Dear Gabi, My Crossdressing Boyfriend Just Came Out but Now He’s Nervous and Depressed

Dear Gabi,

My name’s Angel and I have a crossdressing boyfriend, “Sullie”. We’re still in highschool, and have been dating for two years, but I’ve only just found out that he’s a crossdresser because he has been afraid to tell me because of how I may have reacted. I fully accept him, and try to encourage him to be himself no matter what. I am 1 of 5 people who know, but none of his friends or family know.

I’m almost sadden by the fact that he had took so long, after I’ve been very vocal on my opinions about Gay, Bi, Lesbian and etc decisions in life. I myself am Bisexual, but Sullie’s the only person for me.

He’s become a shell of himself and is still nervous when he dresses around me. He feels he is a freak, and “not normal.” This is what saddens me the most. His acceptance in society won’t be felt for a while. Like said, I fully, 100% support him in any way possible. He is himself, and that’s what I fell in love with, nothing less.

Our first year together, he wasn’t the most faithful, but something held me to him. Something told me to stay. After he came out, things have been so much better. We are stronger, and I can honestly say, I have never ever felt closer to him.

Sully has always had a quality about him, a shy nature. But as he has progressed in his nature and sexuality, he’s become ashamed of himself – not at all times, but it’s definitely a mental state of depression that I hate to see him go through. He’s never been sure of himself, inside and out. Now that I know, it’s boosted him slightly, but not enough for him to come out as Sullie to other people.

I sometimes get frustrated because some of the comments his friends make without knowing honestly offend him, but he can’t say anything. He’s 16. Do you have any advice for us? And advice for confidence for him?


Gabrielle HermosaDear Angel,

I can relate to Sully’s feelings of depression, nervousness, and feeling like a freak. Been there. Done that! It’s not easy growing up in a world that openly rejects and ridicules differences in people. Looking back at my own teen years, I’m amazed at how far I’ve come, in terms of conquering the feelings of shame and depression once tied to being transgender.

Your frustration is understandable. Watching the one you love experience these complex difficulties can truly be heart-breaking. The good news is that things do get better. Over time, being trans becomes less of a burden and more of a cherished personal trait. At least it has for myself and many other trans-folk.

A good first step on the road to feeling better about oneself is to reflect upon the reality of things and put them into proper perspective. There is nothing I can say that will magically fix anyone’s problems, but a little perspective goes a long way. Let’s shine a little light of reason into that murky fog of uncertainty that’s been causing so much trouble for you both.

Coming out is hard to do
Try not to feel like something is wrong because it took Sully so long to come out to you. Even if you may have welcomed the news from day one, it’s not as simple from a crossdresser’s point of view, especially at the age of 16. You seem like such an open-minded girl, and I’m sure Sully picked up on that early on. It’s a good bet that your being so open-minded and cool about differences in people plays a significant role in how he feels about you. Even so, the fear of rejection can be overwhelming.

Society is a little more comfortable, on the whole, with people being gay/lesbian. The haters are unfortunately still a plenty, but the majority of people will not have an issue in knowing that someone is gay. It is even reflected in entertainment very much today – gay characters are becoming more prevalent and are generally received positively. Crossing the gender line however, still has a long, long way to go. Crossdressing is still generally viewed as a mental illness, perversion, or many other negative things. Because it carries a significant level potential negative fallout in the eyes of many crossdressers, it makes it that much harder to come out.

If it helps any, I was 13 years into my marriage before having the confidence to come out to my wife. Needless to say, my own powerful insecurities about being transgender was a tremendous hurdle to overcome.

Feeling like a freak
I used to feel like a freak, too. So much so, that I really hated myself for being trans. I didn’t understand what it meant and was certain that if anyone ever found out, I’d be ridiculed right off the face of the planet. I would have rather died than have anyone find out. As I grew, evolved, and learned more, I felt less like a freak and became more comfortable with who I am. These days, several people know that I live part time in female form, and I’m not embarrassed about it in the slightest.

In high school, it’s pretty common for teenagers to feel like they’re a freak for one reason or another, at least at some point. I never shared my secret while I was still in school, but I remember several friends sharing things with me in confidence about why they felt like “freak”. The specifics are not important, but the reason was, and still is, always the same. The social structure in high school is all about conformity, being popular/well liked, and just plain fitting in. When something makes a teenager feel as if they don’t fit in, or wouldn’t fit in if others knew whatever (it need not be restricted to being trans), personal insecurities sprout up and wreak havoc on self-esteem. Once the nutty social structure of high school life has been left in the past, all those fears about being a freak, whatever the reason may be, fade away as little more than a bad memory about the strange beast known as teenage life.

It’s no news to you, Angel, but Sullie is most certainly NOT a freak – no more than I am, anyway. Crossdressing may not be very popular in mainstream society, and probably even less so in high school, but simply having unpopular personal traits does not mean anything is wrong or needs “fixing”.

The terrible things teenagers say
A sad reality among many teenagers is a frequent tendency to make fun of anything they feel they can chip away at. It may be just to get a laugh from friends, or intended to elevate one’s social standing by belittling others. The social structure in high school is so very different than the “real world”; life beyond high school. When you’re still in high school, it’s pretty hard to fathom any other way of life. Even if I or other survivors try to explain how different it is post-high school, it probably seems like so far away to anyone who still has a year or two or three left to go. Don’t get me wrong – people can still be plenty rude and barbaric, but it’s not as common, and the social structure is quite different.

Things are not always what they seem
There’s a good chance that Sully’s friends have no idea that what they’re saying is so terrible, or how it affects someone they call a friend. The mean-spirited remarks might be more of an attempt at “fitting in” or diverting attention away from themselves, than anything else. Perhaps certain comments are made primarily because “everyone else talks like that” and there is some “monkey see, monkey do” going on.

Unless you’re quite certain as to the underlying motivation for the mean comments, consider trying to find out. Passively studying the social behavior of people over time can reveal a lot about what is sincere opinion and what is automatic conformity-talk. I advise extreme caution should you choose to somehow confront said friends about it, though. By confronting them, potential to learn more, faster, is there, however it may also send out undesirable signals. I recommend the passive route here, unless your social prowess allows for a truly stealthy approach in your real objective when engaging in exploratory conversation with the offenders.

Some people are just shy
It sounds like Sully is somewhat shy and introverted by nature. There’s really nothing wrong with that. It’s a very common trait, and one that I share myself. Feeling ashamed of oneself when there is noting to be ashamed of however, is a different story.

Internalized transphobia
For many crossdressers, there is a strong sense of shame tied to the act of, and very real need to crossdress. Most of us, myself included, once viewed our need to crossdress as some kind of crazy compulsion that we couldn’t control, and it made no sense as to why. We’re taught (by society/peers) that we have to be “manly men” and anything not fully masculine is bad, wrong, undesirable, etc. Our need to feel and express femininity is in conflict with the social “norms” (note the quotes) of the masculine-only form and behavior that is expected of us as genetic males. That conflict, and feeling of being “all alone” in our differences, is part of what leads to the sense of shame. “We’re not like the others, therefore something must be wrong with us.”

Many crossdressers suffer from internalized transphobia. There is a fairly complex psychology behind it, but the short definition is the sense of shame that goes along with disliking (sometimes hating) oneself for being transgender. It is a learned behavior, typically caused by bearing witness to a lifetime of people expressing their dislike, hatred, detest, etc. for transgender people. That dislike and hatred can be expressed in a variety of ways, from mean-spirited jokes and disparaging remarks, to acts of violence.

Because internalized transphobia is learned behavior, it can also be unlearned. The realization that there is, in fact, nothing wrong with being trans and that it is a very normal (if not always popular) and common trait among countless men is a good start. Self-acceptance and embracing oneself as the person they are (as opposed as to what others may prefer them to be) is key to overcoming internalized transphobia and its devastating affects on one’s self-esteem. There’s nothing easy about stomping out this venomous demon, but if I can do it, anyone can, and that’s the truth. Anyone who truly wants to overcome the senseless shame can do just that.

Becoming more self-confident
I’m going to address you directly from this point forward, Sully. It’s easy to say, and hard to do, but it is absolutely true: if you believe, you can achieve. If you have a strong desire to be more self-confident; if you really want it, you will indeed achieve your goal. The key here is that you really have to want it, and not view it as a “nice to have, but…” kind of thing.

If your lack of self-confidence is, at least in part, tied to your being trans and a sense of shame over that aspect of your life, then I hope that you’ve been paying close attention to everything I’ve said so far. The feeling of being different, and the hurtful things others say about people who are different, may remain be a sore point for a while. If you choose to believe and embrace the truth over the bullsh*t lies and disparaging jokes, your insecurities about them will subside over time. It all depends on how you choose to look at things, and it is very much a choice.

You might consider writing down the things that bother and make you uncomfortable, either with who you are, or in how you feel others see you. After the list is complete, review and reflect. How many of the items are truly problem areas, as opposed to just feeling out of sync with your peers? I understand that just “feeling out of sync with peers” can carry significant emotional weight, regardless. If you keep the proper perspective about it, you may find that it’s better to be out of sync with certain people, than to be like them – especially if these people have a negative influence on how you feel about yourself.

Fake it ’till you make it
A helpful way to combat low self-esteem is to simply behave in a way that displays self-assurance and confidence to others. I’m not suggesting acting boastful or anything like that, but rather exhibiting a positive demeanor, carrying yourself with confidence, and putting out subtle signals that tell others you’re content and happy with your life, even if you don’t feel that way inside. It may not make sense to “pretend” feeling better, but this approach can be beneficial by creating a positive feedback loop. In other words, going through the motions (of feeling good/confident about yourself) can affect how well your day goes, which can in turn, have a positive affect on how you really feel, which will then create a more natural positive influence on how your day goes, etc. To be successful at it, you’ll need to be dedicated, practice, and work at it over a long period of time. You’ll also need to set some rules designed to keep yourself in check, such as: reflecting on how your day went, how your mood was, and what factors influenced them. Assess how you behaved and reacted to events that may have been stressful or upsetting, and what kind of signals you sent out to others in your reaction and subsequent behavior. Make a note of where you fall short of the kind of behavior you’d like to show the world, and think about what might have worked better if you had it to do all over again. Write them down as that can be helpful to strengthen your memory. Over time, you will be able to modify how you act in situations and even how you feel about them inside. This will only help if you work at it and stick with it long term. I hope you can put a little faith in the words of wisdom from someone who’s been there and truly understands what it’s like to experience the problems that have been troubling you.

It gets better
It gets better, Sully. That’s the truth. It may be hard to see when you’re 16 and stuck in “high school life” for a couple more years yet, but it will get better and you’ll soon be enjoying life as the beautiful person you are, rather than being ashamed of or embarrassed by it. There’s really nothing to be ashamed of… unless you intend to let others dictate the kind of person you’re allowed to be, and how you can and cannot live your life. Now that would be big a shame. I think you’re smarter than that, though.

Good luck
Many best wishes to both of you. There will be struggles and bumps along the way, but if you remain dedicated and patient, the rewards of your efforts will be well worth the investment.

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6 thoughts on “Dear Gabi, My Crossdressing Boyfriend Just Came Out but Now He’s Nervous and Depressed”

  1. “…some of the comments his friends make without knowing honestly offend him…”

    As Gabi has said, challenging those comments head on can be tricky, although in a non-confrontational situation, you might be able to pull it off. I think it’s a case of finding the right time and the right words to ask a person if they really meant it. By that, the old phrase of “if you had a friend like that, don’t you think you’d upset them?”

    Talking of old phrases, there’s an old English saying of “School days are the best days of your life.” That’s utter rubbish. :-) Life gets a lot better when you leave school behind!

    1. Thanks for chiming in, Lynn. :) And utter rubbish is absolutely right! Those “magical, memorable school years” were mighty rough for me. Life got so much better in so many ways after getting out of that harsh environment – a sentiment I’ve discussed with plenty of people, and I don’t think anyone has said the opposite.

  2. Hi! I can’t help but wonder if being an “outcast” during our school years is a universal problem for transgendered, etc? I had poor social skills when I entered the 1st grade & still had poor social skills when I graduated high school. Basically I didn’t know what to “do” so I kept mostly to myself — alternately shy & aloof. I think the worst thing for me was the fear. I knew I was different but had no idea why. I was always afraid that somebody would think I was gay & then everything would get worse. I did discover early on that I got along better when there were girls in the class. Anytime I was stuck in a situation of all guys someone would eventually decide that they wanted to fight me. Unfortunately I was not a fighter. Did get hit a few times, and that made me even more fearful. I thought at the time that they thought I thought I was better than them, but that was definitely not the case. Sometimes I wonder if they were picking up on my feminine side & really wanted to have sex with me but didn’t know what to do about it. I didn’t have a clue as to what was going on. I really preferred girl company, but never learned how to behave as a masculine date until I met my wife who was & is quite a tomboy. But let me pass on some advice — Don’t wait til 40 yrs of marriage have passed by tell your spouse. They can get really mad !!! *Note: I still have very poor social skills & it affects my life in many ways. I’ve never been able to attend a highschool reunion even as a guy. Gabe, I wish I had your moxie …

    1. I was pretty socially retarded in school too, Donald.  It made things that much more difficult.  I’m not sure that all trans folk experience related troubles in school, but rather those of us who struggled with it more.  Some people just deal with things better, even if they don’t understand what it means at the time.  I wish I could have been more like that in school, but I was one of the more insecure types, unfortunately.

      No matter.  The past can’t be changed, but I can take what I’ve learned in my own troubles and try to make a positive difference in the lives of others who struggle with the things that I once did.

      And yes, I did attend my high school reunion as Gabrielle.  The jerks that made fun of me back in school were there, and making fun of me again (laughing and calling out to me).  The difference this time was that I didn’t care.  They lost the ability to make me feel bad about myself a long time ago.  I enjoyed the company of a small groups of cool friends and paid no mind to the people staring and laughing.  I was nervous as hell at first, but had a great time and I’m glad I went.  Even though there was some laughing and mean spirited remarks being made about me (as I found out more detail later), no one gave me a hard time and everyone I engaged in prolonged conversation with was absolutely cool to me, including several people who I connected with via Facebook later on.  I’d say much of the class had indeed grown up and become a lot more open to accepting people for who they are. And just to be clear, the people I hung out with the most that night were just as cool when we were teenagers, too. I just could have never shared this aspect of my life with anyone back then.

  3. hey let him get dressed and sexy its fun and kind of cool.if everyone was same world would be doing video and im very happy about it,someday may be discovered but my panties not in a bunch yours shouldnt be either.if you accept his fem side you will grow super other doesntknow entirely but says things that make me suspect shes catching on.she caught me we cause i left pics on accident on her pc,lol awkward.don worry about him dressing he must like you trust you so return that girl! stay positive sexy ladies

  4. Of course he nervous and depressed . He would be judged.If not by you or your family or friends. By someone it could be bad or worse. Maybe not. I’m very good at studying people.I’m almostly right. Girls wear male clothes all the time. And don’t call it crossdressing. They call it fashion or style. And that’s normal girls. Right. Tell me why. I been trying to understand it. For a very time. And I thought did but I don’t. Not fully.

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