Should I ask her out?

Oh mystical fortune cookie, I need help. I am falling in love with a beautiful young lady who I want nothing more than to have be my girlfriend. But I’m afraid—afraid that if I tell her that I really like her she’ll say no, and hate me, and never want anything to ever do with me again. I’m also afraid that she’ll never know, and I’ll be stuck in this awkward “admire from afar” place for forever and a day. What do I do? Do I tell her and risk rejection? Or do I stay silent and lonely forever? help


Go ask her.

09-13-40-52-54 / 34


Hello Diner. The answer to your Order depends on which lady you’re referring to. I see two: the one you describe and the woman everyone sees. More on that second person later.

You write of a beautiful, but rather ruthless person. In this universe of black text, either she dates you or she hates you—forever. If she isn’t your girlfriend, you suffer either unrealizable hope or exile from romantic love—forever.

I see your dilemma, Diner, and I’m glad you’re leaving such a dire life-changing decision to me, your dessert. I’ll do my best.

If she really is this ruthless beauty, run away quickly. Anyone who can be driven to such abject hate just being asked on a date will be a scary, unhealthy partner. Allow me to explain:

Picture a dinner party.

“Do you want the mashed potatoes or the broiled ones?” your host asks, holding up two pans.

“Mashed please, but HOW DARE YOU OFFER ME BROILED POTATOES! I HATE YOU! DON’T EVER SPEAK TO ME AGAIN!” your girlfriend shouts.

She flips the oven-hot pan. The broiled potato spears brand third degree burns onto your host. The permanent scars now serve as a reminder for that evening’s transgression.

You see why I’m worried?

The only reasonable justification for her being upset with you for asking her out is if she has already told you she doesn’t want to date you. Instead, the woman everyone else knows would have a more sane and logical response: yes, I’d love to or thank you, no. She would still be the person you know, and would still want to be your friend. I highly recommend asking that person out.

Rejection is a risk, but it’s one with very minor consequence. By not asking, your fear is making the decision for the both of you: you’re choosing to reject her until she asks you.

Whatever you decide, your anxiety is distorting both of you into completely different people. The woman that everyone knows is not a ruthless person that will shun you forever. She may, very possibly, like you back.

If she doesn’t, your mind will get used to the idea and move on. We talk about that process in this Fortune. You are not an unlovable person who will never find a partner. If this woman sees an incompatibility between you two, it will only free you to find someone more suited for you. Look past her beauty. Trust her judgment. It’s only appropriate if you’re already trusting her with your heart.

If anything, it’s your anxiety that needs scrutiny. Look at how it’s affecting the way you see everyone. Your anxiety makes your friends seem like cruel monsters, and it’s telling you that no one will love you. Yet you trust it unquestioningly. Your anxiety is the true ruthless, unloveable monster that you need to confront and remove from your life forever. I hope your friend will stand with you to face that challenge. Good luck asking her out, Diner.