Cloudsurf,
I deeply regret not having done the same around 6 months ago. I was on a Seeking Arrangement date, and got to the restaurant around 45 minutes early, before my date, wanting to have a few drinks at the bar. The bartender was a smoking hot college student, racially mixed girl, looked hispanic mainly. We chatted amicably about her studies and interests for a while. At some point she noticed I had a gift bag on the empty barstool next to mine, and asked me if it was someone's birthday. I just said "no", and steered the conversation elsewhere. Later on, I played the conversation back in my head, went into Cloudsurf mode, and heavily regretted not having taken a shot by simply telling her I was on a Sugar Daddy date and asking her if she had ever been on one. If I had been thinking properly, as I should have been - as a professional client, so to speak - I would have done it. It wasn't that I lacked the nerve, I just did not do a good job thinking on my feet at that moment. I did go back to the bar a few times looking for her but never saw her again. I think she was working an odd shift for someone else. I may take another shot this weekend but she is probably gone from that job. Sometimes you gotta take a shot in a situation like that because you never know what will happen and you have nothing, nothing, nothing to lose by asking a girl if she ever went on a SD date. Worst thing that happens is she says no and ends the conversation there.