S2 Shady Moments - Jack & Will | Will & Grace
1 Video View·Apr 27, 2026
I'm gonna say this because I love you.
Your disproportionately large head gives you a marionette-like quality.
What do you think of my eyes?
Two words.
Major surgery.
The fact that you can see the white the entire way around the eyeball
makes you look, well, crazy.
And I say that with love.
Puppet head.
Crazy eyes.
Does this go with this?
Does no go with way?
Okay, you're no longer helping.
Out.
And I don't need you here doing a Jonah Melissa Rivers on me.
Oh, Sybil!
What's with the gloves?
Did the eczema flare up again?
Now, Will, I understand you're anxious
because Grace isn't here to dress you and burp you.
Oh my god!
The day I've been waiting for has finally arrived.
Congratulations, Jack.
I wish you a long, happy life as a woman.
That's so funny, I forgot you're fat.
It's Raven Man!
Night at the club.
Jack was in fuego all night.
The lovelies were buzzing around me like...
Like what?
Like moths to a flamer?
Actually, more like fat to a Willis fat.
Oh, touche.
You know what?
No, I'm not gonna do this.
Blind dates are a nightmare.
Always ends up being with some guy
who keeps yapping on about his two cats.
I spend the whole night trying to figure out a way
to get out of there by faking my own death.
Excuse me, Mother Superior.
It just so happens that I've met
many fine young lovelies on blind dates.
I'm talking about blind dates, not blindfolded dates.
That sounds fun.
What time is it on?
Not really looking for any Johnny-come-latelys.
Oh, please, please, please.
Can't I be a flouncing geek too?
I forgot to tell you that your mother phone left a message.
Guess what?
I've been promoted to captain at my catering company.
And tonight, I'm supervising an event
at the Waldorf Astoria.
I will have eight men under me.
How great is that?
What'd you do?
Write the Gay Make-A-Wish Foundation?
Could you just once reach into
that cold, black heart of yours
and say, congratulations, handsome?
Hey, handsome, look around.
I'm closing down my office.
I've lost all my clients, so you'll forgive me
if I'm not jumping up and down for joy
because you've now made head butter curler.
FYI, you SOB, cater-waitering is T-U-F.
F.
Oh, tough, yes.
All those years at waiter grad school,
the lectures, the all-nighters,
all to answer the eternal question
that has plagued mankind
since the dawn of consciousness,
chicken or fish?
Listen, mister, and I use the term loosely,
you can do my job for even one night.
Jack, a monkey could do your job
providing he had a tux and a lisp.
And the date begins now.
Hi.
Okay, let's stop right there.
First of all, why would you choose
to wear your fat jeans on a blind date?
These are not my fat...
I don't have fat jeans because I'm not fat.
How did I ever think this was a good idea?
Because I'm an expert.
Well, I go on literally thousands of dates a year.
That doesn't make you an expert,
that makes you an escort.
Well, good for you, Jack.
What's the video about?
It's a hard-hitting look at sexual harassment
in the workplace.
I'm sorry, Jack, sexual harassment?
Starring the guy that asked his co-worker at Starbucks
if he had two nipples for a dime?
Which, by the way, was the beginning
of a very fulfilling three-day relationship.
Couldn't you once be happy for me?
Hey, don't you think it's possible
that maybe I'm jealous
because you've got this great new job
and I've been unemployed for a month?
Oh, no, are you?
You're right.
Hateful!
I'm right in your closet.
They said dress like a repressed straight guy.
Yes, I'd like to speak to the president of NBC, please.
This is Jack McFarland.
How long will he be in the meeting?
Very fine, I'll call back later.
Hi, I'd like to speak to the president of NBC, please.
It's Julianna Margulies.
I have a cold.
Hello?
How do you stop unwanted homosexuals
from invading your office?
Claire?
Oh, my God, I finally get to meet
the best friend from high school.
Oh, my God, Claire Danes?
Yes, Jack, Claire Danes.
Did I not mention that 19-year-old Claire Danes
is my best friend from high school?
Uh-huh.
You're bloated.
I'm wasting your time.
I am outraged by this.
Why aren't you?
Because I'm realistic.
Clearly, nobody wants to see two men
kissing on television.
Not the network, not the viewers,
not the advertisers.
That's right, Will.
They want to pretend we're invisible.
Well, what about our constitutional right
to see two hotties get it on?
Would that be the constitution that begins,
we the people?
Why is there an earring in your sofa?
Probably Grace's.
It looks just like the skull earring
I gave my old boyfriend, Walter.
Uh, well, I don't know.
It looks like a pretty common skull.
I had a W engraved on it, you know, for Walter.
Isn't that sweet?
Oh, look, this one has an M.
Jack, it's not what you think.
You fooled around with my Walter.
Okay, it is what you think.
Jack, Jack, he wasn't your Walter at the time.
You broke it up long ago.
You know, he was, he was Walter up for grabs.
So I, I grabbed, you know.
How could you?
I, it was one time.
Commandment number one in the gay bible,
thou shalt not covet my ex's ass.
Jack, is that from the book of Genesis-y?
That is so funny.
That's it, goodbye.
Jack, Jack, sinner!
I think he realized he made a mistake.
So, how does it feel?
Good, it felt good.
Yeah?
Don't tell me, tell him!
Really?
If what's holding you back is your attraction to me,
I, I just want you to know it will never happen.
Okay?
Let that free you to pursue other lesser men.
Jack, there are no lesser men.
I'm meeting Rory at the Mandy Bar.
You remember Rory?
Yeah, he's the friend that never slept with any of my boyfriends.
Jack, if I'm supposed to stay away from every guy you've ever slept with,
that would leave me with women.
For your information, Will, Walter was the love of my life.
You said that about each backstreet boy at one time or another.
Besides, you guys only went out for, what, a month?
Yeah, and then he dumped me.
You remember what that feels like, huh?
It hurts.
I had no idea, you never mentioned it.
How often do you talk about Michael?
Oh, that's right, all the time because you're so self-absorbed.
Whoa, whoa, slow down there, cowboy.
A gentleman always eats like a lady.
And this is probably a good time to compliment your date.
Tell me my eyes are pretty.
The bug eye or the other one?
Okay, see, this arrogance is probably why your date with Charlie didn't work out.
I am not arrogant.
Yes, you are, you've been acting superior to me all evening.
That is not arrogance, that's scientific fact.
We had a great date, you know, we laughed.
He should have called me.
You see, there it is again.
What's behind that arrogance?
A layer of fat and fear.
Fear rolled in fat, wrapped in arrogance.
I am not arrogant and I am not afraid.
Then why don't you call him?
Could it be fear of rejection?
Of starting over?
Of opening yourself up to someone else?
What?
I think you may have a point.
For real?
In spite of your trying to help, Jack, you've actually helped.
You know, I appreciate how much you care.
Shut up!
I totally made out with that bartender.

