Once during freshman year I was in my room doing homework and I got a text. It was from my friend, who was on a date, asking “Should I put my arm around her now or half an hour into the movie?”
At first I thought, “Is this guy really that stupid?” I imagined him sitting in the dark movie theater, leaning over and secretly texting me with his phone poking out of his pocket while the movie trailers were going on. A few seconds later I replied, “When the movie starts.”
He texted back, “OK.”
In eighth grade, my friends started asking me for advice with girls. By my freshman year, I became the guy who gave relationship advice to other guys because by then I had dated five girls. Some guys I barely talked to would message me on MySpace or AOL Instant Messenger asking me for help. But I didn’t want to be the relationship-advice guy. What if I gave my friends advice that would completely mess things up? The way I saw it, just because I had dated some girls shouldn’t make me seem like a dating expert. I’m not Mr. Confidence. But I know some basics: don’t use cheesy pick-up lines (unless of course, you’re trying to be funny) or write bad poetry. Just relax and be open to trying some new things.
Now that I’ve given advice that has helped my friends, I’ve become more comfortable when my friends ask me for help because I’m confident that I won’t screw them over.
So whether you’re a guy who needs a few pointers or a girl who wants to know what a guy is thinking when he’s trying to get to know a girl, here are the three most important pieces of advice that I’ve given to anyone who has asked me for help.
ADVICE: While being friends first is good, don’t date your best friend.
My “romantic adventures” started in eighth grade. On a school trip to Washington, D.C., I spent a lot of time—on the bus rides, at monuments and at restaurants—with one of my best friends, Angela. Even though I was already great friends with Angela, I ended up spending more time with her than I ever had back at home. So toward the end of the trip, I thought about asking her to be my girlfriend.
On the second to last night of the trip, my best friend Niko and I went to the hotel lobby to get hot cocoa. Angela was there, too, and she and I started talking by ourselves.
“I’ve spent so much time with you,” I said while trying to keep my voice from shaking, “that I feel like I’ve gotten to know you better in this one week than in the last year and a half. And I know we’re best friends but I feel like we could really make this work. Will you be my girlfriend?” This was my first time asking someone out. I had to put the cocoa down because my hands were shaking so much.
She gave me her signature smile and said “yes.” Then we hugged for like 15 seconds while I smiled from ear to ear.
But since we were still in middle school we didn’t act like an actual couple. We never held hands at school, and our only date was a triple-date with two other couples. In fact, I never even kissed her. The one time I tried to kiss her cheek, I was extremely nervous, so I closed my eyes and just threw my lips toward the side of her head. I got her ear, but hey, it’s the effort that counts, right?
Nothing seemed to go right dating-wise. Every move I tried to make, whether it was putting my arm around her during our movie triple-date or even texting her, I just didn’t feel as comfortable as I did when I was just friends with her.
I had assumed that we would become closer once we were a couple. But it wasn’t possible for us to get any closer. In D.C., we spent three to four hours a day together, just the two of us hanging out. When we got back to school we spent only two hours a week together and that wasn’t even one-on-one time. When we were best friends we hugged randomly and it always felt natural, but once we started dating I felt required to hug her every time I saw her.
After about a month we broke up. I don’t even remember why. I just remember that I was really angry at her and she was mad at me. The weird thing was that we didn’t argue at all when we were friends. I think we both kind of knew that we were better off as friends and to this day Angela and I are friends.
ADVICE: Text messaging or instant messaging is the best way to get to know a girl.
If you want a girl to notice you, you should start by texting and instant messaging her. That’s how it went with my current girlfriend, Jinny.
I thought she was cute so one day as everyone was taking their seats in class, I said, “Hi, Jinny!” and smiled at her. She looked up and glared at me. I still thought she was cute, so I wanted to find out why she didn’t say hello back.
The next day I started cracking a few jokes in class and Jinny laughed. And that’s what I wanted, for Jinny to see me as a relaxed guy. That way when I asked for her number it would be more of a friendly thing than a dating thing. A couple weeks later she gave me her number. From there, I knew I had to do one thing to truly get to know her better: text.
My first text to her was a simple, “Hey there!” For the next few days I texted her, “So what’s up?” Maybe it was annoying, but it did two things for me. One, it helped me get a better sense of what she liked to do with her free time. Two, it showed her that I cared about what she was doing and that I was interested.
I always wondered if she was spending as much time thinking about me as I was thinking about her, so I texted her a lot. We ended up texting about 100 times a day. We talked about everything—classes, favorite foods (I found out that she literally loved everything), her extremely fast metabolism, our goals and dreams, our childhoods.
Eventually we started talking on the phone and I discovered a personality trait of hers that made me really fall for her: she listened. She was always open to learning new things, so even though she had no interest in sports, she would always listen to me whenever the Lakers were the only thing on my mind. She even asked questions, which would lead me to giving her a whole history lesson on whatever sports subject I was talking about.
After about three weeks, Jinny and I had developed a friendship, but I didn’t have enough confidence to flirt with her in person. So, I decided to be flirtier when I texted. One day I pressed the keys on my phone to spell: “Haha you looked really nice today! (:” Sent. Happy face and all.
After my phone’s screen flashed “Message Sent,” I started cursing and calling myself stupid for sending it. I yelled, “I rushed it, didn’t I?!” I beat myself up for two minutes until my phone vibrated.
“Thanks! (: It took me all night to pick that outfit … Glad that someone actually noticed …”
I went from thinking, “Kevin, you’re so stupid,” to “Kevin, you’re a genius.” After that, I I complimented her a lot more and two months after I sent that first flirty text, we started officially dating.
ADVICE: If you’re attracted to two girls, go with the second one you started liking because you weren’t into the first one enough to like only her. And dating both at the same time is just wrong.
Things started turning bad with my former girlfriend Katelin during the summer before ninth grade, because she wasn’t part of my group of regular friends.
But there was a bigger issue—Kristine. While Katelin was really cool and outgoing, I really liked Kristine because she was not only cool and outgoing but was also a sports fan. We had some amazing conversations about the Lakers, the Dodgers and college sports, which I never had with any girl before. I got the vibe that Kristine kind of had a thing for me too.
Even as I started having some feelings for Kristine, I still dated Katelin. Those dates were torture. Instead of having a good time and giving all my attention to Katelin, I would constantly ask myself, “Should I really be here right now? Am I with the right girl? Am I leading this girl on by dating her even though I like someone else? What am I doing?!”
It came to the point where I had to think about the situation for a good three or four days. I decided that if I really liked Katelin, then I wouldn’t be thinking about Kristine. So a couple days later, I called Katelin to tell her that I didn’t have feelings for her anymore and that I had feelings for another girl. I felt like an a-hole, but Katelin told me that she appreciated my honesty and that she was happy that I told her instead of leading her on. I ended up dating Kristine for about eight months.
I know there are people out there who are having trouble with dating. Trust me, I’ve been there. I wanted to write this article because I used to be the guy who didn’t think he could ever get dates with girls. But I’m here to tell you that it’s possible to get a date with the girl of your dreams!