Working On Myself: Men On Dating Breaks

Photography by Nubelson Fernandes on Unsplash.

Words by Brandon Caldwell. Photography by Nubelson Fernandes on Unsplash.

Four men talk about why they needed to take a break from casual sex and dating and what that time afforded them.

“I need to work on myself.”

Six words, nineteen letters. It sounds like a sledgehammer to a relationship. Everything comes to a screeching halt. Instead of a conversation or declaration as to why pulling back for self-reflection and honesty is necessary, it’s weaponized as a means to escape, especially when men hold the phrase in their back pockets.

Last year, Michael B. Jordan endured a painful public breakup. Instead of thrusting himself into another relationship, or taking on life as a Hollywood playboy, he threw himself into his own form of healing: work.

“I’m a firm believer in that what’s for you is what’s for you, and coming out of that situation — not to give it, you know, any energy and kind of move from that — it was an experience for me to grow and learn,” he told CBS This Morning’s Gayle King.

In order to find ourselves better as lovers, we need to find our self-worth. For me, it was coming to understand working on myself outside of sex and relationships meant acknowledging unbroken parts of me, becoming more vocal and refusing to rely on temporary feelings to mask what really was going on. ILY spoke to several men about taking a break from to dating and casual sex, how long they took, and why “working on myself” wasn’t an escape plan, it was a necessity.

There’s no easy way to let go.

“In my 20s, I told women on multiple occasions that I was working on myself when I was ready to move on from the situation. Did I actually work on myself? Yes. I usually just wanted to be alone for a while — “on the bench,” as I called it. Whether that was focusing on work, school or finances (mind you, dating is expensive as fuck and that in itself is a valid reason to be over it.). I was ready to focus on something other than whomever it was I was entertaining. I stuck this pause out for months before I finally decided to step back into the dating scene.

What did I learn? There’s no easy way to let go of someone. You still feel like an asshole if you hit her with the “it isn’t you; it’s me.”

Andrew Lilly

You don’t lose betting on yourself.

“By the time I got to January or February 2022, I kind of got rid of my roster. I was over the Playboy lifestyle and dating at that point was also cumbersome. I felt like the women I was meeting were more interested in the title than they were in the actual relationship. At that point, I was just over going on 4 to 7 dates a week and it wasn’t even for sex cause that was readily available. I had sat through about 2 and 1/2 years of therapy at that point too and worked through a lot of my previous traumas, self-doubts, etc. I also started realizing that what I wanted was sustainable and available, but it wouldn’t appear to me as long as I continued to live the lifestyle I was living. Which wasn’t a bad one, because it was really cool getting to know these women, and their stories, enjoying their company and learning about them.

But the more I was dating and finding out about a lot of these women I noticed their ideals of relationships didn’t match what I was looking for. Add on top of that I was going through my own shit and coming off the pandemic trying to get myself to a level of sustainability for the lifestyle I wanted, so I definitely needed to sit down and come up with that plan.

I was working through depression and anxiety. Realizing I was trying to satisfy the needs of women I wasn’t gelling with who weren’t really reciprocating in any manner that was making my life easier helped me to realize I just needed to sit down. One of my favorite quotes is “You’ll never lose women focusing on money but you’ll lose money focusing on women.” That really just clicked for me one day and I just knew the woman for me would be there eventually

You don’t lose out on women focusing on yourself. It allowed me to become a better person for my now girlfriend. Time to set goals and make plans and how a partner would play into that. A long-term view of things really”

Jason Burton

Six months … and then I was a new man.

“I have always chased ASS. Sex was at the forefront of every single relationship so after choosing to end the relationship with the most beautiful woman I had met yet, I had to go back to the drawing board. After a painful breakup with a woman who taught me what LOVE is, I was right back to where I began. I was right back to the place I was prior to her. Lost! I eventually realized I was depressed because then I was 35+, childless and still out there searching. 

My job at work makes me go to the root of every issue. So I took that approach to getting to know me. Losing her, though not the person for me in reality, made me want to be better. In order to find that I wanted to make sure I was at my best. The process really took about six months and one trip back to my homeland, the Dominican Republic. If I could withstand all the tests down there, I was a new man.

In that break, I learned that I am far more than just good D! I have many different interests and I spent most of my time focused on sex. I was able to speak my mind and share my feelings. I never did that prior. I would openly speak out on matters like male vulnerability and the urban male on how they are brought up misled. I realized I never knew any man that was faithful. NONE! I was always told to get women. My mom is included on that list of folks. I had to let go of “normal” (hood trauma), and re-learn how to behave in a relationship. I gained a new level of confidence that had zero to do with appearance. I picked up new hobbies and finally I was able to forgive myself for allowing myself to hurt so many women in the process. Today, I try to speak with my younger homies and let them know that being with one woman is the dream, especially if she’s the right one.”

Rafael Morales

Stability is key.

“As a semi-successful entrepreneur (by my own standards), I often found myself with an abundance of free time on my hands. How did I decide to fill that free time? Women. Night after night (on a good week) I would spend my time trying to get whatever woman I had a lustful eye on over to my residence. We’d have a night of passion, but the next day we were back to strangers and the process then starts over again. I’m back on the hunt.

You open your IG app, Hinge, Tinder, etc. and you have an unlimited pool of women to choose from not only in your city, but anywhere in the world. The craziest part about it all is they are all within reach now if you have the funds to get to their city or bring them to yours. There lied my problem. 2 DM’s in, I was already booking myself a flight and hotel and jetting off to meet these strange women in these strange cities. I was basically on a tour of the U.S., even had a few stints where I would fly from my city to one woman’s city, then from her city to the next woman’s city. It adds up!

While I was building up my budding roster, I was at the same time neglecting my day-to-day duties in my business. What once was a smooth and streamlined process has slowly begin to unravel in to a chaotic mess. I was putting the thrill of chasing women over what provided the free time for me to chase the women, if that makes sense. In doing so my business essentially fell to the wayside and I was on the verge of having to do what I feared the most; reverting back to a W2 worker (no knock to my 9-5ers).

After some self-reflection, I knew I had to limit my access to women. Give up all this pussy cat in my lap, no looking back? Yes. I struggled, and I do mean struggled to stay off all forms of social media, dating apps, etc. until I was financially whole again and my business goals were met. I filled my time with reading articles on Reddit, reading self-improvement novels, journaling, trying to improve my fitness levels (emphasis on trying).

In doing so I was able to not only get my business back to where I needed to be but take it to where it’s never been before. As well as I was able to discover new hobbies which I had long been yearning to do. I was able to focus on things I solely liked versus what I thought women would like me for, and I realized that brought me as much satisfaction as chasing women.

Fast forward to today, I’ve since started a new venture and added another notch under my entrepreneurial belt. I am back on the prowl for new women to mingle with, but it’s much more controlled now. As a great philosopher once said “I love the game, I love the hustle!” — Lorenzo Tilley

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