Many of us women over 50 are just starting to dip our toes in the dating pool again, and it can be kinda scary on so many levels. I figured a good place to start is by writing up this great resource for you of 90+ online dating questions to ask him, funny and serious. Look, dating at any age can be stressful, but when we’re in our 50’s and 60’s, oy. It’s beyond stressful.