What I've Learned After Two Years of Casual Dating

Shadows of a girl and boy making a heart with their fingers

When I was 20, I decided to give casual dating a shot. I felt like I was falling behind, everyone around me seemed to have someone. However, the main reason was I’ve always been naturally reserved and awkward when meeting new people, even more so back then. I worried that if I didn’t start getting some experience soon, I’d end up having painfully awkward dates in my mid-20s because I never learned how to navigate them. Here are the top 5 things I learned!

Your first “breakup” does indeed hurt the worst.

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The worst “breakup” I had (I was never anyone's official girlfriend, I went on dates with 10 different people, ranging from a single date to talking for nine months) was with the very first guy I met. I had deeper connections with other guys (and worse experiences) but somehow, his absence left me devastated. I lost 10 pounds! I think it hit me so hard because he was the first guy I actually liked in a long time. I got so used to him being around, and then one day, he was just gone. I felt everything all at once and I didn’t know what to do with myself. But with time, I was fine. Eventually, I stopped stalking his social media (for real). Suddenly, one day I realized I no longer thought of him. The next time it didn’t work out with a guy, I knew that with time I would be fine. 

I like to move slowwww and most guys don’t...

It takes time for me to get comfortable with someone. I truly want to get to know someone. Through dating, I realized I wished I could build a real friendship first before jumping into a relationship, and I never quite got to that point. It felt like guys, or at least most of the ones I dated, weren’t interested in getting to know me as a person. The guy I talked to the longest, one night on a late call, I asked if he considered me his friend. He immediately said, “No, you’re my girl, not my friend.” I thought maybe I’d offended him by accidentally friendzoning him, so I clarified, “Yeah, okay, but like… in addition to that, do you see me as your friend?” And he just said, “No. You will never be my friend.” After, it became more evident that the guys I dated saw me as a role to fill. The only real qualification? Being a girl they found attractive. It was hard to pick up on at first because they all seemed like nice guys. They’d take me out, pay for everything, text and call me consistently, all the things that, on the surface, make someone seem genuinely interested. But I eventually figured out how to tell who actually cared about me. It wouldn’t take long before they’d ask me to come over (conveniently late at night). The first time I said no, they’d let it slide, almost like I had a “pass.” But by the second time? That’s when their vibe would shift (again this wasn’t all of them but enough of them to observe this trend). Ultimately, the biggest thing I learned is that I want to be friends with whoever ends up being my boyfriend. I like to move slowly and take my time to get to know all the little things someone else might overlook. That’s my qualification. Once I realized that it became so much easier to walk away from guys who didn’t meet the mark.

Don’t do anything that makes you feel uncomfortable.

I know, duh, but let me break it down, both in terms of intimacy and non-intimacy.

Intimacy: This is a tricky topic because everyone has different levels of comfort with it, and that’s totally okay! When I first started dating, I would worry about how far a guy wanted to go. Since dating was new to me, I wasn’t sure how far I even wanted to go or how to address the topic. My only advice? Ask yourself, are you going to feel bad, sad, or uneasy about something later? If the answer is yes, don’t do it. The right person will always want you to feel comfortable above anything else.

Non-intimate moments: In the early stages of dating, don’t waste your energy going on dates you really don’t want to go on. I put up with a few just because I wanted the guy to like me. And I don’t mean, like, mini-golfing when I wasn’t in the mood. I mean stuff like a last-minute invite to see some random band I’d never heard of, after pregaming with a bunch of guys I didn’t know, plus dropping $40 on a ticket to some sketchy venue. (For the record, I did not go to that) But every time I said yes to things I didn’t actually want to do, it felt like I was giving up little pieces of myself just to keep a guy interested. And when things ended, the “breakup” hit harder because I wasn’t just losing them, I was losing parts of me that I had sacrificed trying to fit into their world. 

Say that shit with your chest.

I’m going to break this into two parts: declaring your feelings and when a guy pisses you off.

“I have a crush on you” neon sign.

Declaring your feelings: The early stages of dating are fun, but eventually, I start wondering where this is going. I get anxious and used to fear coming off as too intense. I’d give it a week, maybe a month, waiting for some kind of signal to ease my spiraling. But I’ve learned it’s not worth living in that emotional stage. Now, I’m straight up. If I like someone, I let them know. I trust the right person will value my honesty and straightforwardness, it's simply part of the way I love. If I don’t want to continue, I let them know that too. 

When a guy pisses you off: Keeping everything to myself helps absolutely no one but the guy who pissed me off. I no longer minimize my emotions to make a guy feel comfortable enough to stick around a bit  longer. I’ve gotten much better at voicing when something bothers me, but when guys keep crossing those lines, that’s where I still struggle. Now that I’m more upfront if I feel like someone is purposely trying to hurt me, I get super defensive and it’s hard for me to trust them again so I just walk away. It’s not fully about me being mad. I just lost interest. In my mind, I’ve already expressed how I feel, and if nothing changes, then the real decision is whether I want to keep putting up with that person or not. Regardless, I will share my feelings whenever I want to. I like to talk about feelings (unlike several of the guys I dated). The difference between bottling everything up and actually speaking my mind is huge. When I kept things to myself, it took me forever to move on. I’d replay every moment, wondering why I didn’t say anything. Those feelings would linger for days, weeks, even months! I’d even catch myself talking out loud about it, literally having full-on conversations with myself. I felt insane. When I spoke my mind, though, it was different, once I said everything I needed to say, there was nothing left for me to hold onto, and they stopped taking up space in my head.

Those shirts you kept from him? Use them for the gym.

I had a few shirts, and for the longest time, I didn’t know what to do with them. I had grown attached, I liked the way they fit, and I even wore them to sleep. Every time I saw them, they reminded me that I wasn’t over him yet, and that frustration only made me angrier, especially when I’d accidentally spot them while picking out an outfit. I even shoved them under my bed. Now, instead of seeing them, I was just thinking about them, knowing they were still there. I brainstormed what to do with them, return them? Burn them? Donate them? Nothing felt right. One day, I was feeling too lazy to go to the gym. I was trying to figure out what could motivate me and I thought of the shirts. Would it be crazy to take those shirts to the gym, just to make myself angry enough to power through my workout? Who cares, right? So, I did it. And for three months, those shirts became my pre-workout. Eventually, the frustration faded. They weren’t the shirts I slept in anymore, they were gym shirts, soaked in sweat, repurposed and refined.

I think everyone should go through a casual dating phase. It taught me so much about myself and what I actually want in a partner. I’ll admit, though, at some point, I was dating just to learn more about myself, like I was playing Love Island in real life. So now, I’m taking a one-year break from dating. I have to sit with all of these experiences for a minute. I know I’ll keep learning about myself, just in a different way. And honestly, not all of my experiences were negative. In some ways, I’m grateful for the people I met along the way. When I look back at some of the things I put myself through three years ago, I can’t help but think how cute I was trying to figure it out. I’m still naive to love but I’m looking forward to giving dating another try soon.