Dear Quentin,

I’m a 35-year-old who works in IT and gets paid a healthy six-figure salary ($140,000 a year). I live in Chicago and date a lot. Over the years, I’ve been on Tinder, Match, OKCupid and Bumble, and when I tell you I’ve had a lot of dates, I’ve had a lot — maybe 40 or more in the last couple of years, although not all for dinner. 

I…