Dear Wendy: “My Internet Boyfriend Is A Bisexual Cross-Dresser”

I’m dating a guy I met on the internet. We have never met but we text all day, and every night we talk on the phone and so far it’s been great. He’s really nice, very attentive and we have even said ‘I love you.’ But the problem is that he is bisexual and cross-dresses a few times a month. I’m kind of confused, but at least he is honest — we have talked about it and he has tried to calm me down and explain it to me. But I’m actually scared and I don’t know if I should run or accept him for who he is, have fun with the situation, and trust that he is going to be faithful and that he really loves me, because at the end of the day he is nicer than most guys I have dated. I really don’t know what to do, and I have to decide fast because he is coming to see me soon. Should I run? Do bi guys cross-dress or is that something only gay guys do? — Internet Girlfriend

I’ll answer your easiest question first: no, cross-dressing is not something that only gay men do. Bi guys do it. Even straight guys cross-dress and are able to maintain happy, healthy, monogamous marriages with women who are understanding and non-judgmental of their fetish. The harder question to answer is whether you should run, and my answer is: yes, but not for the reason you think.

The issue here isn’t that your internet boyfriend is a cross-dresser, something I think is ultimately pretty harmless if a couple is open and understanding about it. The issue isn’t even that your internet boyfriend is bisexual. Being bisexual, after all, doesn’t mean a person is any less capable of having a healthy, monogamous relationship than anyone else. The issue here is that you’ve never actually met this man in person and you’re already calling him your boyfriend and professing your love for each other. That’s scarier than anything else you reveal in your letter.

How much do you really know about this guy? And how do you know you can trust him? I mean, yeah, it’s commendable that he’s admitting to his cross-dressing ways and letting you know he’s bisexual, but how do you know he isn’t saying these things in an attempt to get you to trust him? You may think you’re in love with this guy because he’s nice to you and you text all day and talk on the phone each night, but that isn’t love. That’s filling a hole in your life with false companionship.

I’m not saying that there’s never potential for an internet relationship to develop into a real relationship offline; I actually know of several married couples who began as long-distance online paramours. But it’s a risky endeavor and there has to be something more pulling you together than “he’s nicer than most guys I have dated.” I don’t think I have to tell you that there are lots of sick people out there who prey on the loneliness of others. You’ve already said you’re “actually scared.” And you’re going to let this man into your home, why? Because he’s “nice”? This is a no-brainer: the risks simply outweigh the potential on this one.

My boyfriend is in the Army, and he’s to be deployed in a year. We love each other and have been contemplating moving in together. My mom and I are best friends, and one day she asked how I’m going to let my boyfriend deploy without marrying him first. I know he loves me as much as I love him, but it’s really starting to gnaw at me. I don’t know how I’m going to act or feel when he gets deployed and I’m starting to wonder if being married might be easier. What do you think? — Army Girlfriend

She may be your mom and your best friend, but this is definitely not a case of “mother knows best.” There are plenty of wonderful reasons to get married — being afraid of how you might act or feel when your boyfriend is deployed in a year is not one of them. Look, it’s going to suck when he gets deployed. You’re going to feel a host of difficult emotions, none of which will be any easier to deal with because you’re legally bound as husband and wife.

Being newly married is supposed to be a fun, exciting time in a couple’s life, but you’d have to put your celebration aside while you wait out his deployment. That’s no fun! Don’t start off a marriage missing your husband and worrying about his deployment. Move in together; go ahead and even get engaged if you want. But save married life for when he comes home. It will be worth the wait and make your time as a newlywed that much more special.

*Do you have a relationship/dating question I can help with? Send me your letters at [email protected]