There was such a service in Chicago in the 90s. I think it might have been more than $500 though (and that would have been in 1990 dollars). I don’t remember if

There was such a service in Chicago in the 90s. I think it might have been more than $500 though (and that would have been in 1990 dollars). I don’t remember if I saw the ads in the Chicago Tribune or the alt-weekly Chicago Reader. I’m not sure, though, that even though the good date being worth potentially hundreds of dollars would lead to most people being willing to spend those hundreds of dollars. When I was a young man, there was a lot of stigma about having met people through personals (the pre-app version of dating apps) or the early years of internet dating. I think probably the '00s was the peak period for social acceptability and quality of matches.