I may have made a terrible mistake,

but I look hot.

- Today, we're trying heels.

- We are gonna be going through the gauntlet.

The high heels gauntlet.

- We're going to dinner, we're going to bars,

and we're going dancing,

and were gonna wear heels the whole time.

- We're having ourselves a night.

- [Ned] What advice do you have for us?

- Don't.

- I love high heels.

I think they looks fabulous on women,

I think they look pretty damn good on men.

- It totally is hot, right?

- [Ned] Heels are like a fun, fancy thing

you get to do when you go out.

- I fucking hate heels.

I'm a shorter man,

and when girls wear heels around me,

it makes me shorter.

I shrink and they get taller

and I get shorter.

You pop on four extra inches, guess what.

I can't compete with that.

Alright, lets try on these torture devices.

- I feel like the best part is actually,

even before I go out,

and I'm like, "Yeah, I look good."`

- I'm wearing ankle boots.

They have a zipper along the side.

I actually think they're really cute.

I don't know that I can put this on.

I would have to sit.

I'm just trying to get home without a broken ankle.

Okay, not so bad.

- I would wear this.

- [Becky] Yeah - [Ariel] 100%

- [Becky] Have worn this.

- Not stilettos,

wide, wide base.

♫ Who's that man

♫ Walking down the street

♫ With those delicate feet

♫ It's Zach.

- For tonight, I wanted to show off a lot of my foot.

My fiance painted my toe nails.

I have chosen a little black strappy heel.

I've never had a buckle so tiny.

Three inches tall.

Aww! You can only see four of my toes.

Why did I paint all 10 of my toes,

if you can only see about seven.

- I would wear this to an eighth grade dance.

- [Keith] I feel pretty fucking hot.

- When we did the drag video,

I had on boot heels.

That doesn't count.

So tonight, I'm gonna wear stilettos

for the first time.

- I get platforms or wedges.

There is nothing else.

- Okay.

Keith,

would you be a dear

and give me a shoulder to...

- Of course.

- Yes, thank you.

(chuckling) Oh.

- I got you.

- This is Ned's heel.

A four inch, silver sandal,

that looks...

- It looks like it came straight out of my closet

10 years ago.

- But does it make my butt look good?

If Ariel does decide to wear heels,

I set a timer.

Three hours later...

- I either have to sit down,

or I have to go home.

- I don't think Ned's gonna last more than an hour.

- Oh man, I don't like Christmas,

but I do like unwrapping stilettos.

High heels for me, are just a part of fashion.

My heels for tonight,

are actually called dagger pumps

because the stiletto is so tall,

they'll mother fucking kill you.

Yeah, I can't even stand on my toes as high as these.

Oh shit.

Maybe this is a mistake.

Ow!

- That's upsetting.

- I don't think I've ever seen a shoe that big.

- This is Lady Gaga.

- Where would I see these?

I'd see these in a show.

Where would I wear these?

I wouldn't.

- What do you think is gonna happen?

They're fucking daggers.

(dance music)

- Bring band-aids.

- Bring flats.

- Instead of tapping out,

we're going to be flatting out,

and that's when you decide to put on your flats.

- Eugene, he's already started to damage the apartment.

- Wonderful night. - The dagger strikes!

Let's fuck tonight up.

(hip-hop music)

- Mm mm.

- [Eugene] We leave my house,

and immediately, I realize

that walking is nearly impossible.

- [Zach] Even just in getting from Eugene's house

to the restaurant, a lot of us are getting cranky already.

Ned is just, like, the hangriest I've ever seen him.

- I'm getting very impatient, very quickly.

- We actually get out, and I'm like,

this is not practical.

- [Zach] First we go to dinner.

- Dinner is sitting.

Sitting's great.

- [Eugene] We're out at dinner, we're having fun,

Ned got his food.

You got, fucking, two entrees?

- I was hungry!

You can't tell me what to eat

when I'm wearing heels.

- This is not the worst yet,

but it's only been a few minutes.

- The worst part of wearing heels,

is actually walking in between places.

- There's no seats while you're walking down a sidewalk,

and our first bar, super close, right?

Just had to cross the street.

It was like, maybe, half a block.

It took us nine minutes to get there.

- That's how far away it was?!

- It's literally across the street.

- [Keith] I mean, it's basically like

watching toddlers on ice skates, right?

We get to this steep incline,

where the sidewalk goes to the road,

and it's just so steep.

Who designs these fucking sidewalks?!

- [Zach] There's a lot of uneven terrain, but

we're at the first bar.

Time to partay.

- The best thing is when you walk in,

for the first 10 minutes.

You feel incredible, you feel like you look incredible.

- As much as this hurt,

I recognized that when I stood in those six inch stilettos,

I looked fucking hot as shit.

- But, I'm getting hit on like crazy.

I'm so much taller than normal.

- Me too. - So are you.

- [Keith] It was fun though,

I loved the attention.

- [Ariel] It's a great 10 to 15 minutes.

- I don't think I'm gonna last the whole night,

so I'm doing my dancing now.

- And very soon, we were all sat at a table.

Ned linked both of his heels on the stool

and then as he stood up to leave.

- My momentum's going forward,

but my heels are stuck on the stool,

and I just go, "See ya!"

Man down!

Man down.

- He fucking face planted.

Like, bam!

It was hilarious.

- But, the bartender is, like, holding my drinks back,

thinking that I need to be cut off.

Nope, not wasted,

just wearing heels.

- We are now done with the first bar,

we are now heading to the second bar.

- Ariel is doing something for me,

which I always do for her.

- You know, my biggest nuisance

has always been that we aren't walking fast enough.

- Your biggest, what?

- Nuisance.

You've never walked this slow.

- I haven't.

- I look good, I feel good,

I'm taller.

- [Ariel] Zach's shoes are the best,

'cause you have a protective layer,

all enclosed.

- [Becky] Ned and Kieth, however,

are at risk for being stepped on

because their toes are exposed

and they're low to the ground.

- Somebody bumped into me

and stepped on my toe.

Ow!

God!

He said, "Welcome to the real world."

Oh!

- [Zach] We get to the next bar.

I'm looking hot,

and my friends are fucking sitting down.

- I just want to go home now.

25 minutes sitting, I move to dancing.

That's my game.

- The heels are not hurting me yet,

but I'm forward thinking man,

I'm responsible.

So, I'm gon' get drunk.

- When you drink, it distracts you from the pain.

- There's a pool table,

and if anybody knows anything about pool,

it's all about bending over and sticking out that tush.

Pop that booty.

And, when you've got heels,

that tush has got the push.

The drinks are hitting,

and that means it's time to dance.

- Dancing usually happens towards the end of the night.

- It's fun to dance on the floor.

- Eugene starts, not only dancing,

but getting down harder than I've ever seen a man

get down, in my life.

- There's a weird feeling

that in the heels, I wanted to impress people more,

so when I was challenged to dance,

I mother fucking danced.

- [Zach] He's wearing literal daggers...

- And it did not feel good.

- What is happening?!

- I'm taking the tiniest little steps

I've ever taken in my life.

- [Becky] Are you looking at the ground?

- Honestly, the wort thing

about wearing heels out for a long time

is feeling like a burden,

and so I try to grit my teeth and bare it,

which mean that my toes bleed.

- [Zach] I turn around, and half of the group is gone.

Keith and Ned are dying.

- My feet hurt!

I'm done with this!

I do outside, I stand by a dumpster,

and I take off my heels.

Oh man.

(chuckling) Ho ho ho ho ho!

Oh, that feels so good.

- [Zach] The look on his face was just pure bliss.

- Just fuck those things, they hurt.

- At this point, I've fallen over,

I've gotten stepped on,

I've gotten cat called, and

honestly, my night is over.

I don't even care if I don't have flip flops!

Oh my God, it feels so good!

- [Keith] Your feet are on the dirty ground.

- Oh, my feet are on the dirty ground, but I don't care!

My toes were like, "Ahh!"

- It's like all your stress is gone,

except, my feet still hurt!

- We should grab those shoes, though,

they were expensive.

- The final walk we had to make

was between the third and fourth bar

after Kieth and Ned leave.

Alright, only the hot ones are left.

Let's do this!

It's just not even funny anymore.