There is a time and a place for everything. It also depends if on the location.
If your at a T and A bar, then Go right ahead. If your in professional setting and you hope to continue your career, then maybe not.
Similar situation to you, but I had retired from my professional life, but still wanted some fun $$ and I went to work in a winery.
A 38 YO single mom went to work. We threw Digs at each fir a month, non sexual on in good nature. One day she was in a mood and I said to her "ohh you figured out my boobs are bigger than yours." She looked at me at me laughed, and said lets have a comparison.
We have been fuck buddies for months. Sometimes you just have to take a risk.