I hand pollinated two budding squash fruits last week because I was worried the male and female flowers would not pop open at the same time. You can't count on the bees or other insects to pollinate, especially these days when there aren't a lot of natural pollinators around.
Hand pollinating squash is easy to do. Carefully strip the petals of the female blossom, doing your best not to touch her stigma. Then strip the petals off a male flower, taking care not to spill any of his pollen. Now, dab the pollen onto the stigma. If you don't feel confident that the male had sufficient pollen, then pick another male flower and repeat.
The summer that I was 17 I worked as a hand pollinator for a seed research company. I got the job purely through nepotism. The Mama was in charge of hiring summer help who were usually teenage girls. She waited until I graduated high school before she hired me. She also hired my friend Kathy, who let the Mama know on her last day on Earth how much she appreciated the Mama for giving her that job.
I enjoyed the job and having the Mama as my supervisor was no big deal. She treated me like everyone else, expecting no less nor more from me. Her instructions were clear and no-nonsense firm. She must've been impressed with Kathy's and my work because a few times she sent us off to the cages to pollinate the cabbage, which required very steady hands to manipulate tweezers to strip petals away. About halfway through the summer, she let us change our hours so we got to start work an hour earlier before she and the others came in. That was trusting of her, come to think of it.
Yeah, I think the Mama would be surprisingly pleased that I still know my hand-pollination skills and that I'm using them to help the squash grow in our vegetable garden just like she did in hers.