“My Best Friend Wants a Sex Change”

I’m a senior in high school, and so is a very close friend near and dear to my heart. He’s wonderful, kind, funny, and the sweetest soul I’ve ever encountered. Something I’ve always noticed about him is that he’s very feminine (be he says he isn’t gay). About a week ago he confided in me that he is most certainly a female — a lesbian — inside a male’s body. He told me he’s thought about it all his life, and he confided that he’s dressed up as a female a few times, just to see how it feels…and it’s very natural to him. He’s thought about it for a while now, and he’s made up his mind that he wants a sex change.

Immediately grateful that he shared such a personal thing with me, I hugged him and told him that I’d have his (her) back through the entire process. It seems to be a stressful thing to endure once the transition starts, and I’m very scared for him! He is deathly afraid to tell his family — something I’m a little worried about, too. They aren’t exactly the most accepting of people all the time, and I don’t want this to be more stressful for him than it already will be. But I don’t want to pressure him to tell them if he truly doesn’t want to.

Please help me. I just want to be a good friend and make sure he gets the body she deserves, so she can truly feel like herself. What should I do? — A Confused Friend

You already ARE being a good friend just by listening and accepting and loving. That your friend felt enough confidence in you and your relationship to share with you what she hasn’t felt safe enough to share with anyone else speaks volumes about your character and the bond you have together. Just keep being there for her and accepting her for who she is. She has a long journey ahead to match her outside with who she is on the inside, and she will likely be faced with plenty of opposition and judgment along the way — sometimes from people who are supposed to love her unconditionally.

You can’t help how anyone else reacts to her or even how she handles the challenges she’ll be faced with. But you are in full control with your own behavior, and that’s what you should focus on. Let your friend know how much you care about her and how you’ve got her back and that, no matter what happens, she has your support. That will mean more to her than you probably realize.

As far as your friend telling her family, you need to let her decide when and how to do that. This is, above all, her journey. She may invite you along for some of it, but you have to respect that she is in the driver’s seat just as you are the driver on the path you’re traveling. Let your friend decide whom to tell and when and how, and just be there for her to support her however you can.

Your friend WILL get through this. Thousands and thousands of people undergo sex changes in various forms all the time and go on to have wonderful, fulfilling lives with partners and families and careers and everything anyone else may have or want. Whether your friend has her family’s support or not, she’s going to get through this. Obviously, it’s much easier and less lonely to have the support of loved ones, but, if your friend isn’t lucky enough to get that, at least she has you. And she will find other support too. On the TransEquality website, I found a list of support groups for transgendered people, as well as healthcare links and resources for legal support.

Your friend does not have to be alone through this process and you do not have to be her sole support system (nor should you take on that responsibility). There are people who have the wisdom and experience to help guide your friend through the various choices she’ll need to make. And on your end, it’s important to remember that your friend is, indeed, going through a process and she’s only at the very beginning of it. She may make some decisions now that she’ll change her mind about later on. And that’s OK. As teenagers, you BOTH will be growing and changing in different ways, and you BOTH are figuring out who you are, what your identity is. Be gentle and compassionate with each other, and understand that there will be times when it’s YOU who needs support. Don’t be afraid to ask for it from your friend. Over the course of a long journey, friendship is a two-way street… even if one side of the road has more obstacles at various times than the other.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. Wendy has some great advice here. One thing that she hints at but doesn’t state outright is using the right pronouns to refer to your friend. Ask your friend what pronouns they’d like you to use. Does she think that female pronouns are right for her? Does he still want to stick with the more-familiar male pronouns? Do they think deciding pronoun usage is too much to think about and want you to use the singular they/them? I mention this because it can be a very simple way to affirm your friend’s identity.

    I wouldn’t recommend pressuring your friend to do anything, though. Coming out is a hard personal decision – watch this TEDx talk about how everyone has a closet to come out of: http://www.upworthy.com/a-4-year-old-girl-asked-a-lesbian-if-shes-a-boy-she-responded-the-awesomest-way-possible (Note, I usually hate upworthy but this is a great video.)

    Maybe your friend thinks that her family would kick her out of the house if she came out as a woman. Maybe your friend wants to get through college as a guy before telling her family, so she doesn’t have to pay for it all herself (if she’s that lucky to have help paying for college, even with strings attached.) Maybe her family will be super-supportive immediately, and her worries will be unfounded. Who knows? But it’s a tricky thing to consider. I would simply support your friend’s decision, not try to persuade her of the right course of action.

    Good luck to your friend in realizing and appreciating her gender identity! And congratulations to you for being such a good friend that she trusted you with this information – it means that your friend thinks very highly of you.

  2. I just love this letter— LW, you’re a great friend, as well as a sweet & understanding person. You are already being very supportive, so just listen to Wendy on the details & continue doing what you’re doing. Good luck to you—& of course, your friend—on the journey.

  3. I think it’s great that you’re concerned about your friend, but really, other than being supportive (which you’ve already done), you can’t really do anything. Getting a sex change is a long and drawn out process, so it’s not like your friend is going to physically become a girl in the next few months. There are hormones to take, counselors to see, surgeons to meet with. Also, it all takes money. Probably lots of money. So anyway, just be a friend through this process. Show love and support, and don’t treat your friend any differently than you have been.
    Also, do what Christy said and ask if your friend would like to be called by a feminine name or by his male name.

  4. WWS. Like everyone said, you’re already being a good friend. One thing that Wendy mentioned and that I believe is extremely important to keep in mind is to let your friend have control over who should come to know she’s trans and that she wants to transition. This is sensitive information because unfortunately trans women are still often the victims of bullying and even violence. I don’t mean to scare you, and I hope your friend will be safe. But don’t tell anyone about this unless your friend has given you permission to do so.

  5. I think Wendy and everyone else here has given some excellent advice. One thing I wanted to add about the parents is that there’s a lot of gray area between the worst case scenario (they totally freak out and disown her) and best case scenario (they are 100% supportive and non-judgmental). If they’re just curious, doubtful, shocked, or reluctant, the LW’s friend should be prepared to work with them to help them understand what she’s going through. I learned this when my brother came out to my parents — they were kind and accepting, but they revealed to me privately that it was a big adjustment for them and it would take a while to get used to that new reality. That doesn’t mean they hate gays or that they were anywhere near disowning my brother — quite the opposite — but I guess what I’m saying is that if the parents aren’t immediately 100% accepting, there’s still hope. Don’t despair if they need some time to wrap their heads around things. The LW’s friend will find herself in the unique position of learning that when a kid comes out to her parents, compassion has to go both ways — that the parents should try to be compassionate and understanding of the child, but that the child also might find herself being called on to be compassionate toward her parents while they struggle to understand what the child is going through. Give that process as much time as it needs. These things aren’t always black and white.

    1. YES- About the parents! Even if they’re the most accepting, loving parents ever, it’s going to take them a while to wrap their heads around this MASSIVE change. They’ve spend 18 years having a son, and it’ll surely take them a while to adjust to the idea of having a daughter. That’s totally normal, and it’s ok.

    2. You’re totally right about the adjustment thing, but if the friend’s parents do indeed react badly to her coming out at first, I feel that LW’s main role is to support her friend. LW can point out that the parents may come around over time, but s/he shouldn’t defend the parents if they are hurting her friend with their reaction.

      1. I agree the LW’s main role is to support her friend. But she might be able to give her friend comfort and hope by telling her that an initial bad/startled reaction by her parents isn’t unconquerable. There is hope. I know that when many people come out to their parents, they fear the worst possible reaction. Because they’re keyed up, they can be sensitive to anything seemingly negative, and interpret it to mean the worst is happening (I’m mostly basing this on my brother’s coming out, but also many other people I know). As a support person, it can help to comfort them and talk to them about how a parent’s initial reaction might not be as bad as they felt it to be. Even though my parents reacted well to my brother (and mostly shared their limited qualms with me, not him) I still spent a lot of time reassuring him afterward that everything was okay. The LW should be on her friend’s side, but that doesn’t mean she can’t also help her see where the parents are coming from. That is actually helping the friend, too, if it makes the friend less afraid of potential disaster.

    3. Avatar photo shanshantastic says:

      Totally agree with this. When my brother-in-law came out to my in-laws it took them a bit of time to adjust. They love him and have accepted the new normal with open arms, but they had a lot of confusion and preconceived notions that they had to deal with, and I really give them a lot of credit for seeking counseling to help them process everything. I also credit my brother-in-law with being SUPER compassionate and understanding toward his parents – it really helped that they worked together and today their relationship is better than ever.

  6. As a teacher I can’t tell you how many times I’ve confronted teenagers in both middle and high school about treating students who identify as LGBT with respect. “That’s so gay” is unfortunately still a common phrase, not to mention the much much worse things that I’ve confronted. It’s sad to see how many students still have a lot of hate for others just because they are different.

    But you, LW, are so supportive of your friend and that is AWESOME. I’m so happy there are people out there like you who aren’t judgmental and who offer a safe space for people such as your friend. The biggest way you can support her/him is to be there when they need you. Be a safe space for them and let them know that you’re there. It’s going to be a tough road, and any support they can get is going to help.

  7. Bittergaymark says:

    If your friend is deeply concerned about how his parents will react — then he absolutely should NOT come out to them until he is out of the house amd living on his own… Coming out when you aren’t in a safe situation is often the path to homelessness and prostitution.

    1. I have to agree here, and was about to post the same thing until I read BGM’s post.

      You are doing all that you can at your age/station in life by being accepting of the change(s) (to come) and being an ear/shoulder for your friend. Right now, that’s all you can do, other than give that link provided.

    2. I definitely agree. One of my best friends is a lesbian and she came out in high school when she was 16 and her (very conservative) parents definitely didn’t take it very well. She said she had a bag packed for years, just in case she needed to run away at a moment’s notice.

    3. Yep. There’s a significant number of teenagers who are living in poverty or homeless because they get thrown out by their families. I don’t like to suggest that someone hide who they are, but this is something to consider. Getting kicked out can change the entire trajectory of someone’s life.

      1. Super true. Some estimates have it at 40% of homeless youth being LGBT. Definitely worth considering the monetary and just generic “roof over one’s head” ramifications of a big decision like that. citing sources:

  8. Married by Elvis says:

    This letter is such a refreshing change of pace from the headache-inducing letters from grown-a$$ people who act like they’re in high school and wonder why maybe it’s a bad idea to move your new boyfriend of 3 months in with your children. This is a high school student who’s acting like a kind and compassionate adult.

  9. I agree with BGM. I don’t want to be all doom and gloom, but especially if your friend is already very afraid of coming out to her parents, she should be careful. I live in the south and while many people are very tolerant, I know a lot of gay/lesbian/queer people who were kicked out of their house, completely shunned, physically beaten, or told that they deserved to die by their own parents. And that doesn’t even cover trans people and the unique difficulties they face.

    I know in my city they have a support group for trans youths in helping them come out to their families with a safe place/a mediator to do that. I’m sure a lot of those types of groups exist, if your friend is interested. But, of course it’s her choice to make that and you can support whatever she chooses to do or not do. You sound like a wonderful friend for what it’s worth.

  10. I agree with everyone here; I would also add that, if you feel it’s appropriate, you can encourage your friend to consider starting therapy. A qualified therapist can help your friend with gender identity, family, and social issues that are connected to this. This is a huge burden for a young person–not necessarily being transgender, but being transgender in a scary and intolerant world. Furthermore, I once read (not sure if it’s true) that getting the green light for sexual reassignment surgery (if your friend chooses to go that route now or in the future) in most states requires at least two years of counseling/therapy. It wouldn’t hurt to have this under your belt if you’re planning on having an operation or considering heading in that direction one day. But above all, remember that your friend is young and needs love and support more than anything.

  11. I’m going to talk about my experience, when your friend told u that, she has so much confidence in u because that’s not a easy thing to say to someone, even your bestfriend, so, I think u must support her in the process and don’t tell everybody cause that will only make her feel worst, be kind and compressive and give her all the love u can. When she finish the process, u must congatulate her.

  12. Hey,
    Where should I start? I definitely think that your friend will appreciate the effort you are taking to be the right friend for them.
    I would suggest asking for their pronouns. Maybe they want you to keep using he/him until they transition or maybe that could cause them dysphoria and they want you to use she/her. Either way, that it’s valid and you should let them know that.
    As for the coming out, if I was in their place, I would make sure that I had a safe place in case my parents decided to kick me out. Maybe you could offer them that place? What do you think?
    I hope everything turns out great for both you two.

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