• Season 1, Ep 10

sneak peek: Dating a Gangster

A regular guy ends up on a date with a smooth criminal.

03/08/2016 ยท 3:38

>> I'm a pretty

conservative guy.

I work in an office job,

do what I'm supposed to do.

I met this girl.

This girl was like L.A. Hot,

curves in all of the right

places, skin glowing like she

lives on the beach so when I

line up this first date I want

it to be real, real classy, but

I get there the place is packed

from wall to wall.

It was St. Patrick's Day and we

sat down, I use my go to line,

"So, hey, how you doing?"

"Oh, I'm good, I'm good."

"No, I know how you look, I

asked how you're doing."

"Stop it."

Every time she speaks I'm just

trying to look straight into her

eyes like I am all the way

listening to you, but we're

sitting in front of empty

glasses and the server is

nowhere to be found and my date

looked at me and she was like,

"Well, why don't we just leave?"

"Um, um, I'm sorry, what?"

"People dine and dash all the

time, why don't we just drink

and dash?"

The black guy alarm in my brain

is at full blast.

I'm from the south side

of Chicago you don't walk out

on a check.

"You're so funny, like--"

"What are you scared?"

"Ha, you're so-that's--"

"Don't be a bitch."


>> I just kind of sat there

because she got up and walked

away like smooth criminal and

somehow I completely lose

control of my legs and stand up

and follow her out.

And it was the longest walk of

my life, I was so afraid.

We get outside.

Every time she looks away from

me I'm trying to flag down the

valet dude like, "Yeah, we're

the one-the blue-yeah--" She's

peachy keen just, "Yeah, no the

drink actually wasn't bad."

We get in her car and she gives

me a ride back to where

I'm parked."

We pull up to this spot

and this is the part of the date

that I'm worst at.

You know I don't know whether

it's time to make out

or get out.

She just takes the reins, dives

over the console, is straddling

me in the passenger seat and

we're making out, going at it.

The windows are fogging up, the

car is rocking, shirts going

this way, pants this way, I'm

naked and it's about to go down.

I look up and it's a police


"Uh-uh, nope!

Not tonight!

Not on my watch!

Wait right here."

And he starts walking back to

the car presumably to get a

citation and throws me in jail

for 25 to life.

I'm going to lose my job, my

parents are going to kill me,

and I'm not going to be able to

afford this.

"Uh, uh," I look up, this girl

without taking a beat, without

throwing a single thread of

clothing back on dives between

the seats ass naked, starts the

car and just peels off like a

professional NASCAR driver she

hit the corner, bent around.

I'm sitting in the back like,

"Let me put my seat belt on

before you start doing all this


She's whipping down the block,

goes around one parked car, hits

the right, we go down the block,

she pulls into somebody's

driveway cuts the car off,

"Get down."

And I just real quick slid and

just tried to get as little as


>> [imitates heartbeats]

>> You can hear the drop of

sweat come off of my face and

hit the seat and the cop drives

past one time--

>> [imitates heartbeats]

>> The cop drives by one more

time and she goes, "Okay,

I think we're good."

Just shrugging like it's no

big deal.

"Oh my God, like, I'm so sorry.

I never do anything like this."

"You definitely done this

[bleep] before.

Like you were the 007 of doing

this [bleep]."

I was definitely freaked out,

you know what I'm saying?

"So hey, I should probably

get going.

You know, I have work."

"Yeah, well, call me."

She drives off a lot more calmly

than she did when the cops were

behind us.

I'm limping back to my car, you

know, blue balls and all trying

to decide whether I was more

afraid or more in love because

unbeknownst to me I had just

gone on a date with a gangster

and it was crazy.

>> [upbeat music]