How I Overcame My Insecurities In Dating

Evan Magor
5 min readMar 4, 2015

Ever since I was a kid people always thought that I was “serious.” The truth is that I was miserable. I wasn’t smiling because I wasn’t happy. I felt alone and misunderstood. I thought that if I could just find a girlfriend, all my problems would go away. I was nerdy, short, and unpopular. Like many, I was destined for rejection and lots of it. I won’t lie, I wasn’t at the bottom of the food chain. I was fortunate enough to have a few qualities that helped me acquire some decent experiences when the circumstances were right. I even had a few short term “girlfriends,” whatever that meant back then. But, I unfortunately ran into the same problem again and again. I was completely and utterly insecure, and it did not take long for any girl to notice my resulting behavior before they “ran for the hills” as we say.

Finally, my 3rd year of college came around, and I encountered my turning-point. At the time, I had a summer job canvassing on the street for donations, as I actually had some great people skills. Talking to people was never a problem. One day, a gorgeous blonde girl turned the corner and I felt butterflies emerge in my stomach like bats out of hell, because I knew I had to try something. She stopped for me, and I rushed through my speech just so I could skip to asking her out already. I quickly blurted, “So, can I call you some time?” She quickly jumped, “Yeah! I get off work at 6!” I was screaming internally, “Holy hell! Yes, yes ,yes!” while quietly muttering back, “Yeah, that sounds good.” We had a couple of nice dates, and as we were saying goodnight on the second date, I had a defining moment. My insecurities were bubbling. Before our date even, I felt sick to my stomach and couldn’t eat anything, wondering if she truly liked me. I asked myself, “How do I know if she’ll ever talk to me again after this?” So, then I proceeded to ask her. That’s right. At the end of a date, I said this: “So, when can I see you again?” Her eyes dropped down and we both knew that I just sounded like a complete wuss. I was a complete noob. Even after her response, I proceeded to nag her for a more defined answer. It just so happened that she never spoke to me again after that date. I know that you might be thinking that there’s nothing wrong with the way I acted. Let’s shelf that argument for another day, because I’ve got plenty to say on the subject. The point is, that I went home and I knew it was time for a change within myself. I was going to conquer that feeling, and I was finally going to be able to keep a girl long enough to actually call her my girlfriend.

Here’s how I finally conquered my insecurity: I continued to ask girls out and face more and more rejection. When I texted a girl to hang out and she didn’t respond for 10 minutes, I could feel the horrible feeling churning my stomach. One day, I finally had my eureka moment. I was waiting for a text from a girl while I was at the gym, and I finally realized, that right before that negative feeling started coming over me, there was a little voice in my head saying something. And that little voice was actually saying out loud, although it had always been too quick to notice, that I simply wasn’t good. That I wasn’t cool. That’s how my brain had been explaining these events. She’s not texting me because I’m not cool. This little voice had been the cause of all these horrible feelings my entire life, and has been crippling my confidence. Now, how did I get rid of that voice? I simply FOUGHT the voice with positive statements that were the exact opposite of what it said. So, I literally told myself by speaking “out loud” in my head: “I am cool. In fact, I’m awesome.” And then I listed the reasons to myself: “I’m smart, funny, good looking, and I’m amazing at guitar, and I write awesome music.” And that was enough to make me feel 20–30% better. That’s how it starts. You chip away by battling that little voice, every time that you have an opportunity. Rejection and heartbreak. Those are your opportunities, and I really mean your only opportunities to break your insecurities. How else can you fight the little voice if it’s not showing up?

Everytime one of my friends comes to me with jealousy, or rejection, any negative feeling that is rooted in their insecurity, I always circle back to this story, and they always end up asking me: So, what’s your process? Now you know. Sure enough, a few weeks later, they start to tell me: “I finally discovered the little voice..I heard it when I was…” etc. Now, don’t expect to feel 100% better the first time you try this, after finally discovering the little voice. That’s why I call it chipping away. For me, it actually only took about 3–4 months to feel completely resolved, and finally free my confidence. I ended up with my first real girlfriend when I finally applied my new confidence to my dating skills. I didn’t make myself too available in the beginning stages of a new relationship. I didn’t ask when the next date would be while already on a date. I didn’t stop talking to other women until something was definitively exclusive. That’s a huge one. If you put all your eggs in one basket at a time, you’re always going to feel that way emotionally and it’s eventually going to show. I don’t want to turn this into a dating article though, because I really just want to focus on the process of training your brain to overcome repeating negative emotions. It truly saddens me the most when my friends come to me with these repeating negative emotional cycles and can’t seem to get out for the life of them. I’ve explained this process too many times, so I just had to share it with more people and get the message out there. If you’re reading this, there’s a good chance you have unresolved insecurities. Don’t be taken aback by this, because it’s just you and your thoughts reading this right now. It’s literally you and your internal voice. All I’m here to tell you is that it’s worth it to take a look at them. I’m now strong in my knowledge of my value, and I don’t rely on others to acknowledge it. I hope you’ll stay alert for that little voice, and give it a shot. I’m really glad I did.

07–27–2016 I’m now happy to report that I am a fully fledged dating coach. My clients all started by simply scheduling a 30 minute skype call with me here where you can pencil yourself into my schedule: https://calendly.com/evanmagor

--

--