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This past week, with the re-release of “All Too Well,” many people were wondering how Taylor Swift got her heart broken by Jake Gyllenhaal after only dating him for three months.

I was not one of these people!

1985. I was working at a store in Boothbay Harbor, Maine that sold puppets and clothes. I met a guy who came into the store. I think his name was Bobby? He was a freshman at some fratty school. I made out with him on a dock and he gave me his Swatch and wrote me a card that I still have that was actually pretty long for a guy writing a card. I wrote him back. Nothing. Talked about him every day of junior year, read the card over and over, looking for clues of our demise.
1989. Sophomore year of college, went out with extremely good looking guy who had just graduated and had a real job and everything and lived in the next town over, which seemed incredibly sophisticated. I have a vague memory of him telling me I was a boring lay…not in so many words, of course, and he wasn’t even trying to be mean, but honestly, I was 19, so, what do you expect? I read his journal one day. It said, “I like Sarah but I don’t love her.” I didn’t ask him about it but I broke up with him, saying “I just don’t think you’re that into me” which he confirmed, having no suspicion of what I had done. (I thought that was pretty crafty of me!) Talked about him incessantly for at least a year, main source of my complaint was that he was still in love with his ex who I thought was objectively less attractive than I was, it seemed impossible to me that things could work this way. I ran into him at a bar on the Upper West Side in 1992 and made a complete ass out of myself. He’s a doctor now with very mixed reviews on Healthgrades.
1995. Met a guy who went to grad school with my friend. I was absolutely convinced he was it for me, my “person.” We kind of hooked up once. Barely. He told me he just wanted to be friends. Was friends with him, sort of, kept thinking he liked me, he didn’t. In complete and utter anguish over this for at least a year, tortured mutual friend analyzing him to the point where she screamed at me over a pool table, could not understand why. Ran into him in a restaurant in Silver Lake in 2002, made a complete ass out of myself.
2005? Was out of town and met a guy, friend of a friend, talked to him for mayyyybbeeee ten minutes. He was married. Somehow became convinced that we were made for each other, seemed mutual, in retrospect probably was not though he was very responsive. Anguished 48-hour correspondence, one short meeting, some more correspondence, maybe a day, and then another day of one-sided correspondence (me) as he realized not only that this was perhaps not a good idea, but also that I was not, and I’m being generous with myself, in a good place. I was such a mess that the guy I was living with at the time, and in the process of splitting up with, actually felt sorry for me. “You poor thing,” he said when I got home. “Why don’t you just take to your bed for a few days.” He meant it. I did. Felt like my life was over for longer than I care to admit, was also horribly embarassed, which, as Taylor Knows, is the one thing you never get over.
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The Real Sarah Miller

Four Times I Was Heartbroken From…