In the 1st place, why the hell is he sitting in YOUR doorway? Let him & the kid sit in his own damn property FFS.
I can hear him now: "Oh, but little Samantha likes to play with these rocks/pebbles!"
That's when you bring out a gorgeous kids pail you've beautifully decorated, stuffed full of rocks & hand it over to him slash the kid & say, "Here you are!"😆

I mean, I'd be uncomfortable even without bringing *this* into it. Why is some old guy hanging around my stoop? Clear off, man, go find a playground.

Obvious ??, but can you maybe do some recording & get the cops involved?

I don't even like people smoking by my door never mind sitting in my doorway. I have told students to fuck off when they gathered outside.  He's too close for comfort. He's got no legitimate business there.  Is it communal doorway or sole use? Is it stalkerish to warrant a police complaint? If you weren't a SW you might not think twice about it.

But he'll be sleeping. Like I said, he is in a different building which is a across the street. I don't think he fancies me, he goes around sniffing everywhere like a dog looking for some scent. He just sits at MY door cause it's in a corner and the pebbles of course. And obviously he is suspicious of my scent and wants to sniff more

Exactly. You need to stop tiptoeing around this because it draws more attention to you - the normal reaction would be to go out and asking him why he's hanging around your home, point out that it's private property and tell him he's making you uneasy and uncomfortable so you'd like him to leave and not return.

Some weird creepy bloke hanging around outside a young woman's door and watching her from his car? I'd ask him once to stay away (and record yourself doing so, or at least note down the exact time and day that you did) and if he doesn't sling his hook then call the police and report him as a stalker. Twat.
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I'll try to muster up the courage to do this Amy, I'm very shy

Your private door! I couldn't work or live like that. I called the police on some workmen who were yelling like animals outside my window!...antisocial behaviour. I can't have clients snoozy massage disrupted by tradies shouting rubbish at each other. They were all questioned and told to behave right there in the street big daylight. I'm a right complain neighbour. We can't have people taking the piss, coming to your territory putting off clients or making it an unsavoury environment. If you're shy, a nice gentleman in a uniform will do it completely free!