To end friendship because I can't stand her husband?

I've already brought it up with the headteacher and she spoke to friend (now presumably ex friend) and apparently "She's fine, don't worry!"

You can tell the difference with a modicum of reflection.

If it's just that he doesn't do small talk or take hints, that's ND.

Controlling or insidious behaviour is different.

Exactly. If you want to make individual plans with her, make it clear it’s her you want to see, and that it’s not a child occasions — suggest an after-work drink or something.

He could be any one of those things and OP can still have an opinion on whether she finds him creepy and whether she wants to spend time with him or not.

We're told to trust our instincts - but we're supposed to make allowances "just in case" he's not creepy he's just NT?

I told my sister I don't want to spend my free time seeing her husband. It's just not the same having a man hanging around. Now I say are you free to meet if he is off we just don't bother

She obviously doesn't see you as a friend, just a mum who's kids play with hers. She's sending him, to ensure the play date goes ahead! I had this with another mum too. He was working lates and she worked long shifts, she always sent him for play dates and he'd always stay with me. I find this werid and creepy too, I stopped asking and she never followed up! Just stop arranging things. If she reaches out I'd honestly say, "I'm sorry we don't meet up anymore, it's because you're never available and send x instead! If I wanted to see x I would have arranged it with him."

Her sending him on the play date with you and the children is interesting. It suggest she has no idea that a key reason you want to meet up (apart from the children) is your friendship and camaraderie. If she’s not getting that, then she’s not the friend you think she is.
You say he doesn’t seem controlling, so I think in your position I’d bow out. Slowly be less available. If you’re keen to keep her, you could try suggesting girls nights out to see if she understands this means, not him, but I get the impression he’d still somehow tag along.

I’d sack this off if I were you. You don’t need to justify it really, he makes you uncomfortable and their dynamic means he’s always about. It’d be a no from me.

I agree with PPs OP, this woman doesn't think you're friends, she thinks your kids are friends and all meet ups are to facilitate their friendship.

Anytime you meet up make it clear just say 'girls dinner' or 'girls coffee' she'll get the message without having to have that conversation

This is chilling. I'm really pleased that you're making sure you're never alone with him, he's escalating.

I’ve been the friend with the creepy partner that everyone stopped talking to…. I was so controlled I couldn’t see it at the time until a light bulb moment that lead to me having him arrested. I wish some of those people had stuck around in the shadows because coming out of an abusive relationship with no support is really hard.

keep the contact minimal if you need to but don’t walk away because one day she’ll see the light and she’ll need people to help her keep going forwards. Because if the option his him and his abusive ways or nobody at all it’s too easy to go back to him thinking something is better than nothing

I have 2 friends who have ended up with awful men, I mean truly obnoxious. The friendship ended with one because I did point out his abusive behaviour. The other one isn’t in an abusive relationship he is just a tiresome thick individual who has some really ridiculous opinions that are not well thought out and drones on about absolute bollocks. I see a lot less of her which is a shame but they are also glued together or so it seems.

I also had a friend with an obnoxious child, they became an obnoxious adult, it was a shame. But when your family also don’t like spending time with people and it’s not just your own thoughts then it’s over.

Pound to a penny he has her phone.

Yes - by the sound of it, he's not actually doing anything wrong.

From your update, it's your children who are friends. She doesn't see you as a friend, it sounds like.

She is disrespectful and a boundary pusher. I was in similar situation few years back and it turned out that my so called friend and her husband wanted a threesome with me. So her husband was behaving exactly as you have described. She would send him instead of her, he would pry on my private life, make inappropriate jokes. She told me later that I was his type and they were into different things to keep their marriage spicy. Nothing wrong with that but not at my expense. We are obviously not friends anymore.

I wouldn't give that a second thought.
I would 100% stop making any effort.

Unbelievably rude to not turn up and send her husband, even if you liked him.

Unbelievably rude.

Make no further effort.
If asked tell her you don't turn up, send your husband, which is really rude.

Or say nothing except no thanks busy.

She would really piss me off.
So bloody rude.

Actually I would find her very controlling and creepy to do that.
She is dictating your time and company.
So dishonest of her.

I've read your updates and the ‘creepy vibe’ sounds less creepy than someone who maybe finds some life stuff hard that you don’t. His DW sounds like she’s trying to get him out and about perhaps. I get that you may not want to see him in the same way as you want to catch up with your friend and you can just say you prefer girlie time etc.

After your update, it doesn’t sound like youre friends, it sounds like your kids are friends.

If she works and he doesn’t it makes sense that he would be the one taking the kids to play dates etc.

If you want to see this woman without her husband start making plans that don’t revolve around your children.

This does sound odd to me. Your instinct has kicked in re the ‘creepy vibe’ and I do find it a strange that he’s always there when you meet save for a few occasions. I’d expect it to be the other way around. My friends rarely meet with our DHs around save for maybe the odd party/dinner etc. Or if my DH is at home he’ll do some chit chat and then disappear so I can have time with my friend. His behaviour sounds deliberate and controlling. I’d suggest finding ways to get her out of the house to meet but I’m guessing maybe this is hard as it’s not happening that much.

So she went to Aldi instead of meeting you and sent her husband in her place.
I don't think the husband is the problem.
You think she's your friend - she does not feel the same way about you, sorry.

This. It doesn't seem like this man has done anything actively wrong except being perceived as "odd" and "creepy".

He could just be socially awkward, neurodivergent, can't read social cues or have other issues that affect his appearance & mannerisms which aren't related to wanting to do anything evil or creepy to his wife's friends. ND people are often disliked by NT people without a solid reason.

If he made inappropriate comments or his wife has hinted at other things then it makes sense. But to start a thread about a man who seemingly did nothing wrong except "look odd" is pure schoolgate gossip.