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Meeting a SD in the wild..
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I always thought this was impossible especially because I live about an hour and a half outside of a major city. But I have this gentleman who comes into my restaurant about every other weekend (he lives in a bigger city during the week, but stays in his second home here on most weekends. I’ve started to get to know him pretty well, and we have long conversations when he comes in. He definitely has money. He is attractive and in my preferred age range. How do I approach him about taking him and I outside of my work? And then, how do I approach a sugar situation from there? Or do I?

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2 months ago