Dating my mentor’s daughter?

I’m male, 26.

A few years ago I did a lot of videography work for my mentor and during that process I was introduced to his daughter who is a beautiful and successful entrepreneur with an incredible heart and I genuinely was crushing on her from afar, but I didn’t make a move partly because of a lack of confidence and partly because I didn’t want to jeopardize my relationship with my mentor. My mentor and I are still on great terms and I filmed his son’s bar mitzvah last year where I saw this woman and I was nervous again so I left her alone.

Recently I have been doing a lot of internal growth and made several permanent lifestyle changes which have improved my confidence (dieting, meditation, achieving entrepreneurial goals of my own, etc). And this week I started a YouTube channel about mental health to talk about my recent growth, something I’ve been wanting to do for years. I was thinking about ideas for videos and remembered that this woman’s company is all about mental health.

Back when I worked with her dad she had asked me to make some videos for her company but she didn’t have a budget and I declined to do it for free. Now, not only do I want to do the videos for free and to genuinely support her initiative with no ulterior motives, but I’d like to see if I could get a date with her to see where things might lead as well, since I think she is a very charming, attractive person and I want to know her story.

A few things: I’m not sure if she’s single, I’m pretty sure she just sees me as one of her dad’s colleagues and doesn’t have similar feelings, I still don’t want to jeopardize my mentor relationship, and I don’t want her to think I’m creepy/seedy or have the wrong intentions for either the date or for the project.

My question is: when I contact her, how should I approach it? Should I mention just the project first and the romantic interest later if she’s interested in the project? Vice versa? Both at the same time? Also with COVID going on, is dating even a thing right now? (I’m in MA)

Cheers, many thanks and happy early 4th! ???