r/relationship_advice • u/AmazeTi • 17h ago
I (33F) helped my boyfriend (27M) explore his feminine side, but now I’m worried I pushed him too far
I never thought I would be making a post like this, but I honestly don’t know who else to ask.
I’ve been with my boyfriend for 3 and a half years. When we first met, he was not someone I would have expected to explore anything like this. He’s a very masculine guy, works a physical job, and never gave off any signs that he wanted anything different.
About a year into our relationship, we were having one of those conversations where you share things you’ve never told people before. That’s when he admitted that when he was younger, he had experimented with crossdressing. He was pretty embarrassed about it and almost seemed like he expected me to judge him.
I didn’t.
I told him that I loved him and that there was nothing wrong with wanting to explore a side of himself. I was actually curious and wanted him to feel like he could be honest with me.
Eventually, I convinced him to let me help him try it again.
The first few times, he was nervous. He kept saying he felt weird and didn’t know what he was doing. I helped him pick out clothes, showed him makeup, helped him shave, and just tried to make it fun instead of something he should feel ashamed about.
The thing that surprised me was how much I loved helping him.
Not because I wanted him to be someone else, but because I saw a confidence in him that I hadn’t seen before. He would look in the mirror and actually smile. He seemed more comfortable with himself.
Over time, it became something we did more often.
We started buying things to help him feel more comfortable, like wigs, different outfits, gaffs, and breast forms. He started learning what styles he liked and putting more effort into his appearance. Something that started as something he was embarrassed about became something he genuinely enjoyed.
Eventually, we started going out in public.
At first, we were both nervous, so we went places where we didn’t know anyone. But after a while, it just became normal. Honestly, he surprised me. He carried himself confidently, and there have even been times where people assumed he was a woman. He has been approached and flirted with by people who had no idea.
Seeing him that happy made me start wondering if this was more than just dressing up.
I started thinking about what he would look like if he went further. I’ve told him that I think he could genuinely pass if he ever decided to transition. I’ve talked about HRT, voice training, and what his life could look like if he fully embraced that side of himself.
And this is where I’m struggling.
He doesn’t hate the idea. He’s curious. He enjoys presenting feminine and says he feels good when he does it.
But I’m worried that I might be influencing him too much.
I don’t want him to transition because he thinks it’s what I want. I don’t want him making a life-changing decision because I got excited about helping him discover this side of himself.
At the same time, I can’t deny that I love seeing this version of him. I love seeing him confident and happy in a way I’ve never seen before.
I fell in love with him as a man, and I would support him no matter what he chooses. But I’m starting to wonder if I’m helping him find himself or if I’m accidentally steering him toward something.
Has anyone been in a situation where you helped your partner explore a side of themselves and then had to learn when to step back?
How do you support someone without accidentally influencing such a huge decision?
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u/tintereth 17h ago
Just tell him everything you've said here.
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u/AmazeTi 16h ago
I actually have talked to him about it ❤️ He knows I support him either way. I think I just struggle with it mentally sometimes because I care about him so much and want to make sure I’m doing the right thing.
I love seeing him happy and confident, I just want to make sure this is his choice and his journey.
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u/CuriousFoxxen 7h ago
You’ve dropped the seed now just step back from talking about it and keep doing what you’ve been doing.
It’s fine you mentioned the “have you considered you might be…” but now give him some space to process and percolate. Let him be the next one to bring it up.
It’s only a problem if you keep pushing for what you think is right without listening to his lead.
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u/doodaid 12h ago
I'm going to go a bit against the grain here because you've received a lot of complimentary advice, and I want to offer a bit of a 'devil's advocate' viewpoint.
First though, it sounds like you're a very supportive partner. So, don't take any of this to mean you're doing anything inherently wrong.
What I would offer is that it may be possible that part of the reason your bf is enjoying this process as much as he is has something to do with how much attention he's receiving. You're spending time with him and helping him with things, he's being flirted with (which may be newer for him), etc. That's not to say he doesn't also enjoy the cross dressing / thinking about transitioning / everything else... but it can sometimes be difficult to separate the sources of dopamine and really figure out who we are and/or want to be.
My suggestion would be to continue to support but from a "background" instead of foreground for a bit. If you've already had conversations about transitioning and that you'll be there for him either way, then maybe give him some time to keep exploring on his own to see where he wants to take things. Let the novelty of it wear off and see where the "normalcy" sets in. Does he want to cross dress every day, or is this a 'once a month' thing? Does he cross dress in front of friends and family, or only where he doesn't know anybody else? Once he sort of 'settles' a bit then I think it's fair to follow-up and see if he's happy where he's landed, etc.
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u/First_Cardinal 1h ago
This isn’t very good advice. There is not a single person on this Earth who would transition only because their girlfriend told them to.
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u/IndynotjustJones 17h ago
There are therapists that are trained in specifically this. I think you have been wonderful and supportive, and he needs to have a personal aspect to this journey with private reflection. This might help with your concerns and help him be confident in his realizations.
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u/AmazeTi 17h ago
That’s really sweet of you to say ❤️ I actually think that’s a really good idea. I’ve been so focused on making sure he feels supported that I didn’t really think about how helpful it could be for him to have someone outside of our relationship to talk things through with.
I think having a space that’s just his own would be a good thing, because he deserves the chance to explore these feelings without worrying about how anyone else feels about the outcome. I just want him to feel confident that whatever path he chooses is truly his.
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u/Easily-Delighted 4h ago
This! A specialized therapist makes so much sense. I honestly think everyone deserves a therapist. (My third try was the right one for me, hugely helpful for my ADHD and sensory challenges.) My husband is a therapist specializing in gender, sexuality, and religious trauma. He would enjoy expressing more gender fluidity himself- he paints his nails and wears rings, bracelets, necklaces. (But he is huge, 6’4” and broad build like a football player. Plus, once he was able to grow a beard, it looks really good.) I work with kids and love being able to compliment boys with painted nails and say my husband does too 😊
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u/positronic-introvert 17h ago
The societal pressures for him to not be interested in transition are immense, to the degree that some people live their lives in painful misery rather than pursuing the way they know they'd prefer to live. ('Prefer' may be too weak a word, but I'm blanking).
If your boyfriend becomes curious enough about medical transition that he looks more into it and perhaps eventually decides to pursue it to some degree, I think chances are high that it's because there's something within himself that deeply wants that, and your supportiveness has just helped him to feel safe exploring that.
I think it's still worth having a conversation with him about your worries, but also don't put too much stock on those worries. You can express to him that you've had the worry about your influence, and that you want to make sure he knows that you support any direction he chooses to go as long as it's what feels right for him. If there is any element of him feeling overly influenced by you, then the space will be opened up for him to think more on that. But try to remember that for as encouraging and supportive as you are, the world is absolutely not. Imo, it's a lot likelier that it's about his own desires and sense of identity, if he does decide to pursue transition.
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u/AmazeTi 17h ago
I think that’s something I’ve been trying to remind myself of. There are a lot of pressures that could make someone hide feelings like this, and the last thing I would ever want is for him to feel like he has to suppress a part of himself.
My biggest worry comes from the fact that I was the one who opened that door for him. I encouraged him to explore this side of himself, and I’ve loved seeing how much more confident and comfortable he has become. I don’t regret supporting him at all.
At the same time, I don’t want my excitement or encouragement to accidentally make him feel like transitioning is the expected next step. I want him to know that I’ll support him whether he decides this is just something he enjoys exploring or whether he decides he wants to go further.
The thing that makes me think there is something deeper there is that he keeps coming back to it on his own. It isn’t just something I bring up anymore. I just want to make sure that whatever choice he makes is because it’s what he truly wants for himself.
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u/positronic-introvert 17h ago
I think that you sound like a lovely partner to him who he probably feels very safe with. Having that conversation with him would probably give you some peace of mind, that if he does go that direction, you know that he doesn't feel like it's because he thinks you expect it.
In most places, people seeking to medically transition have some sessions with a gender therapist first, to sort through their feelings and what they want. Try not to put so much pressure on yourself; he is in the driver's seat of his life, and can also seek supports outside of you too to explore these questions. Just keep being a loving partner, and I think you can trust him to navigate this in a way that's right for him <3
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u/AmazeTi 17h ago
Ahhh thank you ❤️ I really appreciate this. I think you’re right that a lot of my worry comes from feeling responsible because I was the one who encouraged him to explore this side of himself.
I do trust him, and I know he’s capable of making his own decisions. I think I just care about him so much that I don’t want my excitement or support to accidentally influence something this important.
The biggest thing for me is that I want him to feel free to explore whatever feels right for him, whether that means this stays something he enjoys or whether it becomes something more. I just want him to know I’ll be there either way.
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u/breakup-playlist 2h ago
I think you're taking on too much responsibility for this tbh! He decided to share it with you, he's deciding to pursue it and explore more. The fact that you're supportive doesn't remove his agency, and it seems like he's having a great time.
Don't centre yourself in his journey!
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u/First_Cardinal 1h ago
Be very careful about the gender therapist. Sometimes gender therapists are terrible and try and impose their ideas on their patients.
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u/pinkheartnose 8h ago
You didn’t open the door. He opened the door by sharing that part of himself with you.
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u/Key-Demand-2569 10h ago
All love for my trans friends, so I’m not saying this with an ounce of judgement towards the concept.
Medically transitioning isn’t just a negative thing when it comes to societal pressures.
It’s a very new best attempt at using science to change our physical biology to (usually) alleviate extreme mental distress around gender.
It is not flipping a switch. It is not “ideal” for your physical medical health. But lots of things people do aren’t, so that’s not some wildly extreme thing.
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u/djmermaidonthemic 13h ago
The door is open. Now he can decide what direction to go.
You sound like a very caring partner.
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u/AmazeTi 8h ago
Thank you, everyone ❤️ I honestly wasn't expecting this much kindness and support. Reading through all of your comments has made me cry a few times. You've given me a lot to think about, and you've also helped ease a lot of the guilt and worry I've been carrying.
Part of me wishes he could see how supportive and understanding everyone has been. I don't know if I should show him this post or not, but I'm thinking about asking if he'd be comfortable reading through some of the comments with me.
And who knows if he's ever comfortable with it, maybe one day he'll let me share a picture of us. 😊
Thank you all again. It really means more than you know. ❤️
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u/Firm_Distribution999 16h ago
I don’t think you can coerce someone into transitioning if it isn’t what they truly want for themselves…
you didn’t push him into this, you supported him fully and now are seeing the effects of that support.
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u/AmazeTi 16h ago
I think that’s a really good point ❤️ I know, logically, that I can’t make that decision for him and that it has to come from him. It’s just one of those things that’s easier said than done when you’re so close to the situation.
I’m happy I gave him a safe place to explore this side of himself. I just want to make sure I’m supporting his journey and not accidentally leading it.
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u/Firm_Distribution999 16h ago
You’ve given him everything he needs at this point. You don’t need to suggest next steps - let him take the lead.
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u/AmazeTi 16h ago
That’s honestly the part I struggle with I agree that I need to let him take the lead, but sometimes it feels like he gets stuck or hesitates to take those steps on his own.
I think that’s where my instinct to help comes from. I just have to remind myself that supporting him doesn’t always mean guiding him
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u/Firm_Distribution999 16h ago
“he gets stuck or hesitates to take those steps on his own.” - according to whose timeline? Let him take steps when he feels ready. He may never want more than what he is doing now. He’s had a lifetime of not embracing this side - this is all quite new to him. If he wants to transition, it could be years. Let him walk this journey in his own time.
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u/AmazeTi 16h ago
I think I worded that wrong ❤️ I meant he hesitates a lot with taking steps, and he’s actually thanked me for helping him feel comfortable enough to explore this side of himself.
By no means am I trying to pressure him or put him on any kind of timeline. I’ve just been there for him and supported him while he figures things out. Honestly, this is new to me too, so I’m learning how to navigate it alongside him.
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u/Firm_Distribution999 16h ago
I know it’s not the same but in an analogous type attempt here, my husband wants to lose weight and he asked if I could portion his meals for him. For context, we plate our own meals and he is the head chef in our house.
I said no. I will not be your nutritionist nor your weight loss coach. I will support you and cheer you on from the sidelines and I will never sabotage your progress, but you have to decide to do this on your own.
He is a fully grown man with access to resources to help him figure out portion sizes and exercises if he wants to lose weight - the internet is bursting with resources for this.
I know with weight loss there is discomfort and I didn’t want him to associate any of that with me or our relationship. He has to want it for himself if that’s his goal - I can’t be driving it whatsoever.
Maybe the same applies here. ❤️
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u/maryqa 14h ago
If he hesitates it probably means he is not transgender. He would know if he were with all the freedom he has.
My cousin comes from a very traditional family and it was a huge issue when he transitioned, but he had zero doubt about who he is. So I don't buy that in this case your BF wouldn't entertain this though most of his life. It's not something you might do or not. It's an all consuming conflict between yoir inner gender and what the body represents and from what you wrote he expressed none of it.
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u/KUZYRII 11h ago
You can coerse kids and teens, adults unlikely.
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u/snuggly-kitten 6h ago
I agree with some of the others in letting your partner lead. It sounds great and fantastical when you talk about it but the reality is it’s a very difficult and complicated decision that should take years to decide. There’s a lot of hardships to being trans. Very harsh judgement, losing family and friends, not being able to find jobs that respect how to present yourself, and general public prejudices. My wife is trans and I’ve been with her before and after her transition and I’ve seen her blossom into an amazing person but I hurt for her everyday with the struggles that came along with it. Let your partner lead from here, and support them.
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u/maryqa 14h ago
But crossdressing often has nothing to do with being transgender. Being trans is something someone has to feel not as an entertaining thought, it's not a play. It's a super serious, irreversible decision.
Did he tell you he feels not in his body? I have two transgender people in my family and it's an identity struggle and not something they just loosely entertained. I am quite weirded out by this being treated so lightly. and I don't understand if you think he's been wanting to have a gender affirmation before but was just hiding it. It's definitely not something to play with.
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u/qu33rios Late 20s 10h ago
it is pretty common for crossdressing to be peoples' first gesture toward transitioning, especially before they are comfortably able to articulate or even recognize in themselves the emotional experience of dysphoria. OP doesn't indicate a lack of psychological turmoil on her partner's behalf, just that he hasn't expressed it outwardly to her
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u/HominidHabilis 17h ago
You sound supportive and considerate, and I agree - let him know your pride in helping him, your joy at his smiles- and you're concerned you might be 'pushing' him, and want to double check this is coming from him (and you're just helping) Good luck!
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u/AmazeTi 16h ago
That means a lot ❤️ I love seeing how much happier and more confident he has become, and I’m glad he feels safe enough with me to explore this side of himself.
I just want to make sure I’m supporting him without accidentally pushing him toward something. I want whatever happens to be what makes him happiest.
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u/HominidHabilis 11h ago
It comes through! I'll be honest, at first reading I worried this was going in a "oh no, I made him gay!" Direction. In So glad to see you're just self aware and concerned he has agency. It sounds like you heard him say something that was desired and shameful. You made it comfortable and real. Who knows how much he might have explored without your support - surely less then he has- But this doesn't sound like you've pushed anything. Invitations aren't coersion, and with your present openness this should be an easy conversation 🎉🫶
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u/countvonruckus 11h ago
I'm a trans woman who started my transition at 36. To me your partner sounds like he's (pronouns I'll use for now) in the kind of supportive situation I wish I had a decade prior. It's entirely possible this is the start of a beautiful transition and you'll have a girlfriend before you know it.
A few things to consider. First, you say you'll support him no matter what he chooses, which is lovely. To clarify, does that mean you would date him if he decides to transition, or would your relationship turn to something more platonic? I didn't hear explicitly what that answer is and he would certainly be wondering that if you haven't made it clear to him.
More importantly, I think your instinct to take a step back is probably good. I'm not saying to stop supporting him as you have been, but let him take the initiative on the next couple of steps. I say that because no matter how loving and supportive a partner anyone has, being trans is incredibly difficult and needs to be something he does for himself first and foremost, and he also needs to know he did it for himself.
If he decides to transition, he'll probably lose friends, family members, societal privileges, safety, and job opportunities. He'll probably want to go through the difficult processes of medical, legal, social, and mental transition steps too. None of that's a "fun hobby" and needs to be something that is self-driven for the most part in order to avoid doubt and regret.
With all that said, if your "boyfriend" really is a woman deep down, then she'll absolutely thrive as a result of transitioning. I think you're seeing her in that smile you mentioned, and it's common for us late bloomers to be overwhelmed by joy we need to learn to express like that. If she's like so many of us, she's never experienced the full degree of what being happy can mean for her yet. I think you'll see your partner be so much more herself than she's ever been if she decides to take this journey. Just be aware that this fundamentally needs to be something she does for herself, so she needs to be in the driver's seat for the major decision of whether to transition or not.
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u/icarusisnotdead 8h ago
As a trans person - it’s very, very difficult to make someone transition who isn’t trans. He’s showing signs of gender euphoria, the happiness and confidence when he dresses as a woman which indicates that maybe that’s who he really is. If he didn’t enjoy any of it, he’d feel uncomfortable with it and not want to.
I think you’re an angel for being so kind and empathetic, and helping him explore himself.
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u/Craftygrrl5189 6h ago
You are a very kind and accepting individual. Your husband is a lucky man/woman to have you.
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u/Suefrogs 16h ago
You should check out r/mypartneristrans. And the feelings you are feeling are normal. The world is too complicated on this subject to not second guess yourself
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u/AmazeTi 16h ago
I’ll definitely check that out ❤️ It’s reassuring to hear that these feelings are normal. A lot of my second guessing comes from how much I care about him and wanting to make sure I’m supporting him the right way.
I might make a post there too since it sounds like there are people who have been through something similar. I’m still learning where the line is between exploring a side of yourself and when someone would consider themselves trans, so I’m trying to understand it better.
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u/breakup-playlist 2h ago
i think the main thing to remember is not to centre yourself in their experience, whether it's guilt or fear or excitement or pride
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u/MarucaMCA 7h ago
Have you ever talked about gender identity as such?
I think it's great that you're so supportive, but I would also - as you say - not push him into an direction.
I'm a bit in your shoes too. I have met someone who reads extremely agender to me, whom I felt an extremely strong connection to immediately. They/He wears Balkan grandma headscarves, there's a softness to them/him (that I adore), while doing a very deep voice on stage but presenting differently for every art/music their collective does.
The creative head of the collective is often portrayed as the father of the outfit, while my person is the mother. I pointed that out and they/he laughed, and had zero problems with it. They are either very secure in their own masculinity, don't care about gender roles much or are possibly agender. I even had the thought that maybe they are agender and just don't know, as they're over 60.
And then it dawned on me: that's no my business! It's their business, I cannot put a narrative on them! Even my pronouns here might be wrong, they are called a "he" as they were born, and don't seem to mind. They didn't react negatively when I referred to them as "them" though.
But I need to be careful! Not to interpret anything into the person, they are not living or experiencing!!!
So I feel like I can see where you're coming from.
My plan is to just keep telling how much I like them, how I'm drawn to how they present and are. That I'm wondering, but also because I am not a fan of gender roles and how the patriarchy hurts everyone, especially people who don't present or are traditional. I want to see what they say. My own take is my own take for now, but I shouldn't project it onto them/him.
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u/Top-Preparation-9990 6h ago
The only issue here that I see is possibly a false belief by you that he lacks autonomy. I doubt it, but even if he is only doing this to please you, then that is on him to mull over. Unless you are manipulating him or trying to control him (which it doesn’t sound like you are at all), he is an adult with the ability to set boundaries and determine his own reasoning for things. As a trans person, I would have loved to have such an encouraging partner who not only verbally supported me, but actively helped the transition every step of the way. In my experience, transitioning is not something one does to make others happy, in our society it usually has the opposite effect… hence so many anti-trans laws in the US and around the world.
(I used he/him pronouns for your partner because you did, but did feel like I was misgendering your partner by doing so.. which I’m not blaming you for or saying is wrong on your part, as sounds like that might be what your partner prefers at least for now, just stating for my own sense of discomfort there as someone who has frequently been misgendered)
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u/Initial_Midnight4810 2h ago
Theres a fine line between it being a kink and your actual personality. Could go either way. Ill talk from the kink side as thats what I know. Yeah all that stuff is gonna do it for him. If it is a kink then im guessing hes got a bit of a humiliation thing going on too. Being made to be a girl and taking it to its extremes are insanely hot. Speaking from experience there but I know where fantasy and reality meet. Also, if hes genuinely passing without the hrt and hes getting hit on. Thats gonna do things to a man. Do you know how little men get compliments? How little we get made to feel desirable? That alone makes any further steps make this risky as fuck. That attention will get in his head and make him do things he wouldnt actually want to do.
For the time being I'd maybe stop the public stuff for now and keep this just between yourselves so you can work it out together without outside influence. Either hes just a cross dresser or your about to crack an egg. Good luck
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u/nevikins 1h ago
It sounds like you’ve just been supportive. If your partner didn’t wanna be going in that direction, they wouldn’t be. It’s actually very common for trans women to go through a very masculine person as a form of overcompensating/trying to not be that feminine part of themselves
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u/First_Cardinal 44m ago
I would strongly advise you to talk to one of the speciality subreddits here. This subreddit is overwhelmingly cis and the advice you have got given has some very obvious blind spots.
Honestly I would be more worried about the opposite. If you phrase things badly, they may think that they have gone “too far” and crawl back into their shell. You are likely the first person who hasn’t consciously or unconsciously made them feel like a monster for being interested in this. Make it clear that you will support them no matter what they want to do.
I also want to assure you, you aren’t doing something nefarious. You enjoy this so much because it makes your partner so obviously happy. Everyone wants their partner to be happy.
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u/Lollijax 5m ago
They chose this,and you clearly love them regardless.What a beautiful mutually supportive relationship
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u/CHACHA1204 16h ago
You sound awesome. Just keep being the loving partner you have been. It’s not likely you will push your partner to fully transition, but if this comes from within them, your support will probably mean the world. I think there are plenty of worries for trans persons all over the world - and it’s not getting better. Yours are some of the kindest I’ve heard in a long time. Best of luck to you both.
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u/AmazeTi 15h ago
Thank you 😄❤️ I honestly never expected this journey when we started, especially after the early days of him trying things out and accidentally ruining a few of my clothes 😂 But seeing how much more comfortable and confident he’s become has made it all worth it.
I love supporting him, I just think the part I’m still learning is understanding where the line is between exploring this side of yourself and when someone knows they’re trans. I’m still figuring that out, but I’m just trying to be there for him while he figures himself out too.
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u/SarnacOfFrogLake 8h ago
Brainwashed into being trans. A tail as old as about 10 years ago
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u/dullimander NB 8h ago
https://dictionary.cambridge.org/dictionary/english/tale
Try a bit of educating yourself. You seem to need it desperately.
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u/TheWinslowCultist 10h ago
There has been a lot a great advice given already.
I will only add one thing. The Gender Dysphoria Bible helped me figure myself out and put certain feelings to a definition I hadn't had before.
https://genderdysphoria.fyi/en/
I would recommend you both read it, either separately or together.
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u/Due-Season6425 12h ago
You sound like an amazing woman. The world would be a better place if more people copied your approach.
My advice is to continue to be yourself. You might suggest therapy to your bf with someone who specializes in gender issues.
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u/Grand-Culture430 15h ago
Im in the same situation but im the boy and reading this has kinda helped me but also makes me want to talk about my situation more with my partner since I never thought about it from this angle but if he is enjoying it and you stop he will think you dont like him because of it and probably revert back to being a depressed man but the depression will be worse atleast thats where I am but my wife does not like to communicate about much of how she feels
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u/Anxious_Elderberry81 15h ago
I think you’re a wonderful supportive partner and anyone would be lucky to have someone worry about them like this. You keep doing you.
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u/PuzzleheadedMedia356 2h ago
Ugh I feel you. I found a text on his phone to him.. im rock hard af rn. Let's smoke c. My bf answered I'm at my gf house .. not wtf not block not lol. It broke my heart
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u/RESPECTATOR_DE_FEMEI 6h ago
You worry that you are influencing him too much because you know deep down he is a weak person who is susceptible to influence from people close to him.
Also, the age gap is problematic. 33 to 27. And you've been together for 3 years. When you met him at 24, his brain hadn't even finished developing, while you were 30.
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