first date and she wears this

That probably means you should've asked her to watch a Netflix movie at your house rather than out to a heavy dinner

There's a sense of humour there. I just can't decide if it is my kind of humour.

So..... what's the fucking problem?

that's a red flag. A high sugar diet is most certainly precursor of health issues.

Later that night, OP is tied up to a bed, completely naked, then the charmant lady enters the room wearing a full clown costume and face makeup just to smash a massive creampie to his face.

Well then good news - we're eating at Baker's Square!

....mom?

Typical