I know a number of trans people. I have had a very honest conversation with one about certain things. He knew my position before he transitioned. It was healthy and productive for both parties.
The idea that you can't be friends with someone because you have different views is alien to me. I will happily talk to and socialise with a very wide range of people. It's healthy and you learn stuff.
Where I have a problem, is where people don't respect your position and think it ok to bully you and try and guilt you.
It's not so much about beliefs. It's about behaviour and wanting to impose / control others.
One of the problems with trans activism is it has a lot of people who support it who actively work to bully, coerce and shame and say this behaviour in others is ok.
It's not ok.
It's about behaviour not identity.
There are a great many women on Mumsnet who have child, partners, siblings or parents who have transitioned and have experienced emotional abuse and they have no where else to express this because they are automatically labelled 'transphobic'. That's just not right. No collective group is perfect.
The trouble with trans identity is that this pattern of behaviour is actively encouraged by the politics surrounding it - so there's no way to easily challenge unacceptable behaviour. And because of the politics around it, it now actively attracts men who find the ability to do this under the protection of the shield of guilt and shame. So it's become very much a toxic bubble.
As I stress the problem is NOT about identity. It's about behaviour that would be unacceptable in any other situation.
The litmus test here is "if a woman did this, how would I react". If you are treating a trans identifying man differently to a woman, then they aren't living as a woman. Equally if a woman did the same thing and you wouldn't tolerate it, then you don't tolerate it because of the super shiny cloak of 'bekind'.
I'm willing to bet, the OP doesn't go on shopping trips with her besties. So why is she compelled to suddenly do it for this man? It's forcing the OP to change her behaviour to match the mans social expectations of what women do, when it's not true.
And there is a reality that no matter how kind you are, they never can change sex. This creates a problem because many develop a dependency on validation from others to compensate for that and being constantly reassured that they are women - whilst at the same time, women are not allowed to be honest and say
"well actually since you are 6'2" and shaped in a particular way, it doesn't matter what advice I give you about clothes, make up or hair you'll still never pass. I just wear what I like and feel comfortable in and that's why I wear jeans and a t-shirt and frankly I've never bothered with makeup because it ruins your skin".
A true friend would say that. But because of the dynamics which the ops friend is displaying, it's clear he's not going to want that and respect that. So he's already driving a bulldozer through the friendship, not her. Someone who wants a friend to merely be a yes man (or woman) isn't displaying healthy behaviour.
We need to recognise that women saying "no" isn't hate. It's not being unsupportive. You CAN be supportive but it mustn't be at the end of threats and relies on mutual respect. If a trans friend values his friendships he needs to understand that the women around him are allowed to be honest, critical and say no if they feel it's appropriate and it's not because they hate or are transphobic. It's because they are treating them like they would anyone else and they are still able to say "stop being a twat and an emotional vampire" if appropriate. Being supportive is NOT being someone else personal bodyguard nor is it being their therapist.
And it STILL doesn't change the point that you can't change sex and women are LEGALLY allowed to have a boundary based on their biological sex.
The fact we CAN'T have this conversation IS the ENTIRE problem.