major deal breaker. There is something else to consider too - she may be fine with it, but may dump you because you were manipulating and deceiving her - an even more bitter pill to swallow.

Also, I'd suggest looking at joining dating sites that cater more to alternative lifestyles rather than mainstream. You are much more likely to find someone who would be into the idea there.

First.....you are not really being up front and honest when you say something along the lines of "I'm a little kinky" in your profile. That could mean a million different things. So the matches give you the benefit of the doubt and proceed, but really they are just waiting for an opportunity to ask you about it. Once the real truth is on the table, of course they'll be making the decision whether to continue or not. Why are you upset by that? You should be expecting it and you do seem to realize that this is not appealing to most women.

As to some of your friends telling you that you should hide until she is hooked - that's the worst advice on the face of this planet. You already tried and where did that get you? You are alone - that's where. Why would you want to waste your time and hers when something like this stands to be a major deal breaker. There is something else to consider too - she may be fine with it, but may dump you because you were manipulating and deceiving her - an even more bitter pill to swallow.

You have to be realistic with yourself. Your interest certainly limits your dating pool. Disclosure will cause many women to run away - totally to be expected. However, remember something important - you are trying to find a woman who would not be put off by that. They are out there, but it will take patience to find them.

Also, I'd suggest looking at joining dating sites that cater more to alternative lifestyles rather than mainstream. You are much more likely to find someone who would be into the idea there.

How frequently do you dress?

cross-dressing tends to say to many that you are still in the closet....

I absolutely agree with the statement in red. I don't think it is a first date disclosure, as so many first dates do not lead to a second. However, ANY piece of information - health, sexuality, work or family issues - anything that could have a significant impact on a potential partner's decision to preceed, should be disclosed ASAP.
Don't risk letting someone develop affection or attachment and then make an announcement that you know could have negative impact. This is when hurt and resentment set in. Do it early, before there is any entanglement.

I disagree. There are many things you don't disclose on a first date or in OC that could cause your date to run for the hills. And it's good advice to tell people to not "let it all hang out" on the first few dates. The point of a date isn't full disclosure; the point of a date is to make enough of a good impression that you can get a second date.

I think cross-dressing is something that women will put up with if they know a guy and like him a lot, and want to stay together, but will not put up with if it's mentioned on a profile. It's true that this was not the case for his ex. That doesn't mean it's not the case for other women.



I suggested this to him already, too. If he insists on telling people upfront, alternative sites are the best option.