06/29/2016 09:25 am ET Updated Dec 06, 2017

ADVICE 27: Should I Tell My Crush How I Feel?


Photo Credit: Brent Stoller

To send in a question, please complete this short Google form. All submissions are anonymous, even to the author.


(Questions have been modified for space and clarity.)

I am 15 and studying at a boarding school in Edinburgh. My school is all boys, so we have socials with girls' schools sometimes. At one of the socials, I went along with my friend and sat at the same table as him. His girlfriend was at the table and a few of her friends were there too.

It was meant to be a quiz night and a disco, but I couldn't concentrate on anything during the social, or even after on the way back. My whole mind was occupied with this one girl that I saw.

Her name is Jenny. From the first second we sat down at the table, I had my eyes set on her. I couldn't stop thinking about her and even when I was back at the school, all I could think about was her.

I had the number of my friend's girlfriend...we used to chat quite a bit. We eventually started speaking about Jenny and I managed to get Jenny's details.

I texted Jenny and we spoke for a bit, but I must've done something wrong, because after that, she made it clear -- or at least that was how I saw it -- that she didn't like me. She hasn't texted me since, and I always feel like sending her a message or telling her something, but I never end up doing it, not knowing what to say and feeling nervous.

We recently had another social. As I walked in, I passed her, and although I tried to avoid her, thinking that she doesn't like me, I couldn't resist looking at her. I am sure she looked back at me, and I feel like she looked over at me a few times throughout the event.

I really want to speak to her and tell her how I feel, but I don't know how or what to do. I always think about her, and this is driving me crazy. Please help me.
--Confused; Edinburgh, Scotland, United Kingdom

I'm happy to (try to) help you, because I've been you.

There's just one thing you said that I can't shake: "She made it clear -- or at least that was how I saw it -- that she didn't like me."

What exactly did she do? And are you sure you interpreted whatever she did correctly?

Having been in your situation, I know that when you're infatuated with a girl, part of you never believes that the girl could share your interest. You muster the courage to talk to her, but inside, you're always bracing, convinced that rejection is coming. So you process everything she does (or doesn't do) through that negative prism. I'm wondering if that's what you're doing here.

It's very possible that Jenny is not into you. She might have even come out and said it. If that's the case, you have to respect her feelings.

At most, you could let her know how you feel nonconfrontationally, like in an email or text, a message-in-a-bottle sort of thing. This would allow you to express yourself without putting her in too awkward a position. Just make it clear that you expect nothing from her in return.

On the other hand, there are some indicators that all might not be lost. For one, Jenny authorized her friend to give you her number. Girls don't do that unless they're at least open to hearing a guy's sales pitch.

And I wouldn't put too much stock in the fact that she hasn't texted you. It's possible she's waiting for you to take the lead again.

Also, at the second social, she was maybe/possibly looking in your direction on multiple occasions. Was she looking at you because she was worried you might be looking back? Or because she was hoping you were?

Hard to tell. One resource you could consult is your friend's girlfriend. She's close enough to Jenny to be giving out Jenny's phone number, meaning she might be privy to inside info.

Of course, you don't strike me as the type who needs a middle man. You've got Jenny's phone number, so why not use it?

There's no need to do anything dramatic, like professing your love for her or telling her that she's all you think about. That's only going to scare her off.

Instead, take things slowly, and let her dictate the pace of interaction. Send her a "How's it going?" text and see what happens.

Nobody knows what's truly going on here, which is why I think it's worth further investigation. And while the prospect of rejection can be terrifying, if you do decide to contact Jenny, what's the worst that can happen? That you end up in the same spot you're in now?

COMING FRIDAY: Talking Politics

Need more ADVICE? Check out the most recent installments:

ADVICE 26: Surviving a Long-Distance Relationship

ADVICE 25: I'm Dating a Married Man

ADVICE 24: Love Hurts

ADVICE 23: Loyalty, Jessup and A Few Good Men

ADVICE 22: The Two-Pronged Approach to Handling Stress

ADVICE 21: The Pitfalls of Infatuation

To send in a question, please complete this short Google form. All submissions are anonymous, even to the author.