Blind Item #12 - Lipstick Alley Blind Item

I'm 28, and I've been casually involved with a famous 55-year-old musician for nearly a year. We crossed paths randomly in my city, and we catch up every now and then. I enjoy our time together, and it's clear he appreciates spending time with me, both socially and intimately. Despite our connection, financial support hasn't been part of the equation. We share nice dinners, vibe at his place, and he's even introduced me to some people in his circle who seem to appreciate me. Interestingly, he has children my age.

Now, I'm contemplating whether it's time to distance myself, even though I think there might be more benefits beyond just companionship. While I'm not looking for a romantic relationship, he's a nice guy with access to a vast network. With aspirations to start my own business, I've considered approaching him as a potential angel investor. However, there's this nervousness about being perceived as a gold digger. Over the year, we've hung out about six times, and we stay in touch regularly. Last year, due to my busy schedule, our meetings were only occasional. though he is wealthy he is smart with his money and not flashy. However I’m upset he didn’t get my a Christmas gift lol but he wants to see me this week and I might bring it up.

I'm not inclined to completely cut him off, considering his strong connections, and I value maintaining a friendship. I want to benefit from this connection beyond intimacy. When he was tipsy once, he mentioned supporting my passions. He said this in front of his friend and it could have been hop showing off.

Despite my reluctance to ask for help, he consistently jokes that I'm a future CEO and expresses belief in my potential. He is drawn to me because I am very independent and successful but I wonder if I should have played broke and dumb when we met.