What I’d Tell 20 Year Old Jess About Sex




Oh 2011. You seem like such a distant memory. I was 20 years old and had just come off of taking a semester off from college to work full-time as a nurse’s aid at a major hospital in Upstate New York. I realized that no, I didn’t actually want to become a doctor or a nurse. I wasn’t sure what I wanted to be, but I figured I better go back and finish my bachelor’s degree in biology or risk being poor and miserable for the rest of my life. (eye ROLL these were my actual thoughts) 

I felt like I was in a pretty good place. I had bounced back from gaining 40 lbs during my senior year in high school/freshman year of college and was in the best shape of my life. I got good grades. I had lots of friends. I had recently broken up with my boyfriend of 7 years, which was the hardest thing I’d ever had to do at the time. We loved each other but didn’t bring out the best in each other, and it became more and more obvious as we became young adults. Although the decision was difficult, and the grief was real, I came out of it feeling confident and excited to move forward. 

Up until that point, I had only had sex with my high school boyfriend. We thought we were going to spend the rest of our lives together, and I don’t regret that decision. But I do realize that it was the beginning of a trend that played itself out more in my early twenties. I wanted affection and intimacy, and I thought sex was the way to get it. With my first boyfriend, I thought that having sex with him was the way to gain his love. I was young and we did in fact fall in love. I was so lucky to have that relationship with him. But it could so easily have gone the other way. I like to think I have a good intuition about people, and I had an intuition about him. But verbally we had never communicated what we wanted out of our relationship prior to engaging in sex. This foreshadowed what would be a theme in my life later on.

So here I am, single and ready to meet people, and what do I do? I thought that I was confident at the time but in hindsight I didn’t see even a fraction of my worth. In two instances over the next two years I would begin sexual relationships with emotionally unavailable men, only they weren’t just sexual relationships to me. Let me be clear: these weren’t bad guys. I’m telling you the mistakes I made and how I sabotaged myself so that you can gain clarity from your own experiences. Or incase I can go back in a time machine and tell myself this stuff someday. Kidding.

So when you’re not really secure in who you are/what you offer/what is available to you,  you tend to jump at opportunities when they present themselves to you. I thought the feeling that I had when I fell head over heals for my first boyfriend couldn’t happen again. I thought it was a product of the naivety of childhood. (I’d later find out this wasn’t the case). I think this also plays into the scarcity mindset that a lot of us suffer from: thinking there isn’t enough happiness, resources, love, people, etc. to go around so you have to be possessive of these things. So, assuming that I’d be living a life of mediocre emotions, I clung to the first man that made me feel special. He was sweet as hell but just not ready to be in a relationship whatsoever. He told me that. I thought I could change his mind. NOOOOOOO. Lesson number one: you should never have to convince someone to love you or be committed to you. Therein lies heartache. I thought, “surely if he spends time with me and we become physically intimate… that will change.” Nope. 

I spent the better part of a year trying to draw blood from stone, and my confidence suffered tremendously. But I hadn’t quite learned my lesson yet, so I decided to fall for my friend that already had a girlfriend… because apparently he was the only available guy on the planet? Don’t ask me what I was thinking… I can only attribute it to incredibly low self worth. That was a fairly miserable several months as well. I wanted to be loved, and I thought having sex with someone was the way to get there. That situation crashed and burned as it should have due to the idiocy of all parties involved. Oh but I wasn’t done yet.

A few years down the road and I’m in Hawaii, happy but also jaded AF in the relationship department. I actually had myself convinced I didn’t need a partner and needed to have a more casual approach to sex. I started using tinder and going on dates with guys and did have a blast doing it. Just drinks and food and conversation, never sex. Until I did have sex with one guy and caught feelings hard. If I’m being honest, I wouldn’t have had sex with him in the first place if I didn’t. I know that about myself now. But I needed the universe, the cascade of my own actions, to show me again how I was fucking up.

What I wanted was an emotional connection to another person. A bond and alignment with someone so strong that we could do life together. I didn’t need another person for sex…I could do that on my own if I just needed to get my rocks off. What I desired was a companion. 

I have been privileged to have two loving and committed relationships since my episodes of looking for love in all the wrong places. I fell in love on Oahu to a man that loved me more than I thought anyone ever would. He renewed my hope that the magic of love still existed. When he died suddenly, I struggled tremendously, but having seen the amount of love he had for life and for others, I knew that love was abundant and that I would find it again. 

I now find myself in this loving marriage to Adam that I take so much pride in having manifested for myself. A relationship that from the start was based on shared vision for our lives, humanity, the earth, and open communication. I feel so much gratitude, but I also feel obligated to share with the world that although sex is one of the most beautiful joys of life, you must realize when you are using it as a substitute for something else. You must not mistake sex for true intimacy. You must not think that sex creates love or commitment. It does not. Being reciprocally open and honest and vulnerable to another person does. You can not make someone care. You can not make someone love you. And you don’t have to. Love is abundant. Accept nothing less than what you desire.