As seen in this Vintage illustration from Graphic's Fairy, a gentleman kissing a woman's hand appears to be a rather courtly, old fashioned thing to do. Which is why it's funny if you do it these days. Kissing a hand comes from the days when a man could only kiss the lips of someone he intended to marry.
Let's say you are on a first date and you are not one to invite someone up to coffee or a drink or into your bed so soon. Well, rather than a distant goodnight, or a formal handshake (which he may think of as "a handshake instead of a kiss" - a brush off) take his hand and give him one sweet kiss on the top of it.
Then swiftly, but looking back with a smile, go though the door - alone...
Flirting can include teasing.
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