Dear Dana: I’m Too Shy To Talk To My Crush…Help!

Dear Dana is a bi-weekly advice column for humans who engage in romantic relationships. Please send your dilemmas, issues, conundrums, assumptions, conflicts, anxieties, worriments, obstacles, complications, predicaments, queries, questions, and any other synonyms for “problems” to

Dear Dana:

I’m an almost-17-year-old girl, and there’s this guy in the grade above me who used to stare at me a lot. Even when I would look at him, he wouldn’t stop and I thought he just had a staring problem. Then I started to develop a crush on him, but I never showed it.

Then one day he came and sat down with me and my friends and asked us a question. My face immediately turned red and I didn’t hear what he said so I just kept quiet. My friend looked at me to answer him but I just stared blankly at her with a red face. I then made her answer and after she did, no one said anything so he just said “thanks” and got up and left.

Then a few weeks after I started to notice that he didn’t stare as much and wasn’t around me as much anymore. I’m really shy, so whenever I make eye contact with him I look away. Once, I saw him at the bus stop and looked at him, he started to smile at me but I looked away too quickly.

I want to talk to him, but I’m so shy and turn red so quickly. Also, I would not know what to say to him.

So what should I do?


Shy Brit


Dear Shy Brit,

I want everyone to know that your original email was about three times as long as this edited version and full of many instances when this boy stared at you while you simultaneously avoided eye contact / considered falling in love with him.

I have had several long and passionate love affairs with men who were completely unaware of our relationship. When I was in high school I discovered a beautiful boy in my Algebra 1 class. He had dark, wavy hair, he was tall, and had these blue eyes that held me in their stare. I noticed him looking at me one day, and then I started looking back. I would yawn and watch him out of the corner of my eye to see if he yawned too, to see if he had been looking at me. Then, I started to start the stares. I would look at him until he noticed me, look away, smile to myself, and then glance back to see him still there, still staring at me. When our eyes met it would make my stomach flip and my knees liquefy. I hated math but I lived for this math class just so I could blink flirt with my eyeball boyfriend again.

One day, we had to work in small groups and he and I were assigned to work together. I was so incredibly excited to have an excuse to talk to this boy. And he was excited to see me too—he slid his desk right next to mine and immediately asked if I wanted to see the drawings in his notebook. Oh my God an artist! I am in love. And he opened his notebook and showed me multiple detailed drawings of our math teacher, guns, and our math teacher being shot apart by guns. He giggled as he showed me the pictures and made rat-a-tat-tat machine gun noises. I sat there, quietly, not speaking, trying to hide my disappointment.

He was an idiot and our love was dead.

It is very romantic to make long distance eye contact all day long. It gives many of the benefits of being in a relationship—you get the anticipation of hoping to see him, the adrenaline spike of catching sight of him, and the reverberating rush of him looking at you and smiling. The difference is that instead of feeling those endorphins and then amping them up by speaking to him, you panic, turn red, and leave.

You feel as though you are in a relationship with this boy. But you aren’t. All of this staring/not staring is pretending. You’re enjoying the rush of flirting without the risk.

Did he come over to ask you a question because he likes you? Maybe. Or maybe he just had a question. Did he stop looking at you as much because you don’t flirt back and he isn’t sure if you like him? Maybe. Or maybe he alternately stares/doesn’t stare at everyone. The only way to know for sure is to talk to him.

Talking to him is scary. Very scary. But, like your fake relationship with him, it’s fake scary. Because you need to know that if you do walk over to him, and you do say something, he will say something back. And then you’ll say something else. And you’ll make incredibly awkward small talk for a time until you find something you have in common—a teacher, a class, a sport—and suddenly you’ll be actually conversing, communing. You’ll be talking to the boy you like and it won’t be terrible. You’ll be having kind of a nice time.

But I’m not telling you to go talk to him. When you find yourself having long love affairs with people without ever speaking to them, it’s an indication that you don’t actually want a real relationship. Either you’re not ready for it or not willing to undergo the risks associated with being emotionally and physically vulnerable with another person. And at your age, there is nothing wrong with having love affairs all in your mind. This is the reason that boy bands exist, to give young girls the ability to express romantic feelings without having to actually clumsily engage with real life boys.

The media makes it seem that all teenagers are forever making out under the bleachers and falling in love and going skinny dipping and making increasingly poor and sexy decisions. But in reality, teenagers are usually sitting at home with their parents. Teenagers don’t tend to have incredibly rich and fulfilling love lives. Teenage years are a monsoon of hope and awkwardness. You think you know what you want, but maybe you don’t, but you should talk to him, except what if he doesn’t like you, and you totally like him, you really like him now, you’ve convinced yourself that he’s your everything until he opens his mouth and says something and ruins it.

It’s OK to be shy. It’s OK to be sensitive. It’s OK to turn red and not know how to talk to the boy you like. It’s OK to be protective of yourself. It’s OK to want a boyfriend but have no idea how to make a relationship with a boy happen. It’s OK if you want to be in love but also are afraid of the emotional risks that come with such an intense connection with another person. You have the entire rest of your life to spend in active relationships.

For now, just enjoy the rush of adrenaline and pulse-pushing hope that comes from him approaching you. For now, let yourself relax. Stare back at him, smile, and know that you don’t have to do anything else.

Dana Norris once went on 71 internet dates, many of which you may read about here. She is the founder of Story Club and editor-in-chief of Story Club Magazine. She has been featured in McSweeney’s, Role Reboot, The Rumpus, and Tampa Review and she teaches at StoryStudio Chicago. You may find her on Twitter at @dananorris.

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