Disclaimer: This advice column is for entertainment purposes and no part of it should be taken seriously. Dr. Cupid is not a professional or an actual, certified Doctor.

Dear Dr. Cupid,

I’ve been hung up on the same person for years– since sophomore year to be exact. I’m a senior. Teenage love is a tricky thing, it’s trickier when the person you’re in love with is your best friend. Several of my friends think that my crush feels the same way, but I get constant mixed signals. 

I feel like I have two options. One: Tell them how I feel and risk them full-on rejecting me. But I want to stay friends with this person and I’m worried that telling them would make things too messy if they don’t feel the same way. 

Two: I could keep it bottled up like I have for this entire time. Not the best feeling, but at least they’re still in my life without the complications of trying to take things further. 

What should I do? 

All the best,

Broken-hearted Best Friend

Dear Broken-hearted Best Friend, 

Being “hung up” on someone for two years sounds sweet but is actually unbearable and a little pathetic, no offense. If you graduated without telling them how you felt, I’d call you pathetic with full offense. 

You know the potential consequences of both your options, but I’ll remind you: Regret or embarrassment. I say embarrassment, not loss, because if this person is your best friend, you won’t lose them. I promise you, Brokenhearted best friend, regret lasts for years while awkwardness in a friendship will last for a few weeks at most. 

You could test the waters by making this person feel special– compliments, thoughtful gifts, all the works. The way they take these gestures will be very telling of their feelings for you. 

If you’re tired of waiting, though, I don’t blame you. Maybe I’m a little biased– I always advocate telling someone how you feel, because how serious are the consequences when you’re graduating in just a few months? How serious are romantic consequences ever in high school? God, just tell them already. 

Happy Valentine’s Day, seize the day!

Love, 

Dr. Cupid?