All posts filed under: Dating

How to Date Your Crazy

By Ruth Gallogly

I should have known we wouldn’t work out when I messaged him one of my favorite quotes from Alain de Botton. It’s from the On Being podcast “The True Hard Work of Love and Relationships.” In it de Botton says the question we should really be asking on first dates is: “How are you crazy? I’m crazy like this?” “I don’t get it,” he replied via WhatsApp. “How do you ask about crazy?” Of course he didn’t listen to the podcast to find out. I let it pass. He was sweet. He was cute. He was smart. He had his career together. I took this to mean he had his emotional life together too — all of it nicely bundled in a cultivated gift wrap and tied up with the sexy bow of an Australian accent.  We matched on Tinder two days before he moved from New York to Colorado, and when we couldn’t work out a meeting before he left, I figured he’d disappear. But he didn’t. A month after we connected, he flew …

Before We Ever Met, He Tattooed My Name on His Hip

By Lu Chekowsky

When he got my name tattooed on his hip, we hadn’t met yet. He was 50. I had just turned 30. He had a big job in the city at a law firm, lived on Long Island, and wore tailored suits to work. I assumed he was rich. He sounded rich. I was working as a telephone dominatrix from my ramshackle apartment deep in Jersey City and had just filed for bankruptcy. His voice was measured, wise. I liked him more than the others and more than I was supposed to. My voice on the phone, was confident, lulling — often just a whisper. It was one of my trademarks and how I controlled them. I was good at it. The other women on the line thought the guys would spend more money on you if you yelled at them. They were mostly wrong. One of my best clients, a shy music professor from England who had six pet rats, left me five stars and this comment on my site one time: “I’d sell my …

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The Story of the Guy Who Crapped in My Bed

By Judy McGuire

I knew he had a girlfriend, but that didn’t stop me from liking him, nor did it discourage me from making out with him at any opportunity. He told me all the old standard lies — she was a bitch, she was crazy, they never had sex anymore and they were pretty much dunzo anyway — and I chose to believe him. Sigh. Yet due to some sort of highly flexible boundary system he had worked out in his head, though we would fool around, we never actually had sex. Because somehow being handsy and mouthy was fine, but actual p-to-v would be cheating. Sigh times a thousand. Maybe it was because I had been single for so long, or dating jerks, or catching a case of the incredibly stupids, this went on for some time. I lost sleep, moaned to my extremely patient friends, and basically acted like a complete asshole. “He’s so nice,” I’d bleat, savoring the little crumbs of affection I’d collect whenever we’d manage a few minutes together. Like every other …

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My Very Public Online Fling

By Neil Kramer

After my divorce, I was as broken as a tree branch after a storm. Luckily, I found a female comrade — on Twitter of all places — who was healing from her own divorce. Our digital friendship blossomed into a long-distance digital romance. We sent corny notes to each other on instant messenger and kisses over Skype. After a few months of online communication, Cate (not her real name) suggested that we meet in real life. One caveat — she lived in New Zealand. After much thought, I decided to seize the day and off I went to catch my Air New Zealand flight. The exterior of the plane was decorated with characters from The Lord of the Rings movie, which was filmed in New Zealand. Like Frodo Baggins, I was off on an adventure.My trip to New Zealand has all the elements of a Harlequin romance: Cate was beautiful. New Zealand was stunning. The clouds were as white and fluffy as cotton; you wanted to grab a piece from the sky and feel it …

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Mr. Knightley Is Not on Tinder

By Lisa Wood Shapiro

Newly single, I have, at the urging of friends, downloaded dating apps on my iPhone. On more than one occasion, I’ve found myself in some dark hole of the internet and wondered if I was an unknowing participant in a secret Cindy Sherman project where she’s disguised herself as red-eyed, heavily jowled men sitting next to sedated tigers or at the finish line of Tough Mudders. Those first few swipes felt odd. Throw in a married dad from my son’s elementary school and a few minutes of swiping left made me want to wash my hands. I’ve been guilty of having a few laughs at the expense of these dating prospects. I’ve screenshot their most awkward profile photos to share with friends, and I’ve attended Lane Moore’s Tinder Live Show. When I was first single and my friends would ask me what I was looking for, I would tell them straight up that I wanted someone with integrity. A strong moral compass. Their replies were varied versions of “Good luck with that.” I’ve also mentioned this …