How to ask someone out when you’re terrified of rejection.

Outcast asks: I think I’m going to ask this girl to be my girlfriend. But here is the thing, I’m pretty much afraid of the outcome. I don’t think I can handle a rejection, especially coming from her. And I know I have to move on if that happens. But what happens if she rejects me? I know I sound negative about this, but someone once told me “to avoid disappointments, you must lower your expectations”

Hi Outcast –



I’m going to ask you to do something really weird.  I want you to imagine the moment of your death.


Not in terms of how you’ll die, or how old you’ll be.  I just want you to imagine that moment when, as we always hear, your life passes before your eyes.  Your joys, your sorrows, your accomplishments, your failures, your loves, your hates…  What do you think will matter to you the most right then?


Of course, I can’t know for sure, but I’ll bet that, when a person (or a dog) experiences that, one of the biggest questions is What Did I Dare to Try.


If a dog in the wild is starving, and tries to steal some food from a wolf, and is killed for it, at least that pooch tried to live, right?


If a person loves movies, and devotes decades of their life learning to be a filmmaker, and gets a movie made, but no one buys it and they lose all their money and have to get another job they’re not that excited by, at least they tried to make it in that world, right?


And if a little bug wants to eat an apple, and crawls all the way up a tree and out a branch, and just as she’s about to take her first bite of it, a bird flies down and gobbles her up, at least she tried to eat it, right?


Outcast, there’s a whole branch of philosophy called Existentialism, that argues that this is actually the meaning of life.  Not whether we succeed, but what we do, what we try, how we live.


I haven’t caught 90% of the squirrels I’ve chased, maybe 99.  So who am I?  I’m a dog who loves to chase squirrels.  And I like being that pup!


My human friend Handsome… well, he’s that failed filmmaker I talked about.  That’s his story.  And he’s still proud of how hard he tried.


And you?  You are completely smitten with this girl.  And because you’re so crazy about her, the idea of her rejecting you scares the daylights out of you!  Great! That’s what love, especially young love, has looked like for millennia!


And I really hope, when you ask her, she says yes!


But what’s important for you to realize is that, if you do ask her out, and she says no, you will at least know that you lived your truth.  You owned your passion.  You tried.  There’s an old saying “Better to have loved and lost than to have never loved at all.”  It’s really true.


Now I’m not doing all this talk about trying and failing to add to your fears.  What I’m trying to say is that if the very worst thing happens, which is that she says no, you still will have succeeded!


Look around you.  You’ll see person after person who didn’t take a chance, which they really regret.  They had an opportunity to travel, got scared, and have never left their home town since.  They got a chance to invest in something risky, didn’t, and it was a huge success.  Or, yes, they had the chance for the love of their life, choked, and lost that opportunity forever.


So I want you to try. And again, I really hope you succeed with her.  But if you don’t, I want you to know that you will still have moved forward in your life.  And one other thing – you’ll have learned that you can get that rejection and survive!  So the next time you fall head-over-heels over someone, you’ll have that much more confidence in your pursuit.


And if you need yet another boost, I urge you to find a recording of an old song called “Some Enchanted Evening.”  It’s a lovely tune, but it’s the words I’m especially interested in you adopting as a motto:


Some enchanted evening, when you find your true love,
When you hear her call you across a crowded room,
Then fly to her side, and make her your own,
Or all through your life you may dream all alone.


This is your moment, Outcast.  Define yourself as a brave romantic, and you’ll always know you are just that.


And, to quote another great song (this one from the singing group I was named after)… Everybody Loves a Lover!


PLEASE let me know what happens!


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