Over in Alexandria, his date, Ivana Hampton, 41, also worried about how she was presenting herself, having never had a blind date or even an online date before. She stopped at her mom’s house for a last-minute wardrobe check. “Why are you wearing that?” her mom questioned.

“She thought I should wear a dress, but I wasn’t feeling a dress,” Ivana told me. So she kept the pants and ordered a car to Matchbox in Chinatown, arriving about 15 minutes early for the date.