My Sex Life Makes Me Feel Like a Failure

The way intimacy and love both terrify and excite me is taking a toll on my self-esteem.

Melissa Boles
Jul 28, 2020 · 9 min read
Photograph taken by Melissa Boles

I am 32 years old, and I’ve only had sex with one person.

Well, two if you count the guy I met on the Internet who was in an “open relationship” but stopped penetrating me once we discovered I was unexpectedly menstruating. He was worried it would get on the sheets and then his girlfriend would know. The rush I had been anticipating was immediately replaced with one of regret.

With the exception of that unsatisfying incident last year, it’s been … a long time since I’ve had sex. And if I think about it too long, it makes me feel like a complete failure.

Most of the articles I see about women’s sex lives have to do with women not wanting to feel judged for having had a lot of sex. They shouldn’t feel judged. Sex, as I understand it, can be empowering and elevating. Women who have had a lot of sexual partners should never be made to feel less than women who haven’t.

Truthfully, I am jealous of those women.

My lack of sexual partners is not for lack of desire. It might be for lack of trying. It’s certainly directly related to how I assume people will feel about my body and my limited experience.

I have longed for intimacy for as long as I can remember. As an eighth grader, I sat on the side of the pool we used for PE class and listened to a boy ask one of our classmates to be his girlfriend. When she said no, I offered to be his girlfriend. No one had ever held my hand before. It lasted a week before he unceremoniously reminded me that he hadn’t actually wanted to date me and “broke up” with me.

When I was 15, I so desperately wanted a boyfriend that when our English teacher wrote a poem about our class at the end of the year, my defining characteristic was how much I wanted a boyfriend. I don’t know that I ever lived that down.

The most affection I gave and received throughout high school was with my best male friend, a man who wasn’t supposed to date (not that it stopped him) and whose friendship I’m still not sure how I maintained for so long. The small touches and hand clutches were like air to me at the time, and years later people still ask me if we dated. We never did, though I certainly wanted to. His mother would have hated it (as a girl in general and a white girl in particular, I was out of the question for her Muslim, Pakistani son as a girlfriend, though she liked me as his friend), and I certainly wasn’t his type. I knew that even then.

My first kiss came my junior year of high school in a hotel room at the convention center where I was participating in a video production competition. He was a fire cadet from across the state. We kissed twice and then sat stiffly next to each other watching television as my (younger) friend made out with his roommate for what felt like hours before I insisted we go back to our room. I never saw him again.

A year later I kissed a stranger on the city bus on my way to my job as a cashier. He flirted with me at the transfer stop, telling me I was beautiful (which I hadn’t before heard from a man that wasn’t my father), and even though I sat away from him when we first got on the bus, by the time we reached my stop we were sitting thigh to thigh in the back row. He kissed me and ran his teeth over my ear lobe and told me how he’d made a chubby girl beg for her orgasm before and he could do it for me too. When we got off the bus he handed me his phone number and told me I had a great ass as I walked away. I attended a Baptist church at the time and texted my church friend in a panic because I felt like I’d violated some sacred covenant by engaging with him. She encouraged me to throw away his number, so I did, and we made a pact together to stay away from boys.

I felt starved for affection. My childhood was complex, steeped in trauma and self-esteem issues that I felt were hanging around my ankles like a pair of too tight nylons that never seemed to stay where I left them. I would have done anything for someone to show me intimate affection and yet it absolutely terrified me.

At 21, I thought I was in love. Our friendship was intense, peppered with screaming arguments that drove others away from us and a deep shared love for understanding religion. He walked campus barefoot with oversized headphones, wrote notes in the margins of books even if they didn’t belong to him, and left sticky notes for me with songs I should listen to and poems I should read. The summer I went to Kenya he was joyous for me, and when I returned he was the first to wrap me in his arms and demand to hear every last detail. We never dated but oh how I wished we would, desperate to hold his hand and feel the light stubble of his face against my cheek. Our last screaming match ended in physical assault, a broaching of the space between us in a way I never anticipated. It took me 48 hours to report it and years to understand what had actually happened. I spent time with him after, sure I could heal what had broken. The last time we were alone he was a photography subject for me, dancing barefoot with oversized headphones. Now when I see him my entire body tenses.

After college and a series of unrequited crushes, I gave up on trying to be with someone. The idea of online dating scared and frustrated me (it still does) and I resigned myself to focusing on who I wanted to become. I was also certain no one would ever love my fat body, so there wasn’t any point in trying. Then, when I was 27, I stumbled upon someone who seemed as interested in me as I was in him. I felt 15, so uncertain and smitten, fully aware that it wasn’t a forever situation but intent on experiencing it for what it might be.

I felt like a complete loser for not yet having had sex. He wanted it. So did I. He chuckled under his breath when I mentioned never having been with anyone, and when it came up again he told me he thought I was kidding. He was hesitant about being my first, but we weren’t in high school. I was capable of separating sex from love. Mostly.

I’ve never been able to find the right word to describe our relationship. Sometimes I refer to him as my “ex,” despite our never having been in a defined relationship. It’s simpler than “the guy I slept with occasionally for a few months”. I found out years later that he’d been sleeping with several other women at the time. We were never exclusive, but he wasn’t honest about it either. I think that’s what hurt more than anything.

Finally having sex felt anti-climactic in every sense of the word. I had trouble relaxing my mind and then, after the first couple of times, it was obvious that I could have been literally anyone. It became clear to me that there was an emotional component I wanted that I wasn’t getting.

Every six months or so I re-download dating apps I’ve deleted, scrolling through and promising myself I’ll message a certain number of people before I give up. Only twice has it gotten further than online messages. Once I was stood up. The second time I was snuck in through a back door, shushed, and then dismissed when there was a chance his girlfriend could find out.

I love the internet for so many things, don’t get me wrong. I’ve made wonderful friends on the internet and been able to connect with writers and artists I admire. I’ve learned things I never would have stumbled upon otherwise, and discovered new music and films that have changed me. But in the grand scheme of things, online dating makes me feel worthless.

I’ve always wanted the fairy tale. I catch his eye, we engage in conversation, we fall together. Those are the stories I write, and the ones I love to hear. When I meet people, I want to know how they fell in love. Some of those stories have included online dating, but somehow I can’t let myself be okay with that for me. I still have this dream that I’ll fall in love with one of my best friends, which would be so much more likely if less of my male friends were gay.

I am, technically, bisexual, but my sexuality seems to truly be defined as being mostly, and sometimes begrudgingly, attracted to men (largely older than I am), and being occasionally attracted to (and terrified of) middle-aged women. I won’t pretend for you that I’m not aware that part of the reason I’m still single is that I’m deeply hesitant about letting someone in.

As a fat woman, I’m mostly concerned with how someone else is going to see my body. When I look in the mirror, 80–90% of the time I feel good about it. I don’t mind being fat, truly. There are moments, however, when I wonder what someone lying next to me would think, and those are the hard moments. They’re even more difficult when every movie and television show you watch seems to have an underlying diatribe against fat people (but that’s a different story).

Every so often when another article pops up about a woman feeling guilt or shame because she has slept with multiple men, or because she didn’t want to wait until marriage, I wish I could shout from the rooftops. Love yourself, I would say. You let others love and touch you and it went well. You had the opportunity to feel good. Some of us are worried we’ll die before we’re ever touched in that way again.

My sister told me last year that sometimes people are meant to be alone, and maybe that’s true. Most of the time, not having to fit in the needs of someone else is great. It allows me to build the life I want, even if I’m still figuring that out, but at night or after I’ve watched a romantic comedy for the 45th time, it feels a little like hell on earth. The only thing I want more right now than for our country to figure out how to handle COVID-19 is to be held at night.

As a millennial and a woman and someone who went nearly 30 years before being diagnosed with ADHD, feeling like a failure is not new to me. It seems to have been ingrained in our generation, which is both disappointing and helps me feel that I’m not alone. But there’s something about this that feels worse. It seeps into the bones of everything else. Being a woman in our society often means being harassed and assaulted for your body. There are moments in my life when I have horrifically wished someone desired me enough to make me uncomfortable.

Our society has designed a system of desire that both expects women to be chaste and pure and also makes them feel abhorrent if they are not desirable enough. It is a deeply flawed and dangerous path for women to navigate and while there are moments where it feels like it is changing, they seem so few and far between that it’s impossible to see a future where having a fat body and very little sexual experience doesn’t make sexual partners immediately turn away from me. I am scared of a future where I don’t get to experience the love and intimacy we all deserve. I am hopeful for a future where that love and intimacy knocks me to the ground.


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Melissa Boles

Written by

she/her. writer. storyteller. impatient optimist. greater fool. fat queer. @melloftheball.


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