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It makes zero sense to even consider a move like that unless the two of you are in love and want to make your relationship a top priority. He sounds very confident, so if he is interested he will pursue.
I have a friend who just likes "messing" with me but also likes making me laugh. He likes sitting behind me and touching my hair or sitting beside me and putting his hand over my chair. Does that mean he really likes me or is just flirting and toying with me. Prostitute Renmark
In more traditional relationships, boundaries and expectations are more clear cut. So how do you negotiate your way through this potentially difficult and dangerous dating minefield where one person is handing over potentially large amounts cash to the other. How do you stay safe - presuming your Daddy turns out not to be he claimed to be.