I’m 26, single, and four years removed from anything resembling a serious relationship. So I did what any solo twenty-something guy would do: I installed Tinder on my mom’s phone and asked her to find me a date. As me.

Wherein our boss correspondent Michael Paterniti dons suits of plaid and bucks of white, drinks three martinis with lunch, sups greedily from plates of deviled eggs and London broil, takes his boys for a weekend of debauchery in a ’57 Chevy, wrings his soft, manicured hands—between sips of Sanka—over those damned Russians, and spends two weeks living as a man who hails from the year GQ was born…a time when men were men, and their wives did not like them.