Five things I learned from sleeping around in my 20s

For the span of about five years in my mid-twenties, I was a whore. Not the kind of whore who accepted payment — although I don’t judge those who do— but the kind who had a lot of casual sex and numerous one night stands. The kind who lost count of how many partners she had. The kind who would be hard-pressed to recognize some of the men I spent time with if I ran into them on the street.

Believe it or not, I look back fondly on this time in my life. Not because of the sex, but because of what I learned about myself during this time. The more I think about it, the more I realize that my mid-twenties, in all of their promiscuous glory, helped to cement my character. This period in my life made me more open-minded and more adventurous; empowered me to ask for what I wanted and set boundaries; made me more self-confident; forced me to become stronger and more resilient; and taught me important lessons about personal responsibility.

1. Keep an open mind, try not to judge too harshly, and try new things

My approach to sexuality and sensuality was shaped during this five-year period. My sexual philosophy boils down to this: as long as it’s legal and between consenting adults, I don’t care what you do behind closed doors. I may not personally enjoy it. I may not understand why someone would be turned on by it. But, it’s none of my damn business. This approach stems directly from sleeping with a smorgasbord of men. It was inevitable that I would encounter a variety of fantasies and kinks, but for someone who had had a relatively vanilla existence until then, it was eye-opening.

I learned that no matter how unassuming someone looked on the outside, they often had a fantasy or a kink that they wanted to explore. There was the guy who liked a finger up his butt; he also wanted me to accompany him to a swinger’s club. There was the guy who liked men…and women…and occasionally dressing in women’s clothing. There was the guy who liked asphyxiation — both giving and receiving. There was the guy who liked ropes, and bondage, and paddles, and spanking.

The thing is, these were all perfectly nice, intelligent, gainfully-employed, generally respectful guys. It dawned on me that maybe I shouldn’t be quick to judge people about what turned them on. It taught me to be more open and accepting of people as well as to be much less judgmental, not only in the bedroom but in everyday life.

If I had only slept with people with whom I had a long-term, committed relationship, I would have had a much narrower experience of what makes people tick in and out of the bedroom. I also would have had a lot less fun.

2. It’s okay to ask for what you want and to say no to what you don’t want

I found it liberating to know that there would be no long-term entanglements with the majority of men I slept with. This was a time of experimentation and freedom for me. Although it was odd at first, I became comfortable with talking openly about sex with my partners. I learned to ask for what I wanted, whether that was just a back rub or something more x-rated. I also learned, through trial and error, what my boundaries were and how to confidently decline activities in which I didn’t want to participate. I learned how to communicate really well, ironically because of the lack of emotional entanglement. People were less likely to get their feelings hurt because there was much less emotional baggage in a casual relationship.

Sex is supposed to be enjoyable. It’s not enjoyable if both people aren’t into it, therefore both people should be comfortable and confident expressing their desires as well as their boundaries. Be confident with expressing your needs and your desires, but also know your non-negotiables and stick to them.

Asking for what you want and saying no to what you don’t want is something we each have to navigate on a daily basis, at work, with our friends, in our families. There will always be some things that we don’t want to do something but me must; and there will always be times when no matter how much we want something, we won’t receive it. However, I would argue that in general, it’s always better to ask than not to know the answer, and to protect your boundaries on those things that are most important to you.

3. Work with what the good Lord gave you and be confident

I am not unattractive, but I am not model material. I am too short and too round and too plain. I wear glasses. But, yet, I’ve had very little trouble finding sexual finding partners when I wanted them.

I had always been a little self-conscious growing up. When most of your friends are thin and blonde and you are not and when those thin and blonde friends are getting all of the attention and you are not, it can do a number on you. But, luckily, starting in college I began to discover that it wasn’t my weight that was holding me back; it was how I thought about my weight that was. Being fat wasn’t a sentence of life-long celibacy, it just meant that I had to work a little bit harder to find guys who found me attractive. I didn’t have the luxury of having a body that fit the beauty standard, so I learned to play to my strengths, which included both physical assets and personality.

This was a radical idea to me: embrace who I was and work with what I had. I already knew I was funny and smart. When I became comfortable in my body, that’s when everything fell into place. I found myself with plenty of partners. Some of them were men who weren’t usually attracted to fat women and said things like “you’re so comfortable to snuggle with.” Well, yes, when you’re built like a love seat, it does make you pretty comfortable to lean against. I learned that there isn’t a type who’s into big girls; they ran the gamut from tall to short, big to thin, and all races and backgrounds.

I am not naive enough to think that all of the men who hooked up with me loved my body. I am very aware that for some of them, I was nothing more than a warm place to park their dick for the night. However, I also was not so naive to think that this same thing didn’t happen to beautiful thin women as well. It is just part of the game and once I accepted that, I enjoyed myself that much more.

4. The only way you build resilience is by being uncomfortable; also, rejection won’t kill you

As I entered my 20s, I was admittedly pretty clueless about men. I hadn’t dated much in high school or my first two years of college. I did have a long-term relationship at the tail end of college, but it was long-distance and so it wasn’t the most traditional relationship. So, when I went on my first date post-college, I actually was naive enough to take the guy at face value. I thought that if he said he’d call the next day, he’d actually call. After all, we both were adults and I thought we had hit it off. I was mistaken, of course.

Admittedly, I remember being a little disappointed. Not terribly, but I wondered what I had done wrong. What I could have done better. So, the next date I went on, I tried even harder. More or less the same thing happened. I started to beat myself up and get a little down in the dumps about it. But, I tried again and met a guy that I hit it off with. We even had a couple of nice dates and a couple of nice phone calls. However, it was also very short-lived.

I decided shortly after this that if dating wasn’t working out, at least I could have sex.

Needless to say, just because I started sleeping with men instead of trying to date them, that didn’t mean that I wasn’t being rejected. I was still turned down, or not called again, or even, once or twice, completely ignored when I found myself in the same subway car with a previous partner. However, there were men that I genuinely hit it off with and with whom I had a casual, sex-based, but still real, relationship.

I am fully aware of the irony of expecting some sort of common courtesy from some guy I fucked the first night I met him. But, as I said, I still was a little naive.

I won’t lie, rejection was hard. It really hurt. It made me feel stupid, and ugly, and unwanted. I cried (and bitched and moaned). Then I took some time to examine the issue logically. I decided I had two choices: keep sleeping around and get rejected or stop sleeping around, try to find a boyfriend, and probably still end up rejected. I was 24. Sex won out. So I became comfortable with and accustomed to rejection and it was like a weight was lifted off my shoulders.

It was by learning to accept that rejection was part of life that I learned to be resilient. I learned that it wasn’t the end of the world if someone didn’t want me or if I wasn’t their type. I learned it wasn’t the worst thing in the world if someone didn’t call me the morning after. I learned I would not die of shame and embarrassment if I hit on some guy and he turned me down.

I can thank my resilience for introducing me to my now-husband. The night we were introduced by a mutual friend we clearly had sparks, only a couple of hours after meeting. I was curious to see where it all would lead, but I wasn’t caught up in worries about rejection and what ifs; I wasn’t worried about making sure that I acted just right so he’d want to see me again that week. I just relaxed and let the evening unfold naturally. He and I have not been apart since that night.

5. Taking personal responsibility for your actions is part of being a non-sociopathic adult.

When you spend your twenties sleeping around a city, you either learn to be responsible for your decisions or you learn to blame everyone else for your problems. I could blame the men who didn’t want to date me for putting me in the position where I relied on casual sex instead of long-term relationships. Or, I could be honest with myself and accept the fact that I just liked sex. I could blame the guys for not calling the next morning, or I could be a big girl and admit that you can’t really expect that much out of someone you just wanted to fuck. I could blame my weight for me being single or I could accept the fact that I liked french fries too much and my weight wasn’t decreasing any time soon.

Once, very early in my adventures, I got chlamydia. I am not proud of this and I can already hear people tsk-tsking, but sometimes it happens. I am lucky that chlamydia is both common and easily cured. The doctor asked me how many partners I had had. I responded, “in what time period?” and was greeted with an uncomfortable moment of silence. She told me that I had to contact everyone from the last 6 months, give or take, so they could be tested.

This whole situation, from the doctor’s call to having to tell my previous partners, was super embarrassing, but part of being an adult is sucking it up and doing the right thing. I sent several awkward emails to men I had been with during the previous months. One guy who received my email thanked me very kindly for letting him know and informed me that he was negative. One guy gave me a death stare when I ran into him by accident a few weeks later. I was seeing someone regularly at that time, so I felt that I had to tell him in person. He was relieved that I wasn’t pregnant and we went out for dinner.

I could have very easily avoided embarrassment by not telling any of the guys I had been with. I could have very easily avoided embarrassment by not telling any of you guys about it. However, I believe in holding yourself accountable for your actions. Don’t try to shift the blame. Don’t try to become defensive. Acknowledge the mistake, apologize for the mistake, try not to make the same mistake again, and move on. This is what being a grown-up looks like.

As I said at the beginning of this story, I have no regrets from this stage in my life. It was just a stage and I learned a lot — a lot about myself, a lot about people, a lot about life. It wasn’t an easy time, but it was a time of fun and freedom, growth and experimentation, and I’m happy I was able to experience it.