(Gabor Balazs via Shutterstock/Salon)

How anal sex ruined my relationship

The evening was so perfect I thought he might propose. But he had a very different proposition in mind

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Marilyn Friedman
July 13, 2015 4:00AM (UTC)

It’s New Year’s Eve, and I’m at the W Hotel in Manhattan with a boyfriend I’ll call Liam. We’ve been together for over a year, and this is the moment I’ve been waiting for my whole life: He’s going to propose.

The night so far has been perfect. We’ve just come back from a party. The champagne arrives from room service in a silver bucket. Liam hands me a glass. His piercing green eyes and jet-black hair are striking against his white tux. He motions for me to sit next to him on the bed. “I want to ask you something,” he says. My heart is pounding as I stare at the twinkling Manhattan skyline.


I stick my hand under the pillow, because I always imagined that when a man proposed, he’d hide the velvet box there, like an adult version of the tooth fairy. But there’s nothing under the pillow. It’s probably in his pocket. I sip my champagne and try to calm down.

That’s when Liam whispers, “Tonight, I want to do it up the butt.”

Most women would think, He’s not going to marry you, dummy. But in my twisted 26-year-old brain, I still think that marriage isn’t completely off the table if I give in.

Other women might think, That’s hot that he wants anal. Go for it!

But I’m really uptight. My old-fashioned Russian mother drilled things into my head like, “If you give the milk away for free, he won’t buy the cow.” I believed her.

I was a virgin until I was 20, when I finally had sex with my college boyfriend. I cried the entire time and asked him if he was going to marry me because I couldn’t live with myself if he didn’t. After he promised he would, I made him cuddle me for hours. This went on for a year until he cheated on me with a waitress at Steak and Shake.

After that, I had six failed relationships. This was my pattern: I’d meet a guy I liked. We’d look deeply into each other’s eyes at a fancy restaurant where they comb your tablecloth. He’d want to have sex, and I wanted to do it too, now that I’d been defiled.

But after we’d have sex, I’d feel like a slut and become that needy girl every man is afraid of. I’d call too often. I’d need too much reassurance. He’d start spending lots of time with his friends at Paddy O’s, the perfect place to complain about your crazy girlfriend over a pint of Guinness. And before long, he’d stop calling and break up with me.


With Liam, I was determined to do things differently. When I first spied him at a swing dance at the Supper Club in Manhattan, he was leaning against the mahogany bar drinking a martini in a neatly pressed button-down shirt. He asked me to dance a lot that night and we exchanged numbers. I invited him to my birthday party the following weekend in Boston, not expecting him to show. But he rode his motorcycle three hours in the pouring rain to come to my party. He gave me a limited-edition swing music CD box set and gray pearl earrings.

Liam stayed with me that weekend. We had amazing sex and talked for hours over cannolis at an Italian restaurant in the North End. Liam was 29, and he was already an executive at a top engineering firm. I’d found my prince.

He said, “I really like you,” and kissed me deeply. Then he wrapped my arms around his waist as I sat behind him on his motorcycle. We drove through Harvard Square, blasting through piles of red and orange leaves. I was in love.

Liam left to go back home. I worried, What if he doesn’t call? What if there is an Irish pub nearby? 


I decided I didn’t want to ruin it with Liam. So I called up a professional: my sister Rochelle. We both had big butts. But Rochelle was more disciplined than me. By starving herself and exercising two hours a day, she turned herself into a skinny, blond goddess. She married a handsome surgeon who lived in a mansion on the North Shore of Chicago. She was the ultimate playboy tamer.

Rochelle said, “If you want to get that ring on your finger, it’s going to be very painful and you have to be fully committed to the program that I put you on.”

“Just tell me what to do,” I said.

I got a $300 wardrobe at Anthropologie and a fancy bob at a Newbury Street salon instead of my usual bowl cut at Fantastic Sams. I looked in the mirror. I no longer saw a gawky Jewish girl, I saw Diana, the dating huntress.

Next, Rochelle taught me the phone was my enemy. I wasn’t allowed to call Liam. We practiced. The phone rang. When I picked up, it was Rochelle, calling me on my housemate’s line. She chastised me. “What did I say? Don’t ever pick up the phone. Let it go to voice mail so he thinks you’re out. And when you call him back, respond to everything he says with, That’s awesome!”


Rochelle forced me to exercise. “Whenever you have the urge to call him, don’t gorge on gummy bears, do sit-ups,” she said. “You’ll have a six-pack and he’ll be dying to talk to you.”

I followed her program religiously. When Liam didn’t call for more than a week, I didn’t cave. I did crunches. I sat shivering on my futon in my drafty Victorian apartment, staring at my cordless phone, willing it to ring. Waves of insecurity pummeled me. Maybe he’d lost interest and found someone else. I called Rochelle for support. “Be strong,” she warned.

Eventually Liam called. I pretended to be unfazed.

When we were together, Liam acted like I was the most important person in his life. He monopolized me at swing dances. He took me on romantic picnics. We had great sex, and I didn’t turn into crazy Marilyn. I fooled him into thinking I was the calm, laid-back girl of his dreams. That’s when he asked me to spend New Year’s with him.

But now, at the W hotel, I don’t know what to do. Rochelle didn’t cover butt sex in the training. I try to call her from the bathroom, but she doesn’t pick up.


I panic. “OK. Go ahead,” I say to Liam.

He smiles and unzips my dress. He pulls back my pink lace thong and after some shoving and a lot of lube, he puts it in. It feels like my butt is being jackhammered by a giant apple corer. When it’s over, he asks me if I liked it.

“That was awesome,” I lie. I think, Now that I’ve done this, I’ll get my ring.

Liam excuses himself to go to the bathroom. I hear water running. He yells, “Oh god!”

“Is everything OK?” I ask. Silence.


“Sure, if you’re cool cleaning poop off your dick,” he says when he comes out of the bathroom.

I don’t even have to get crazy this time. He just stops calling. It’s over.

I have a dark few weeks. I put on my sweat pants. I hit the gummy bears hard. I cry a lot. I’d degraded myself to hang onto a man, and it didn’t even work.

But something inside of me clicks. I decide: I’m done with guys like Liam. I’m finished pretending to be someone I’m not.

A relationship that doesn’t allow me to be a human being with needs and preferences isn’t worth having, no matter how good it looks on the outside. Maybe I was cheating myself by not believing I deserved a man who could give me the support and attention I craved.


So I pack up my car and drive across the country. I swing dance in every city along the way. I have fun. I focus on fulfilling my own needs.

When I finally make it to San Francisco, it’s 10 o’clock at night. I go to Club Cocodrie in North Beach, where I know they’ll have swing dancing. Across the room, I see a tall, broad-shouldered guy with Buddy Holly glasses on. His name is Jeff. Jeff asks me to dance, and then he asks me out. After our first date, he calls me every day because he actually likes me.

Jeff never abandons me, not even when we’re trapped in a tiny hotel room in Madrid and I have such bad food poisoning that it gives me the runs and I can’t stop throwing up.

Before Jeff, I was convinced that dating was as stressful as piecing together a complex puzzle. But once I met the right guy, it was easy and clear. Jeff wanted to be with me, and I wanted to be with him. He was my best friend, and he accepted the real me.

In the end, I got my ring under the pillow. And I didn’t have to take it up the butt to get it.

Marilyn Friedman

Marilyn Friedman is a freelance writer who has been published in the San Francisco Chronicle, Narratively, and The Frisky. She co-founded Writing Pad, a creative writing school in Los Angeles, San Francisco and Online.

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