Cross Dressing Confession: How Should You Tell Her?

Ask Dan & Jennifer Sex, Love and Dating Advice From the Most Popular Couple Online Jennifer: I think it’s on. Okay, yes it’s going. Dan: It is going. Okay. Jennifer: You guys are going to be shocked, okay. We don’t agree on this one. Dan: No, we disagree and you know that’s okay. Sometimes it happens even with us. So okay, check this out. This guy wants to know, “How do I tell my girlfriend that I cross dress?” And it’s an important thing to him. So okay, he says, “Hi guys, I need some advice. I’m 19 and I have a small fetish, a little bitty of cross-dressing. I know I’m straight and I’ve had 3 good relationships with women. I only cross-dress in total privacy and I do it about once a week. The girl I'm dating at the moment is great and I really feel we could go all the way. But to do this, I need to be totally open and honest”. Yes. “Would you tell her? If so, how? Any advice will be much appreciated. Will she accept my Cross Dressing? Jennifer: Okay, we both agreed that you should definitely tell her, it’s the how that we may differ on. Do you want to go first or me? Dan: No you first there. Ladies, beautiful, hot ladies always first. Jennifer: Okay, well first of all one of the guys in the forums has recommended a great website called CrossDressers.com, it’s got a lot of information but if you go to the forums and search for “How to tell your partner?” I posted a great link in there that actually has some more details on that. Dan: How do they get to the forums Jennifer? Jennifer: Just go to our website AskDanandJennifer.com and click on the forums or if you’re already watching this on YouTube, we’ve got a link in our profile. Yes? Okay, and I’ve had a very informative article that I happen to agree with and Dan was like, “No, that’s not the right answer. So we’re going to talk about it and then you guys can chime it at the end and tell us which approach you think this guy should take? Okay, I think this is a very serious thing. It’s a part of your life. It’s not the same as being gay but it’s kind of a big deal and I don’t think you should surprise her. I think that’s a really bad idea, I don’t think you should leave subtle hints laying around. You know, I think you got us a, “Hey look, I need to talk to you about something, I really like you and I think I can see our relationship going somewhere but there’s something I need to talk to you about”. And I guess, you can get to sit down and have a heart to heart talk with her and make sure that you’ve done all your research ahead of time and find out because she’s going to have a ton of questions, you know. About well, does this mean you're gay? You know, does this mean— Dan: Are you going to be spontaneously turn gay? Jennifer: Yes. She’s going to have all kinds of questions and she’s going to be like, “How much of a cross-dresser are you?” Or you know, “Do you just like to put on lingerie? Do you like to do the whole full drag, make-up and everything?” But the important thing, you got to have a heart to heart talk with her. And also, be able to answer her questions. That was kind of my thing, but Dan thought that was a little too much. Dan: Look, I think your approach is going. We both agree, open and honest. You can’t have secret fantasies behind your partner’s back, otherwise, because that keeps an artificial distance between you two. Jennifer: Yes. Dan: I’m just not a big fan of the sit down, heart to heart on things like that. Jennifer: Most guys aren’t which is kind of interesting but this is a girl. I think she’ll be open for it. But most guys are like, “Oh god, we need to talk? I’ll see you next week.” Girls are all about the heart to heart talk though. Dan: Look, I just think that this is a perfect opportunity to slowly ease into it. That’s just my approach, I’m sorry. Jennifer: How do you slowly ease in into telling your girl friend that you need to cross-dress? I’m going to put you on the spot. Dan: Fine. Look, I think this is great thing to sneak into a fantasy box when you’re both anticipating what are we going to do tonight and you know you certainly— Jennifer: I’m going to dress up like a woman? Dan: Yes. You know, if you’re going to—I’m sorry. You just don’t setup a lunch meeting and you know, “Okay, we got to sit down and have a heart to heart—because she’s thinking, “Are we going to break up or what?” Jennifer: Well, then she may be relieved, that he’s going to be—that he’s cross dressing? Dan: I just think that fantasy time may be a better time to really, time of fun, of strong sexuality of fantasy time. I think it’s a perfect time to drop a subtle hint and see how that might go. What’s the subtle hint? How? I don’t know. You might accidentally drop a pair of—get a pair of new things or whatever. You know get her a new bra or whatever then you try it on, “Oh, let me, oh, that’s so soft. Let me try it on.” I don’t know, this is not my thing. My point is, with anything, you can typically drop a hint and see how the hint is received and then go further. You can typically warm your audience with more few hints at a time. Jennifer: Okay, so guys, what do you think, okay? Drop hints or have a heart to heart talk? What do you think is the best approach? Leave a comment and let us know what you think. Dan: I'm sorry, dropping hints is not really right. I think the slow and steady backward around the bend sort of approach. I don’t know. Jennifer: Okay, so, what do you think guys, heart to heart talk or slow backward around the bend approach? Dan: Backwards? What’s the right way Joe, we want to know. Leave a comment. Don’t forget subscribe to our Channel. And rate our show, give us 5 stars!