A side thought ...

I also wonder which parts of womanhood he identifies into (slinky clothes, make up, ladies toilets) and which he ignores (the drudgery work of keeping a household and family running)

Yep. 2nd wave feminism in a nutshell

There are non-misogynist men who work hard on treating the women in their lives as fully human. He could try to be one of those. Saying ‘I’m a man who challenges toxic masculinity’ can be powerful, rather than ‘I hate toxic masculinity so I’m going to dabble in (stereotypes of) womanhood.’ In any case, he can’t change his sex, no matter what cosmetic changes he makes. And if he goes ahead, he really shouldn’t want lesbians to date or sleep with him because he’s a ‘fellow lesbian.’

I agree with this.
In addition in certain areas of youth organisations there are some amazing opportunities for girls and "people with diverse gender identities".
It pushes the benefit of not being a male who is trying to get comfortable in their own skin as a male even further.

And what he feels is ‘feeling like a woman’ can only be ‘feeling like how a male fantasises what it would feel like to be a woman’

My conclusion: Sorry, I don't buy it. It doesn't add up and is far more likely he is motivated by sexual gratification than a seriously misplaced attempt at being a better person.

3. If he thought men were dicks, you think he might just try and be a good man to women. It doesn't take very long to realise that the trans movement is hugely detrimental to women, and a super toxic environment for men. It is entirely about eroding women's boundaries. So I don't think he can be that motivated by his care, not really.

point 2) women are not inherently better than men, there are toxic women as well as toxic men it just presents in different ways. There are lots of fantastic, honourable men who we need in this world. He could be one of those.

I'd guess he is AGP but it much easier to tell his mum that 'I want to be a woman cos women are nicer', than 'I am sexually aroused at the thought of being a woman's and I want to wear women's clothes all the time now '

He might think he "doesn't feel male," but he can't "not feel male" because "male" isn't a feeling.

Op, I could see your point had he been 14/15/16/17.. There is a point at which teenage boys are treated quite differently as they venture out into the world than girls and it can be a shock to the system when they've been treated roughly the same as children up to that point.
Maybe combine that with not quite fitting in with your male peers and trying to work out why and you might get a teenage boy who is confused for a time.
The cruelest thing society does is let these young people think they can opt in to the other sex.

However he's 27 and has had time to move through that phase.
Surely if he doesn't want to be one of those men, he also doesn't want to be one of those different men who say they're women and go into women's spaces and scare them.

Can you give him a copy of Robert Webbs book? He's a good role model for men that don't like all that comes with masculinity.

I have a DH who gets on better with women, female friends all through life, close to his sisters, happy in his own skin. Similarly my DS (10) has a gang of friends which is 4 girls and one other boy.

He will be much closer friends with women if he isn't making himself the centre of things, making them play along. Can he maybe join some hobby groups or something to make friends, then they'll have a common interest beyond gender?

Some of us have been outraged for about a decade about men pretending to be lesbians.

The one point that the OP is making is the one that is being responded to.

That was the side thought. If I raged against every single post regarding men and their vile encroachment onto lesbians I'd never get anything else done. As it is relentless. And going for lesbians and not just straight women is part of the thrill for them.

Isn't this pretty much the same argument as used by our recent visitor - the one who, before flouncing, posted across multiple boards, claiming women were nicer people and that we should be flattered?

This.

All he's doing by trying to be a "lesbian" is massively limiting his potential dating pool.

So you and his mum have brought him up to believe that men are awful and women are much better? No wonder he doesn’t fancy being male.

Could you not work to redress that? Apologise for giving that impression, assure him
men can be fabulous and he has that opportunity! He can be an amazing young man who respects and values women.

He can’t be a woman, and he mustn’t ape womanhood. Him swanning around ‘being a girl’ is like you swaggering around in low hanging jeans, swigging beer and belching because you don’t want sexist people to patronise or overlook you for being a woman

'why this young man seems to feel a need to identify with women rather than with “good” men.'

That's the question to ask.

It seems to me even worse.

A white person demanding to be recognised as black is not expecting (and backed by a political lobby demanding) that anyone else must validate him by providing their body and unpaid sex work.

There are plenty of bi women who are attracted to men of all gender identities, there are (waiting for the inevitable arrival) women who will call themselves 'lesbian' because they see it as an identity to choose and who will happily (say they) date male people of various identities including TW. The issue will be that a woman who says no, she is homosexual thanks, exclusively attracted to biological females only, and can perceive a male in any presentation and does not want to have sexual relationships or romantic relationships with anyone other than a biological female? Will be told she is wrong, a sexual racist, and she must 'learn to cope' with straight sex rather than deny her body to a man who wants to use it for his validation and will have his chosen sense of self jarred by her expecting to be treated as an equal human being as opposed to a walking sex toy. Or say to want sex to be something she enjoys as opposed to provides through gritted teeth with tolerance of something unpleasant being the most she's supposed to hope for.

No other group is required to not only pretend that men are something other than men when they say so but get their clothes off and validate said men in their identity by showing nudity, peeing in earshot/close presence, accepting intimate processes regardless of distress such as breast exams, smears and post rape examinations, and provide their body for sex. Only women. And especially the women who say no, because forcing access to them is the golden ticket of validation of chosen identity.

And as pp says: when you see the men and their women enablers descend on female homosexuals trying to meet, because how dare those women gatekeep their bodies from men wanting to use them? You realise how sociopathic and evil this is.

Why anyone would indulge a man in treating women like this and make excuses defeats me. Sympathy can only go so far before you are actively enabling.

I think the idea that women are inherently 'better' then men is damaging to both sexes. Women are human beings and as such we are as prone to flaws as men are.

For sure there are differences in behaviour, e.g. less propensity for violence and sexual crime we don't fully understand. We are still fully human so please ask your friend's son to stop treating us as plaster cast saints. It's insulting to decent men and also an image that no woman can live up to.

As for your feelings towards this person, it's perfectly possible to have a soft spot for someone and think their attitudes and behaviour are delusional, entitled and predatory.

Just imagine if someone went onto a BAME chat group and talked about how her friend's son identified as BAME even though he was white. And how lovely that was and it was because of a lack of decent white role models.

Then the natural reactions were described as 'hostility'

I fail to see how identifying as a lesbian if you're a man is any less offensive.

@LindorDoubleChoc i have just re-read your OP and am unsure what your friend means about her son. Is he identifying as a woman as in dressing like a woman and trying to “present” as a woman? Or does he identify as a woman as in being a feminist and feeling uncomfortable with “laddish” behaviour?

Yes, I agree with pp that this young man is probably laying on the flattery about women pretty thick and his mum and the OP quite naturally want to think the best of him so they are inclined to believe him - maybe he even wants to believe himself, but that doesn’t make any of it true or acceptable.

It’s the TRA version of the nice guy isbt it

“I’d never be mean and aggressive and nasty, I’d never send abusive messages and shout suck my dick. Im
a nice guy, I love women, women are so much better than men. Also suck my dick.”

it’s still the same level of male entitlement and only seeing women through the male gaze as support humans not real people.

It's just breathtaking narcissism and entitlement to just decide you can be a trans lesbian (or whatever) and not spend 30 seconds considering the feelings of lesbians. Well, of course, maybe he has considered and decided he doesn't care about their consent.

He appears to have absolutely no capacity for empathy at all nor see women as fully human. This seems to be a feature not a bug with men who transition.

I'd recommend reading the transwidows thread, and it might be useful for this man's mother too.

There's lots of non-toxic men out there. The violent criminals take over the news. The toxic, abusive ones take over this site but the majority of men are nice, normal people.

I fundamentally disagree with men escaping into "womanhood" as a refuge from masculinity. Women are not support humans for men who don't like other men. We are not a refuge for men.

If men don't like the way men act or think then they should bloody well fix it. It's not up to women to solve men's problems. We're pretty busy trying to work out how to fix our own.

The mum of this man is of course sympathetic to his pov, as are you OP, you've known him since he was a child. Tbh I would put money on some kind of transvestism/AGP being involved. Being distressed at toxic masculinity does not typically lead men to put on dresses.