Well lancer, sounds like this couple you met were displaying what my mum and I call northern humour, indeed the "would you like a cuddle?" is something I've heard before myself. It rather reminds me of the culture up hear in the north east which sees women being incredibly extravert, often quite sarcastic with humour and very often hard as nales, indeed one of my mum's favourite sayings is "don't argue with geordi women!"
It's nice in one way though since it means people are very down to earth and fairly straight forward, albeit other sides of it such as lack of compassion, often sterriotypes about men and homophobia exist too particularly when the people involved haven't had lots of education.
As to your massage idea, that might be possible if the person were male, indeed I'd probably be more comfortable with a large, intimidating welshman than a woman (especially a young woman), though again I don't know if I'd actually have the nerve to do that unless it was involved with some other activity such as muscle training or singing.
I've not heard of Wingman before (accept in that episode of the simpsons where Homer ends up being one), though again this is a miner problem since mostly anyone I would considder asking for this isn't around at the moment.
I did however last thursday complement a girl on her hair and gave it a stroke while my hand was round her shoulders during a bit of staging, so obviously things are moving forward slightly, that is indeed why I asked about bounderies since i'm never sure when trying that type of thing if it is too far or not.