Man on school run

Resting murderous face? It’s a terrible affliction.

My thoughts exactly!

Under no circumstances would I approach him.

I would completely ignore him. He sounds like a nutter. Its probable that he know what he's doing and will continue to do it, I wouldn't engage with someone like that.

At pick up - I would wear dark glasses so he won't get any further opportunity to see you if you happen to glance in his direction.
I would make a point of blanking him and just completely ignore.

Not to pick holes or anything, but feeling someone's eyes on us when we're not looking isn't something I'd describe as precious. This instinct has been hardwired into humans across many millennia. It's there for self-preservation and designed to ensure our very survival. That's the reason every single one of us is familiar with that feeling: evolution in action.

Same thing goes for the gut instinct. Maybe this dude is a creep, maybe he does it to other people as well, maybe he's just naturally nosy, maybe he's just nothing at all. Whatever he is, he's making OP uncomfortable and it's a pity women are the ones who have to risk-assess all the time, even when we don't necessarily know we are doing it.

One to avoid where possible, OP. I see that this is difficult, but school drop-off is fortunately a short-lived commitment.

I agree. You have to be looking at him to notice he is looking at you so much

He may be just one of those men who enjoy intimidating women.

This. ^ just don't look at him @Frisps ! Not that hard really. OR go to a different place to wait for you DC. If he follows you and keeps staring (and following you so he CAN keep staring,) then confront him then. Ask him if he has a problem with you.

Well you've been watching him enough to have noticed what age his DC, so perhaps he thinks you're the strange intrusive one. Especially as you started off smiley.

It's normal to look at people as they pass you. And if he's always looking intense, it's probably just his resting face.

Perhaps if you stopped looking in his face to see how his eyes are, then you'd find it easier to ignore him (and he could keep on ignoring you)

I would have to ask the next time we made eye contact ..."can I help you?"

I agree with @Mazuslongtoenail that I might well stare daggers at a mum whose child was nasty to mine.

Could he possibly know you from a different context such as your job? He could be one of hundreds of customers, so he recognises you but you don't know him from Adam.

Perhaps you remind him of someone and he is trying to figure out who? Or he knows who and he hates them?! Do you drive an SUV? Lots of people find them annoying and excessive.

Can’t you just ignore it?

Definitely confront him and ask another school mum to come with you while you do it.

If you're going to confront him at all - and I don't know whether or not I'd bother or file this away under 'small stuff' - then the way @anarchicparadise suggests above is the way to do it. That, or grin and wave cheekily to him, and move on.

I'm not sure why so many people, when confronting someone behaving a certain way toward them, ask what it is they've personally done to prompt that behaviour.

Don't pick up their baggage or internalize their shit. This is his problem, not yours, OP.

Can't you just ignore it? Surely it'll stop if he's not said/actually doing anything to you. It's not worth worrying about. At least I wouldn't, anyway.

He might have mistaken you for someone else. I agree with others. Smile widely to make sure he doesn't just have RBF (he should return the smile) and if he doesn't say 'do I know you?'.

If you are worried about him sound this out to another parent in case he has history of being aggressive.

Laugh at him. Next time he makes eye contact burst out laughing at him.

Honestly, I doubt very much he is glaring at you. I mean, why would he?

My first thought too. Either parking like a knob or a child who isn’t nice to others would be my dagger stare reasons.

He might be extremely short-sighted and be totally unaware he is looking in your direction. Saying you can feel his eyes on you when you're not looking at him sounds a bit precious to be honest. I would walk up to him and ask him why he is looking at you like that, but don't be surprised if he's taken aback and doesn't know what you're talking about.

Making eye contact is normal. How do you know it's him passing your window to "feel" his eyes? You're also looking at him!

Just say a cheery morning!

I was thinking this too, you seem to look at or notice him a lot. It’s probably his natural resting bitch face and he’s wondering why you keep staring at him

I would ask him, but first I'd want to be really sure that he is glaring at you.
Is there anybody at the school gates that you could ask to discreetly look out for him, and get an opinion from them if he is really looking at you angrily - i.e. it's not just his usual expression?
Or bring a friend along who would observe him from a distance?

You only have 2 choices as far as I can see.

Ignore him or speak to him.

OP this is your chance to put him in his place.

”Hi, sorry do I know you? Do you know me? Why are you drawing me daggers?”

be forthright.

I'd completely ignore him. It's either his resting bitch face or he's ND and doesn't realise he's doing it. Or he's being a total cock for some reason. The best way of dealing with both scenarios is to act completely oblivious.

Perhaps he's noticed this strange woman who keeps looking at him ?

It might be his resting bitch face. Can you sneakily have a look when he's far away and see if his face appears different when waiting for his child to come out? I look permanently grumpy even when I'm interested in a conversation/person.