No Masks Allowed: Dating When Your Teen Is Transgender

Should I wait until I am in a serious relationship and absolutely sure the guy is right for me and will be supportive of my son? If I do wait and find that I have developed feelings for this man only to discover that he won't be supportive of my son, then I must end the relationship. So since I won't know how supportive he'll be until I take off my mask and test the waters, that's what I do.
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My first date, at age 16, told me he had a record. It was not an old vinyl record like our parents played on record players; it was a criminal record. He was 17 and Puerto Rican. His name was Milton, and he was sweet, but he had a secret he couldn't keep in. He'd been with his friends in New York City when an older man had yelled at them and called them "spics," which is a derogatory term for someone who is of Latin decent. It had infuriated them, so they'd beaten up this old man and his adult son, who'd been with him. But they hadn't just beaten him up; they'd beaten him to death. Milton said the old man's son had identified Milton, who was only 14 at the time. Milton had gone to juvenile detention for three years for manslaughter and had just gotten out. I must admit I thought about dating him still, because he had been honest with me, and he seemed so sweet, but I don't believe in violence of any kind for any reason, so I just couldn't get past it. This first date would foreshadow my dismal dating future.

We all wear masks every day. We smile at the boss we would prefer to frown at. We embellish our experience in job interviews. We say we are doing great to passersby who ask how we are even though we may be feeling very sad. We take on that one favor for a friend and act as if it's no bother even though we are bogged down at work. But we never wear masks more than we do in dating.

Bars are not my scene, so, for dating, I have resorted to the mask to match all masks: online dating. It is a strange experience. You will find a large dating pool, but what is real and what is fake? Everyone on an online dating site boasts about how ambitious they are and how accomplished they are. They claim to work out regularly. They claim have "little baggage" and to be carefree. They all enjoy long walks on the beach and traveling. They all post glamorous photos and seem to be perfect until you meet them. The thing is that no one is perfect, and we all have some baggage. I have a whole truckload myself, and I refuse to wear a mask in that regard.

My first dilemma in dating is when to tell someone online that I am physically disabled. My disability isn't something I am ashamed of or something I could hide even if I wanted to. I am proud of all the obstacles I have faced and conquered, but potential dating partners don't always see it that way. When first mentioning my disability in an email to a dating partner, I try to make a joke of it. I say something like, "I am physically disabled, and my disability is noticeable. I am proud of my disability and wouldn't change it, but I am afraid running marathons is out of the question." Some guys laugh at this and have no issue with it. Other guys take the marathon metaphor seriously and run far away in the opposite direction. One time I met up with a guy I hadn't told ahead of time, and I quickly regretted it. We met at a restaurant, and when he saw how noticeable my disability is, he actually yelled, "Well, this isn't going to work! I love physical activity like skiing!" Instead of crawling under my table and pretending not to know him (who am I kidding? I couldn't physically get under the table if I wanted to!), I sat with him and ate dinner. I did make the best of it by slipping the hot waiter a note after dinner saying, "You were the best part of my date," and leaving my phone number. I never heard from the hottie or the rude date, but I got a chuckle out of it nonetheless.

Now that I've somewhat conquered my disability when dating, how do I introduce the fact that my 16-year-old son is transgender? I don't yet know a funny way to bring that up in conversation. When asked about my son, I can't exactly say, "Well, I thought my child was a girl, but it turns out I was wrong and he's a boy. Please pass the bread." Then again, maybe I could. But the question is when. I mean, talk about removing all masks, right? I also have to consider my son's privacy. What if this date goes no further? Should I wait until I am in a serious relationship and absolutely sure the guy is right for me and will be supportive of my son? If I do wait and find that I have developed feelings for this man only to discover that he won't be supportive of my son, then I must end the relationship. So since I won't know how supportive he'll be and how open he is until I take off my mask and test the waters, that's what I do. Everyone who is close to me and my son is aware that my son is trans. The fact that my son is trans is not my whole life or his, but it is a part of our lives, so there is no reason to hide it. I am an open-book type of person, and I believe keeping secrets makes you sick. So typically, when there's a guy I wish to date, I tell him within a few emails that I am disabled and that my son is transgender. I then wait for his reply. If he is negative or ignorant, then I know he isn't the guy for me. If he is supportive and open, then I'll continue on to the first date and see where it goes.

Dating with no masks on doesn't just apply to me; it applies to my son as well. I worried when he came out to me as trans at age 12: Would he be able to find someone to love him? Would girls want to date him? Would he be accepted? Would he be hurt? For transgender teens, dating is a whole different ball game; in fact, in can be downright scary. The statistics on violence against transgender people are startling. One study found that more than 50 percent of trans individuals have experienced sexual violence at some point in their lives. So with my 16-year-old son, my rule is that he must tell a potential date that he is transgender before they go on that first date. As you know, teens are not always great at following rules, but my son and I agree on this one. He is forced to remove his mask early on, and it's served him well. As it turns out, dating is much less of an issue for my son than it's ever been for me! He gets girlfriends left and right and sees me as an old spinster! It doesn't matter, though; seeing him happy makes up for the wise-cracking teenage remarks. My son is upfront about the fact that he's transgender with every girl he dates. Some girls won't date him because he is trans, but many are supportive and open. It helps that he's darn cute and a great young man, but what really helps is his increased confidence. I truly think he's been able to have so many girlfriends because, unlike the rest of us, his mask is off completely. He is able to be his true self 100-percent, and how many of us can truly say that? I've learned so much from my son, and to truly remove my mask is just one of the important lessons he's taught me.

The Trisha TV show did a brilliant special on transgender teens that highlights a teen couple dating that I've included below (and I'm proud to say that Hannah, the lovely 12-year-old girl at the end, is a friend of my son's and mine):

Even with my series of horrific dates, I still truly believe in great love. Lately, one couple in particular has renewed my faith in the existence of true love with no masks allowed. Every morning, when I enter my office building, I see a cute elderly couple saying goodbye. One morning I noticed that the man was giving his wife a little bag of Bruegger's bagels for breakfast. I asked her if he was bringing her breakfast. She told me that every morning her husband drops her off at work and comes back and brings her a bagel and her favorite French vanilla coffee. He then comes back later and takes her to lunch. She described to me how they met and fell in love 47 years ago on a blind date and how they are still in love. I asked her to tell me her secret, and she said, "I got lucky." I said, "I think he's pretty lucky too." That, my friends, is real, movie-like true love.

I believe that whatever our differences may be, we all want the same thing: to love and be loved in return. I suggest that we all begin by taking off our mask; after all, as H. Jackson Brown Jr. says, "Sometimes the heart sees what is invisible to the eye." So the only mask I'll be wearing from now on is on Halloween.


I'll be myself, baggage and all, because I still believe and hope that I'll be lucky enough to meet the man with my French vanilla coffee.

Mary J. Moss is a feisty single mom to a terrific, almost-16-year-old boy who just happens to be transgender. You can reach her by email at

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