How to Ask Someone Out

A written poem by Clare McCallan

As the reigning queen of Subway Love Stories 

(patent, pending, 

title, hard-won)

I want to talk to you, 

young men,

about how to ask out a lady on the train.

And young ladies…

let’s talk about how to get asked out on the train.


Maybe for you it won’t be a train or a bus,


You can go ‘head ‘n adjust,


To wherever your crush, is

Me? I like boys on public transportation 

But I’d encourage you to use your imagination 




Christians tend to take dating


But I’d say since the only requirement for a love story is love and a story…

you might as well write a story worth loving. 



The first step!

Comes way before you ask the girl out. 

It’s like any sport, 

You’ve gotta build muscle before you get on the court

You’ve gotta build confidence before you get on the court 

You’ve gotta –

Stop watching porn.


Ohh, too blunt.

Too, uncomf-ortable,

But if you don’t do the hard thing nobody else will, 

For you.

I’m saying this because I care, for you.

Porn is contributing to your body-dissatisfaction

Your inability to approach women

And your insecurity about your emotions.

Hey but maybe,

 you don’t watch porn though.

And for some reason your confidence is still low.

Well here’s a solution – 

Ready? Write this down:

“Self-confidence is the result of keeping promises to oneself.”

Make a promise to yourself 

Make a grooming routine

Make a workout routine –


Should you achieve,

This higher self-esteem.

Well now it’s time to,



Here’s what you’re gonna do. 

You’re gonna say


I’m kidding, 

Do not do that.

Introduce yourself like a 


And compliment something about her,

That she was hoping someone would notice. 

Big earrings

Funky shoes

A new tattoo 

Use your brain, big guy

Don’t let life pass you by. 



So ya wanna get asked out. 

Fair enough. 

Me too.

Well here’s my advice:

within the parameters of decency, 

dress like you like yourself. 

Like you like your body 

and your hair 

and your eyes 

and yes,

even your thighs –

Because you really should.

It’s worth liking. 

Just ask, 


Wearing all black doesn’t just make you look slim.

It makes you look like you’re in mourning.

I’d rather see you in glory.

You are glory.

You are color.

BE color.

You CAN pull off red lipstick. 

Everyone has a shade of yellow they can wear.

And you didn’t buy heels just for them to collect dust back there.

Allow yourself to feel joy and creativity in presenting yourself.

Give yourself permission to like you, 

And I promise, someone else will too. 

And my goodness, smile.

Think of it from the guy’s end –

Would you approach someone who didn’t seem happy?

With themselves or the world?

Look at me, you colorful, glorious girl:

“Self-confidence is the result of keeping promises to oneself”.

Promise to treat yourself the way you would a vase. 

Fill it with color and nutrients of substance. 

Color it with excitement and not reluctance.

You were built for adventure.

See this as adventure. 

And above all, be kind. 

It’s ok, to decline.

But do it with grace.

No snickering with your girlfriends after and telling everyone just to boost your ego. 

Just, be cool.

And…good luck!