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Feminism: Sex and gender discussions

How do you support other siblings when a teen decides they are trans

663 replies

Autumnleavesareslippery · 07/10/2024 09:13

I've name changed for this, have been a member for 19 years since pregnant with DS. I'm going to try and be factual as I'm in shock and dealing with a whole host of mine and my children's emotions. Yes I'm using 'he' here as none of us have got our heads around this. I'm trying to be very honest in how I feel and really need some support from people who have more of an idea about how to handle this than me.

DS (19) came home from uni on Friday. On Friday night at about 11 pm in the family chat he declared he was transgender. He informed us what he was called. It was an unusual name choice for a 19 year old - that of someone perhaps born 150 years ago. Think Enid. He told us he'd known for years.

All of us were in shock. I have DD (17) and DD and DS (both 14). I sent a message privately to him thanking for letting us know as I wasn't quite sure what else to say. He didn't read it and remained in his room. Didn't even bother with the usual teen response of a thumbs up.

Saturday and Sunday he acted completely normally, like nothing major had happened and he had told us he was vegetarian now or something. He seemed calm and relaxed. He looked exactly the same - a 6ft 2 broad shouldered man.

He then came downstairs to get a lift to the train station dressed as what I can only describe as a stereotype of what someone might think a woman looked like. Badly done make up. An odd dress that didn't fit. And started talking in a completely different soft 'feminine' voice and doing strange things with his hands that he must have deemed 'female'. He had lace like gloves on. It looked so outdated and strange.

The best way to describe it was he looked like Dame Edna or the character out of little Britain from 20 years ago in that the clothing was odd and it seemed almost designed to get a reaction. But he appeared to be deadly serious and nonchalant about it. A woman would have been clearly mocked if she dressed like it. It just leaves me wondering whether this is what he views women as?! Not that he knows any women who would act like this - he's surrounded by many women who express themselves in multiple ways but not in an Edwardian lady about to collapse way.

I drove him to the station trying to make small talk about the weather and his course and came back to everyone sat staring in disbelief. He's never said anything, acted in any way 'feminine' (whatever that means). He's at a RG uni, studying a science subject with 3 As at A level, and has organised himself a part time job. I only say this because life seems to be going well for him, rather than a potential response to something.

He is however autistic.

DD 17 is furious and says he's making a mockery of women and that woman is not a costume. She says he better not be going in female only spaces.

DD 15 looks stunned and keeps asking why he thinks he can just become a woman and what he thinks that means. She can't identify out of periods etc etc. DS 15 is laughing in disbelief. DH just looks completely confused and keeps muttering about getting loads of tattoos when he wanted to shock his parents thirty five years ago.

I genuinely don't know what to do next. Please bear in mind I'm in shock, had only just 'got over' my first born leaving for uni and all the emotions that brings.

I want to support DS19 with whatever gender expression he wants. When he still looked like him (and didn't appear to be 'dressed as' a mockery of women) I was shocked but we just thought ok, this is him experimenting with finding himself or whatever. But now I'm really worried about him and his future and whether others will look at him and think wtf. I'm also angry at the very (sorry to stereotype) 'teen boy' way he told us - late at night, no response, informing us what he was called rather than perhaps asking 'could you call me'. No consideration of the impact but I guess that might just be being 19.

I agree with what both of my daughters are saying. How do I say this because it then directly criticises DS? Do I accept he is an adult, has made his choices and my care and focus should be on them? I can't gaslight them and tell them they're wrong.

I'm now worried he's going to go into female spaces, as a clearly visible six foot plus male. This would make me angry.

He is at a university where I know lots of his lecturers (I am an academic in the same field). I know many are gender critical. Do I mention it to them first or let it be the elephant in the room?

I don't know what to say to my 85 year old mother. I think she will be very shocked and worried. I'm trying to work out if we have to tell her (she doesn't live nearby).

I don't know how much to talk to him or challenge this. I feel a kind of grief. I'm worried he's going to take hormones or do something irreversible.

We all dislike the name / think it's a very odd choice - which makes me feel very alienated from him.

And at the end of the day he's my 'baby' - I want him to be happy. I don't want people to criticise him. I want to support him but how do you do that when you question so much what he is doing? It wasn't the fact he declared himself to have a different gender but rather what followed - the declaration of name, strange clothing and fear of him going in women's spaces.

I also do absolutely realise he is an adult and can make his own choices and face the consequences. He has his own life (albeit he's being financially supported by us).

I guess it was just so sudden.

Any advice on what to do next would be gladly received.

OP posts:
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colourfulchinadolls · 07/10/2024 13:13

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Lovemusic82 · 07/10/2024 13:19

As soon as I started reading I was thinking “is he diagnosed autistic” and then read that he is.

My DD is 20, in her 3rd year at uni and came out as trans during first year. She’s not masculine in the slightest but also never been into make up or clothes. She pretty much just wears what a 50 year old would wear, comfy clothing, slightly gender neutral. I have just been going along with it now for over 2 years in hope she will grow out of it, I’m not sure what else I can do? Dd is very immature (socially) and since being at uni has been in her first friendship group which happens to be mainly autistic trans and gay students.

I totally get how your DS’s sibling is feeling, she knows how ridiculous he looks and probably doesn’t want to be seen out with someone who is trying to imitate a female really badly 😬. Let her say how she feels to his face, she’s allowed to air her views and she’s allowed to refuse to be seen out with him.

Demonhunter · 07/10/2024 13:19

Autumnleavesareslippery · 07/10/2024 09:13

I've name changed for this, have been a member for 19 years since pregnant with DS. I'm going to try and be factual as I'm in shock and dealing with a whole host of mine and my children's emotions. Yes I'm using 'he' here as none of us have got our heads around this. I'm trying to be very honest in how I feel and really need some support from people who have more of an idea about how to handle this than me.

DS (19) came home from uni on Friday. On Friday night at about 11 pm in the family chat he declared he was transgender. He informed us what he was called. It was an unusual name choice for a 19 year old - that of someone perhaps born 150 years ago. Think Enid. He told us he'd known for years.

All of us were in shock. I have DD (17) and DD and DS (both 14). I sent a message privately to him thanking for letting us know as I wasn't quite sure what else to say. He didn't read it and remained in his room. Didn't even bother with the usual teen response of a thumbs up.

Saturday and Sunday he acted completely normally, like nothing major had happened and he had told us he was vegetarian now or something. He seemed calm and relaxed. He looked exactly the same - a 6ft 2 broad shouldered man.

He then came downstairs to get a lift to the train station dressed as what I can only describe as a stereotype of what someone might think a woman looked like. Badly done make up. An odd dress that didn't fit. And started talking in a completely different soft 'feminine' voice and doing strange things with his hands that he must have deemed 'female'. He had lace like gloves on. It looked so outdated and strange.

The best way to describe it was he looked like Dame Edna or the character out of little Britain from 20 years ago in that the clothing was odd and it seemed almost designed to get a reaction. But he appeared to be deadly serious and nonchalant about it. A woman would have been clearly mocked if she dressed like it. It just leaves me wondering whether this is what he views women as?! Not that he knows any women who would act like this - he's surrounded by many women who express themselves in multiple ways but not in an Edwardian lady about to collapse way.

I drove him to the station trying to make small talk about the weather and his course and came back to everyone sat staring in disbelief. He's never said anything, acted in any way 'feminine' (whatever that means). He's at a RG uni, studying a science subject with 3 As at A level, and has organised himself a part time job. I only say this because life seems to be going well for him, rather than a potential response to something.

He is however autistic.

DD 17 is furious and says he's making a mockery of women and that woman is not a costume. She says he better not be going in female only spaces.

DD 15 looks stunned and keeps asking why he thinks he can just become a woman and what he thinks that means. She can't identify out of periods etc etc. DS 15 is laughing in disbelief. DH just looks completely confused and keeps muttering about getting loads of tattoos when he wanted to shock his parents thirty five years ago.

I genuinely don't know what to do next. Please bear in mind I'm in shock, had only just 'got over' my first born leaving for uni and all the emotions that brings.

I want to support DS19 with whatever gender expression he wants. When he still looked like him (and didn't appear to be 'dressed as' a mockery of women) I was shocked but we just thought ok, this is him experimenting with finding himself or whatever. But now I'm really worried about him and his future and whether others will look at him and think wtf. I'm also angry at the very (sorry to stereotype) 'teen boy' way he told us - late at night, no response, informing us what he was called rather than perhaps asking 'could you call me'. No consideration of the impact but I guess that might just be being 19.

I agree with what both of my daughters are saying. How do I say this because it then directly criticises DS? Do I accept he is an adult, has made his choices and my care and focus should be on them? I can't gaslight them and tell them they're wrong.

I'm now worried he's going to go into female spaces, as a clearly visible six foot plus male. This would make me angry.

He is at a university where I know lots of his lecturers (I am an academic in the same field). I know many are gender critical. Do I mention it to them first or let it be the elephant in the room?

I don't know what to say to my 85 year old mother. I think she will be very shocked and worried. I'm trying to work out if we have to tell her (she doesn't live nearby).

I don't know how much to talk to him or challenge this. I feel a kind of grief. I'm worried he's going to take hormones or do something irreversible.

We all dislike the name / think it's a very odd choice - which makes me feel very alienated from him.

And at the end of the day he's my 'baby' - I want him to be happy. I don't want people to criticise him. I want to support him but how do you do that when you question so much what he is doing? It wasn't the fact he declared himself to have a different gender but rather what followed - the declaration of name, strange clothing and fear of him going in women's spaces.

I also do absolutely realise he is an adult and can make his own choices and face the consequences. He has his own life (albeit he's being financially supported by us).

I guess it was just so sudden.

Any advice on what to do next would be gladly received.

I'm with you DD 17, it was my first thought too before I even got to that part.

Have you asked him why he thinks he is and what he thinks a woman is?

Silvers11 · 07/10/2024 13:20

Do you think he is confused between being trans and simply wanting to cross dress @Autumnleavesareslippery ? His choice of clothing sounds more like he thinks it's the same thing as being a drag artist? Hope you can chat to him and see where he is coming from without putting any pressure on him?

Brefugee · 07/10/2024 13:22

Newterm · 07/10/2024 12:07

I think it’s a shame there isn’t a New Romantics or Goth revival. Young people would be able to find their tribe and dress up like Steve Strange without having to declare themselves trans.

gosh i miss those days. All those beautiful young men like David Sylvian in perfect eyeliner...

Back to OP. Hugs. This must be incredibly difficult. But since your OP relates to the siblings rather than your 19 year old, i think you need to let them know that they have your ear, and your shoulder. and that they must feel free to let you know about their feelings, worries and fears. Your DDs sound as they have a fairly good grasp on what is at stake for them, and how womanhood isn't a costume, just be open with them all.

I also agree with PP - if your 19 year old is going to be going places with you, then they need to be dressed occasion and weather appropriate. That was the rule for me (new romantic then full on goth) growing up, and was for my DCs growing up. Not dressed appropriately? then you're not coming with us.

Time will tell, i suppose.

ElleWoods15 · 07/10/2024 13:23

MrsSkylerWhite · 07/10/2024 13:05

BinkyBeaufort · Today 13:02

I'd assume he was taking the piss, and do the same back. A few episodes of Little Britain's laydees, leaving a packet of tampons on his bed, stuff like that.
Or I'd dress up in his clothes and make him call me Uncle Ned”

Would you? Would you really?

Sadly @MrsSkylerWhite I fear she probably would, as would some other posters. I hope neither @BinkyBeaufort nor @nosmartphone have children in their care.

Demonhunter · 07/10/2024 13:26

If he thinks to dress feminine he needs to say he's a woman there's men like Jeffree Star and the fabulous John McLean that shatter that stereotype.

MounjaroUser · 07/10/2024 13:37

Does he commonly have intense passions that peter out after a while? Have there been people at school when he was younger that he's tried to emulate?

I wonder whether he was attracted towards the trans community at university because he was familiar with them at school (not personally) and knew they would be welcoming, where he found other groups harder to break into, and whether there's someone there who dresses in an outlandish way who he's trying to copy now.

Itisjustmyopinion · 07/10/2024 13:39

If he is trans then he requires support and so does the wider family. But to me this all seems as if it’s a bit odd, maybe even a dare. Is there a chance he has been put up to confuse his family as a piss take by friends (or people pretending to be his friends?)

The random late night announcement via text when you are in the same house
The old fashioned name
The odd clothes - he has teenage sisters, surely he knows what their style is
The voice and mannerisms

I don’t know maybe he is starting to transition but there is something that doesn’t quite add up in this situation

Autumnleavesareslippery · 07/10/2024 13:39

OrlandointheWilderness · 07/10/2024 11:42

Your family sound lovely OP. I suspect that no matter how things end up in a few years you will still have a lovely family. I don't envy you this challenge- I actually am not sure how I would address it.

Why is it transwomen never dress like me!?! Jeans and a hoody, no make up and nails. No fancy hair etc. I would have far, far less of a hard time getting my head around it if a true reflection of womanhood was represented, but no. It's always a stereotype. A bit of a strange one in this case too I'm afraid.

This. No female in his life dresses like this. Nothing else has changed. He has always had ‘gentler’ for want of a better word characteristics of being kind and open and supportive of others. That certainly doesn’t make him female. It’s all surreal.

And thank you.

OP posts:
Autumnleavesareslippery · 07/10/2024 13:41

MounjaroUser · 07/10/2024 13:37

Does he commonly have intense passions that peter out after a while? Have there been people at school when he was younger that he's tried to emulate?

I wonder whether he was attracted towards the trans community at university because he was familiar with them at school (not personally) and knew they would be welcoming, where he found other groups harder to break into, and whether there's someone there who dresses in an outlandish way who he's trying to copy now.

This I think. He’s always struggled socially particularly with fitting in with male friends as didn’t like some stereotypically male stuff (like many many men!). I fear it’s about acceptance and can only hope right now this is fluid and if he finds his feet he might realise you can have any characteristics and hobbies you want without being a woman

OP posts:
MounjaroUser · 07/10/2024 13:44

What's he usually like when choosing clothing? Does he copy what his friends wear? Is he happiest when his clothes conform with others?

I would be paying him a visit at university to see how he is there. Actually I'd be worried in case he was having a breakdown.

GatherlyGal · 07/10/2024 13:45

Autumnleavesareslippery · 07/10/2024 13:41

This I think. He’s always struggled socially particularly with fitting in with male friends as didn’t like some stereotypically male stuff (like many many men!). I fear it’s about acceptance and can only hope right now this is fluid and if he finds his feet he might realise you can have any characteristics and hobbies you want without being a woman

My daughter is like this OP. She is autistic and has always liked having short hair and wearing androgynous clothes. That used to be fine but now not being a "girly" girl or a "manly" man seems to mean you need to transition.

People actually told her she was a boy and needed to transition. That along with the desperate desire for friends and connection and being gay have all lead her to believe she's a man.

Autumnleavesareslippery · 07/10/2024 13:47

Thank you everyone. I feel somewhat better.

I really wish I could challenge him like I would other behaviours but it’s a mix of fear of pushing him away, him sharing it with activists that his mum challenged him (I have a somewhat public profile) and worrying about his mental health. Or encouraging him further if it’s rebellion of some kind.

I think I will be open with the other DC and say I don’t understand either. I just feel a real sense of loss and anger at the woman parody appearance.

OP posts:
SophiaCohle · 07/10/2024 13:47

There have been some great posts on this thread, including some very brave ones from parents I assume are to some degree traumatised by their own child's transition. Plus the usual rubbish from Dadjoke et al. I sometimes think this is a topic people shouldn't post on unless they have personal experience of it. God knows, there are enough of us now who do.

I'm not going to go into great detail about my son's mtf transition but I will just say that in my experience your son will most likely have been groomed online some time ago @Autumnleavesareslippery. As an autistic teenage boy, possibly also questioning his sexuality and struggling with the 'category error' being autistic and gay represents, I imagine he will have spent a lot of time online and will undoubtedly have stumbled across people who make it their mission to suck vulnerable people into their ideology. It's like a cult. He will have been told that only they understand him and his feelings, that only transitioning will make him feel better about himself, and that his family need to be told how it will be and if they don't understand/have any doubts/try and talk him out of it, they (you) should be cut off without hesitation. He will then likely have sought out the trans community at uni, who will have emboldened him to put into practice the nonsense his head was filled with online. I don't want to alarm you with "go along with it or you'll lose him" messages, because personally I don't think colluding with delusion can ever be helpful, but I can say with some certainty that there will be people around him whose mission it is to provoke estrangement, just as any cult's first task is to isolate targets. Unless he desists voluntarily, my feeling is that you may already have lost him anyway, as he's likely been targeted for a lot longer than you realise.

My belief is that trans ideology is an insidious offshoot of the toxic masculinity/MRA movement, and that its main goal is to reinforce gender stereotypes and erode sex-based women's rights. It's interesting to me that TRAs seem to hate and mock middle-aged women in the same way that incels hate and target young women. I think that a well-funded men's rights movement is simply using young, autistic, often gay, people and pretending to champion their rights while actually hating them and encouraging them to pursue a course of action that effectively removes themselves from the gene pool via the effects of cross-sex hormones - erasing them, in fact. I am sorry, OP, that your son - and mine - have been victims of this hateful movement. I wish I knew how to counter it. All I can recommend is to stay true to your own beliefs as a means to avoid falling through the looking glass yourself, and to support the brave women who publicly stand up for fact-based discourse.

LBFseBrom · 07/10/2024 13:48

AnnaMagnani · 07/10/2024 09:19

Given the reaction of his siblings, I'd let them argue it out with him. And tell him he looks ridiculous and what does he actually think women dress and sound like.

I agree. Leave it to your d

It seems that he is more likely to want to try out being a transvestite than a transsexual with all that entails.

It may not last.

Just carry on as normal. Or 'as usual'. See how it goes.

FrostFlowers2025 · 07/10/2024 13:59

Autumnleavesareslippery · 07/10/2024 13:47

Thank you everyone. I feel somewhat better.

I really wish I could challenge him like I would other behaviours but it’s a mix of fear of pushing him away, him sharing it with activists that his mum challenged him (I have a somewhat public profile) and worrying about his mental health. Or encouraging him further if it’s rebellion of some kind.

I think I will be open with the other DC and say I don’t understand either. I just feel a real sense of loss and anger at the woman parody appearance.

Nah, he's doing it for attention. He probably gets a lot of it an uni and it's flattering his ego.

Ignore, ignore, ignore. Just call him whatever he wants (name, pronoun). Have a frank discussion with your other kids and explain to them to that he probably does it for attention and his ego. He is only 19 after all. Don't tell them they are wrong, but try to make them understand not tot get baited into any stupid discussions.

I think the best standard response from now on will be "That's nice, dear." He'll get sick of it at some point if he doesn't get rewarded with the attention he wants.

Autumnleavesareslippery · 07/10/2024 14:04

SophiaCohle · 07/10/2024 13:47

There have been some great posts on this thread, including some very brave ones from parents I assume are to some degree traumatised by their own child's transition. Plus the usual rubbish from Dadjoke et al. I sometimes think this is a topic people shouldn't post on unless they have personal experience of it. God knows, there are enough of us now who do.

I'm not going to go into great detail about my son's mtf transition but I will just say that in my experience your son will most likely have been groomed online some time ago @Autumnleavesareslippery. As an autistic teenage boy, possibly also questioning his sexuality and struggling with the 'category error' being autistic and gay represents, I imagine he will have spent a lot of time online and will undoubtedly have stumbled across people who make it their mission to suck vulnerable people into their ideology. It's like a cult. He will have been told that only they understand him and his feelings, that only transitioning will make him feel better about himself, and that his family need to be told how it will be and if they don't understand/have any doubts/try and talk him out of it, they (you) should be cut off without hesitation. He will then likely have sought out the trans community at uni, who will have emboldened him to put into practice the nonsense his head was filled with online. I don't want to alarm you with "go along with it or you'll lose him" messages, because personally I don't think colluding with delusion can ever be helpful, but I can say with some certainty that there will be people around him whose mission it is to provoke estrangement, just as any cult's first task is to isolate targets. Unless he desists voluntarily, my feeling is that you may already have lost him anyway, as he's likely been targeted for a lot longer than you realise.

My belief is that trans ideology is an insidious offshoot of the toxic masculinity/MRA movement, and that its main goal is to reinforce gender stereotypes and erode sex-based women's rights. It's interesting to me that TRAs seem to hate and mock middle-aged women in the same way that incels hate and target young women. I think that a well-funded men's rights movement is simply using young, autistic, often gay, people and pretending to champion their rights while actually hating them and encouraging them to pursue a course of action that effectively removes themselves from the gene pool via the effects of cross-sex hormones - erasing them, in fact. I am sorry, OP, that your son - and mine - have been victims of this hateful movement. I wish I knew how to counter it. All I can recommend is to stay true to your own beliefs as a means to avoid falling through the looking glass yourself, and to support the brave women who publicly stand up for fact-based discourse.

You’re spot on. A lot of people I know are very ‘be kind’ / fully accepting of this in children who are hypothetical and not their own. Having it explode in your own life also leaves the anxiety that maybe you’re not accepting about everyone leading their own lives as you thought you were. But it’s not a case of acceptance it’s anxiety for them, hurt from the parody of womanhood and grief.

OP posts:
Dandelionsarefree · 07/10/2024 14:05

Autumnleavesareslippery · 07/10/2024 13:41

This I think. He’s always struggled socially particularly with fitting in with male friends as didn’t like some stereotypically male stuff (like many many men!). I fear it’s about acceptance and can only hope right now this is fluid and if he finds his feet he might realise you can have any characteristics and hobbies you want without being a woman

I agree with this.
I read a while ago in a newspaper article in my own country that there are groups on the internet targeting teens who don't feel they fit in, and the mentioned teens with autism or social anxiety. These groups seem to be very welcoming in those forums and that brings young people to feel that they can fit in somewhere for the first time.

I am sorry you are going through this OP, my own country became very "progressive" allowing teens to start using hormones from early age, and even go though surgery to change their gender, many of them regretting such a huge/ irreversible change in their body's years afterwards. It's a total disgrace if that's the right word.

You sound really lovely and reasonable. I hope this will pass sooner rather than later x

Autumnleavesareslippery · 07/10/2024 14:07

FrostFlowers2025 · 07/10/2024 13:59

Nah, he's doing it for attention. He probably gets a lot of it an uni and it's flattering his ego.

Ignore, ignore, ignore. Just call him whatever he wants (name, pronoun). Have a frank discussion with your other kids and explain to them to that he probably does it for attention and his ego. He is only 19 after all. Don't tell them they are wrong, but try to make them understand not tot get baited into any stupid discussions.

I think the best standard response from now on will be "That's nice, dear." He'll get sick of it at some point if he doesn't get rewarded with the attention he wants.

Oh this is what I am hoping and you’re right I need to be honest for my other children. ‘That’s nice dear’ was the response in my head initially which I changed to ‘thanks for letting us know’ because it felt so casual and unreal. When he dressed like he did he looked like a lost little boy playing dress up.

OP posts:
CowboyJoanna · 07/10/2024 14:12

OP, I normally don't condone bullying. But in this case, the best thing you can do is let his brother and sisters rip the shit out of him. He needs the wakeup call that what he's doing is bloody ridiculous Grin

CowboyJoanna · 07/10/2024 14:13

Verbally I should add, not physically Grin

SophiaCohle · 07/10/2024 14:15

Autumnleavesareslippery · 07/10/2024 14:04

You’re spot on. A lot of people I know are very ‘be kind’ / fully accepting of this in children who are hypothetical and not their own. Having it explode in your own life also leaves the anxiety that maybe you’re not accepting about everyone leading their own lives as you thought you were. But it’s not a case of acceptance it’s anxiety for them, hurt from the parody of womanhood and grief.

Agreed. Careful with the "grief" word, which is a trigger word for TRAs, who will translate it for your son as "see, you're dead to them". And yes, balancing the screeching fear and worry for your child with the outrageous offence caused by everything they are doing and saying (also deliberately designed to provoke confrontation and eventually estrangement imo). It's a tightrope walk for sure. I wish there had been better understanding of the trans phenomenon a few years ago (I posted here and was given all the #justbekind crap) but I'm not sure there's any right way for individuals (i.e. at family level) to handle it without damage being done to someone, if not everyone. Feel free to PM if you want.

Runor · 07/10/2024 14:18

It’s some way back now, but to the poster who said you don’t have to be GC to be a feminist - how exactly do you talk about women’s rights if you can’t define the word woman? Yes, being GC is an intrinsic part of being a feminist.

OP’s younger children have clearly grasped the implications of gender identity for their own freedoms, and are rightly shouting up. OP, I think you need to support them to hold their own positions. I think it is ok to recognise that you can all hold your own opinions but still love and care for each other. Bearing in mind pp’s post about psychosis, I would also consider trying to meet up with ds at uni to try to gauge whether they actually need some more specific help

LittleMissViper · 07/10/2024 14:22

If you can open a dialogue with him, first thing I'd do is be asking what his aim is with all this. What is he hoping to achieve? And, more importantly, when will he consider his transition is complete? Hopefully his answers will give you some insight about why he's going down this path, and what his actual understanding about the process is.

It might be that you need to spell it out that there is no way to control the thoughts, beliefs and actions of other people. So if his ultimate plan and ongoing happiness involves everyone else accepting that he's a woman, then he's dooming himself to failure from the start, and setting himself up for a lifetime of misery.

Should it become apparent that part of it is that he likes dressing in and/or has a fascination with historical women's fashion, then there are many alternative ways he can explore and embrace that without transgenderism. He could get involved with theatre, or steampunk groups, or re-enactment, or live action roleplaying.