This might sound crazy, but I’m going to ask anyways.
There’s a guy who is pretty well-known in the city I live in, and he’s the kind of guy I’d love to date and get to know better. He is single and has an occupation which means he is in the media frequently, but he’s close to 40 and has expressed his desire to meet someone and start a family. If he was not well-known, I’d approach him without thinking about it (like if I saw him in a bar), but I am unsure of whether I should ask him out given the circumstances, and if so, how? I know the location of his workplace (it’s public knowledge), but he would have an assistant or someone monitor letters, emails, social media, etc. I see him in person from time to time, but it’s hard to get him alone to ask him out or slip a note with my number. I thought of sending him something with a note and my number, but I’m not sure if that would come across as creepy.
I am personally a low-key person but would have the confidence to ask him out if I got the opportunity to do so in person, but it’s hard when he’s always surrounded by a crowd. I figured the worst that could happen is that I get rejected, which I am willing to accept.
