The first time I saw You’ve Got Mail, I was cuddled up with a bottle of red wine several months after a bad break-up with a live-in boyfriend, and several months into experiencing everything the NYC dating scene had to offer a girl of 36.
I’d had a fling with the friend of a friend, who I trusted not to be shitty to me, because I was the friend of a friend, and then he was anyway. I’d been out on a date with a guy I met in a bar who picked me up after work in red convertible and took me to an expensive meal in Park Slope during which he sat very close to me in the booth, hanging with his arm around me through the entire dinner, and who afterwards dropped me at a subway stop. I never saw or heard from him again.
Then there was the guy, again met at a bar, who took me to see a soul-crushing arty film in which the protagonist commits suicide. Afterward he figured since he’d sprung for the movie, I really ought to let him take me back to my apartment and fuck me up the ass. And while I’m on the subject, there was the guy with the DVD porn collection that ran around the entire floorboard and completely filled a large floor to ceiling bookshelf in his living room who proudly showed me the “incest fiction” story he had written.
So, at that time in my life, everything about You’ve Got Mail appealed.
