37 and 16 would not be a date probably considered a kidnapping.
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I am sure he asked to see her ID for proof of age before asking her out. /s
He was baiting probably the youngest one there. You say she looked 37?
IMO while working he could ask if she was going to college now?
Then she replies she might go to her high school prom in a year.
Minor chit chat before asking for a date in passing can keep you out of a lot of trouble.