What was the most intrusive first-date question someone asked?

How many people have you slept with

Why did your ex dump you?

Was asked about my financials. How much is in my savings and 401K

Nice smile, great sense of humor, calm and collected…do you have any extra anti-depressants?

We met in a very upscale suburb on first day he asked me if I was old or new money

paycheck is specifically after taxes

Have you ever had to visit a therapist? Or do you have Daddy Issues?

Why did you ex dump you?

He was a cop who looked me up and asked why I decided to shoplift when I was sixteen

He asked if i slept in the nude or in lingerie? Weird.

While on a lunch date with a car salesman, he asked “what’s your favorite position?” I played dumb and answered “shortstop.”

Is your personal balance sheet heavy on the liability side…?

“Whose ring are you wearing? Maybe it will be my ring on your finger soon!” (This was a first date!?!?!)