Now Reading
Dating in Your 20’s Isn’t for The Weak: Here’s What I’ve Learned

Dating in Your 20’s Isn’t for The Weak: Here’s What I’ve Learned

I spent most of my twenties wanting to be a hoe.

Yes, you read that right. I suppose I should explain. I don’t mean hoe in the sense of sleeping with every man I meet, although if that’s your thing, do you sis; I’m all about the girls doing whatever they want. What I really mean is a woman who knows what she wants, puts her feelings first, and will drop a man that isn’t treating her how she wants to be treated, a woman who doesn’t care what anyone thinks, and of course goes out on all the dates, because why not. Essentially, I wanted to be the reason city girls were up by a million—  the girl who isn’t a hoe according to urban dictionary, but who is a hoe according to men because she acted like them. 

My first “adult” relationship ended faster than it began. I was 19 and though my high school sweetheart and I had parted ways for some time, I still didn’t want to entertain the thought of someone else. However, spring semester freshman year came around, which meant two things, one, I had survived my first brutal winter in Syracuse and two, I needed to be outside. To celebrate the change in weather, I went to a party. The drinks were flowing and music bumping like in the movies we all watched before college had even started. A boy asked me to dance and I couldn’t resist. As I made my way out he asked for my number. We laughed because the 3-4-7 made him turn to me and say “oh, you from Brooklyn.” I guess there was some excitement because my area code meant I was close to home and not from some far away place which meant we were likely to never see each other again. I could go into more detail of my first real heartbreak but to make the extremely long story of my extremely short relationship, short, we did see each other again and after many ups and downs, he decided to end our relationship. After that, I took a two-year break from dating, I guess you could say I was in mourning. 

After the mourning period was over, I slowly made my way back outside by “dating” my supervisor at my first job. My friends say I was dating him but I beg to differ. I will say the lesson I learned from this one was to trust my gut. With him it was the typical don’t worry about that girl but worry about that girl situation. I saw this ex’s name pop up in his phone and my gut told me they weren’t over. Less than three months into whatever we were doing, he ended things with me and got engaged to the same ex I was worried about. 

Gut- 1, Ashley- 0

The next man that is significant enough for me to mention was a guy from college. Yes, college was over and I definitely should have let our potential romance stop at the day dreams I’d have of what our post-college lives would be— both of us hella fly and madly in love, like A$AP and Rih in the recently released D.M.B video. If you’re wondering why I chose to live in the past, he was the guy that never happened and I was just as curious as he was. He was also the guy everyone warned me about, the guy who in my mind was different with me, because I’m me and if anyone can turn him into prince charming, it’s me because I am THAT girl. Turns out I wasn’t that girl, but just a girl, with no powers to make him someone he did not want to be. Funny enough when I think about him now all I hear is Maya Angelou’s when people show you who they are, believe them and of course, my Jamaican mother’s who cyaan hear mus’ feel. Quick translation on that for my non-patois speakers: Those who can’t hear/don’t listen, must feel (the consequences of their actions).

For years I carried my first “adult” breakup with me. I was the villain in that story and that was heartbreaking. I then overcompensated and put the men who didn’t deserve to be on pedestals on the highest imaginable. I didn’t listen to myself, I didn’t make the decision to put myself first. I was scared to lose men who weren’t even mine and at the time, choosing myself was the harder decision. You see, there has always been this inner battle between who I am, who I want to be, and who people, men in particular, want me to be — who men wanted me to be was always the reigning champ. 

From 25ish on, the years do really start to blur after a while, I don’t think I took anyone seriously. Well, I didn’t want to take them seriously because they had already made their intentions clear. They were there for fun and that meant I had to get on board if I were to survive in the current dating landscape. I got into things with someone I went to middle school with and someone I worked with yet again. I also got on the apps, matching white men who fetishized me, men who ghosted me and popped up when it was convenient for them, and men who ultimately were unsure of what they wanted. 

See Also

I spent my twenties wanting to be a “hoe” but not because it was the life I knew I deserved to live. I wanted it because overcompensating got me nowhere, and in my mind the exact opposite had to make me feel better. I could never find this happy medium so I had to match the energy of the men I occupied my time with. It truly seemed like I had to beat them at their own game even if it meant destroying myself in the process. As I near 30, I think that this had to have been the biggest disservice I’d ever done to myself, going back and forth between two extremes that didn’t really serve me. 

I can think of many lessons when I reflect on my very chaotic dating journey. I won’t pretend that I’ve learned a million things about men because I haven’t and truthfully this isn’t about them. I learned that I yearn to live a life that is carefree and full of confidence and peace. I think as people, we spend way too much time trying to get others to like us. We want to be agreeable because there is a myth that if we disagree we are bound for a life of solitude. Though, to be fair, choosing to be single is not the treacherous, lonely path it’s been made out to be. Black women especially, are now finding community and family in loved ones, friends, colleagues, and much more.

In life, we are faced with many choices and we make the ones that we think are best at that moment. The problem is it is not always the choice that is best for us in the long run. If you are a twenty something, now entering the dating game I urge you to listen to yourself. If it does not feel right, don’t do it. Do not hurt yourself to make someone else happy. Do not feel the need to stay because you think there is no one else out there. Lucky for us, the beauty in dating and in life is that there is never just one opportunity.  

Scroll To Top