Um… once, I think?
If by “official date” you mean “two people who aren’t in a relationship formally agree to go to dinner-and-a-chick-flick at a set time in an attempt to explore their sexual tension”… yeah, once. We had Mexican —or she did, I embarrassed myself by ordering a hamburger because I didn’t know what “fajitas” were— and then watched The Cutting Edge.
“Toe pick!” became our shared catchphrase for months afterward.