In this Valentine's Day special, licensed relationship therapist Jonathan Decker and filmmaker Alan Seawright take a retrospective look at classic romantic comedies from the nineties. The duo analyzes and ranks the romance dynamics from popular films including Clueless, Never Been Kissed, Pretty Woman, Sleepless in Seattle, and While You Were Sleeping. Jonathan evaluates each couple from worst to best based on real-world relationship quality, safety, and mutual respect, while Alan provides comedic commentary on the cinematic execution of these nostalgic films.#CinemaTherapy#Romcoms#RelationshipTherapist#MovieRanking#NinetiesMovies#Clueless#PrettyWoman#SleeplessInSeattle#WhileYouWereSleeping#MovieAnalysis
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Video Summary
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Hosts Alan Searight and Jonathan Decker analyze 90s romantic comedies through a psychological lens, ranking relationships based on health and stability rather than cinematic tropes. They contrast the \"magic\" of instant attraction with real-world red flags, evaluating whether these classic couples are built on genuine respect or unhealthy power dynamics.
Well, you can't have a dream.
I am majorly, totally, butt-crazy in love with Josh.
Love can feel like magic, but most often those are moments.
The overall feeling is safety and respect.
I need to ask you a question.
A lovely film, you must approach it as fantasy,
because if you look at it through the lens of reality, it's scary as hell.
I remember everything that you say.
It's also stupid.
That's not how the world works, movie!
Wretched.
Hot.
You've never been kissed, and you get to go back to high school and try it all over again,
except you have been kissed.
None of this makes any sense.
It's a lie.
Hello, and welcome to Cinema Therapy.
I am Alan Searight, a professional filmmaker who needs therapy.
I'm joined by my co-host...
Jonathan Decker, Hopeless Romantic.
It's Valentine's.
Yay!
And so, in the spirit of love, we're going to ruthlessly rank.
Oh, okay.
And decide what is good and what is bad.
I'm going to throw some classics at you from our childhood.
90s rom-coms.
Yes!
I was a weird teenage boy in the 90s who loved rom-coms.
I was a normal teenage boy who tolerated rom-coms,
because I could go to them with pretty girls.
Alright.
So, in no particular, but definitely alphabetical order,
we're going to look at...
Clueless.
Ooh.
Never been kissed.
Nice.
Not really.
Pretty Woman.
Okay.
Sleepless in Seattle.
Uh-huh.
And whilst you were sleeping.
Why are you saying it that way?
I don't... Why am I saying what what way?
Where do you get off?
You are going to rank them in terms of relationship quality.
So we'll go worst to best.
Worst to best.
Okay.
I am going to make snide remarks about the quality of the films.
Okay.
Some of them are excellent.
Yeah.
There will be just random commentary and asides.
Just rigmarole.
I've seen the show.
Japes.
Number five.
What's the worst relationship out of the...
Pretty Woman by a wide mile.
It's not even close.
Actually, number four is almost as heinous.
But here we go.
It's very bad.
I'm very sorry.
I'm not happy with Stucky at all for saying that or doing that.
But he is my attorney.
I've known him for ten years.
His attorney called her a whore because Richard Gere called her a whore.
Paranoid.
Well...
Are you my pimp now?
You know, you think you can just...
Came on to her and was really gross.
Mm-hmm.
Can't pass me around to your friends.
I'm not a toy.
I'm speaking to you.
Come back here.
Oh, that's healthy.
I hate to point out the obvious,
but you are, in fact, a hooker.
And you are my employee.
You don't own me.
I decide, okay?
I say who.
I say when.
I say who.
I refuse to spend...
Julia Roberts put a business there.
So good.
That's the end of it.
I said I was sorry I met you.
I'm sorry I ever met you.
That's the end of it.
I'm sorry I ever got into your stupid car.
As if you had so many more appealing options.
Oof.
I've never had anyone make me feel as cheap as you did today.
Somehow I find that very hard to believe.
Man, why write such a mean fight into your romantic comedy?
So he does objectify her and he does use her.
And it's like she likes him because he's rich
and he's slightly nicer to her
than a lot of the people she's had to deal with.
She likes him because this is the last gasp of the 1980s
and he's a rich dude.
I wasn't prepared to answer questions about us.
So you said I'm sorry.
That's good.
It was stupid and cruel.
I didn't mean it.
It's a pretty decent apology.
I don't want you to go.
And he's being vulnerable.
Well, he's being as vulnerable as...
I saw you talking to David Morris.
Richard Gere gets in this.
I didn't like it.
We were just talking.
I saw you talking to another man and I didn't like it.
I'm jealous and possessive.
I didn't like it.
But I'm hot and I'm rich.
And he likes her because she's pretty
and he can save her.
It's very much White Knighting.
I mean, literally, at the end.
Yeah, it's White Knighting the movie.
You hurt me.
Don't do it again.
Okay, so here's why the movie is considered a classic.
In this scene, not as much because it's a conflicting scene.
This is a lovely little gesture.
These two have electric chemistry as actors.
It is absolutely off the charts.
Their chemistry together is dynamite.
And that is really what saves this movie.
It's glossy and flashy and fun.
And it's got good energy.
It saves it as a watchable...
It's very entertaining.
It's very watchable and entertaining.
It is not a good relationship.
No, for the reasons that we enumerated.
My biggest issue with Pretty Woman
is that he mistreats her
time and time again
and it's a story ultimately about
a traumatized woman
who falls in love with a man
who keeps re-traumatizing her.
He's not the initial source of her trauma.
But he keeps it going.
And yes, of course, by the end
he changes and he grows because of her.
I'm not saying there's not beautiful things
about this story.
And it wraps up with a grand romantic gesture.
Which is a grand romantic gesture
which looks really good on film.
But in real life...
It's the little things that lead to...
Love is a commitment
not an action.
Yeah.
Oh boy, some of these couples
could have really used some help
maybe from a couples therapist.
For sure, and that's where BetterHelp could have helped them.
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Like it helped me and my dog.
I have a dog therapist.
Very unhealthy relationship, but at least it's entertaining.
Which I can't say for what I suspect
is number four.
Never been kissed.
This relationship is gross and the movie's bad.
I also have problems with the lead actress
which we'll probably discuss a little bit.
But let's watch some clippy clips.
So she's an undercover reporter posing
as a teenager and her male
teacher has feelings for her.
What did he say?
Real great.
Thank you.
He sees her alone on the Ferris wheel and he's like
I'm gonna go sit next to this teenage girl.
Which she's not, but he doesn't know that.
He doesn't know that.
And she knows he doesn't know that
and she's cool with him flirting with her.
Well, I'll tell you something here.
I hope this doesn't undermine
my position as an authority figure, but
I'm a little afraid of heights.
You're afraid of the Ferris wheel.
Well, actually it's the
plunging head first into the crowd part
that kind of gets me.
Well, I bet if you had your Gordie Howe helmet on
you'd feel better.
Hey, you remember that story?
I remember everything that you say.
In your classroom.
Yeah!
Mr. Colston rocks my world!
That's accurate.
You know, I'd like to tell you that we all grow out of it.
It's alive.
Some of us will always be rattling cages.
Why do you do that?
I don't know.
Speak for old men, please.
You know what's scary is that when you get older
it just gets more confusing.
You know, Laura, my girlfriend you met at the club?
You know what?
I shouldn't be talking about this stuff with you.
I'm sorry. I shouldn't open up about my love life to you.
It's nice to have someone to talk to.
Yeah, same here.
Ah!
The ick of the scene!
Well, all I can tell you is that when you're my age
guys will be lined up around the block for you.
Ah!
You have to say that because you're my teacher.
Wait, wait, wait.
Actually, I shouldn't say that
because I'm your teacher.
Yes!
To the movie's credit, Michael Vartan is playing
Oh, I'm in deep trouble here.
He is playing it that way.
This is the police song
Don't Stand So Close To Me
as a romantic comedy.
Yay!
That's wonderful.
The real issue is the movie's trying to sell this
well, they've got this irresistible
draw to one another and they're destined to be together
and we just need to clear up this misunderstanding.
The real issue is
Drew Barrymore has the
acting talent of a foot.
Oh my gosh.
Strongly disagree, but let's hear it.
She is not a good actor.
She's a foot model actor?
I don't know. I don't know if her feet are pretty.
The thing is, she's not good.
I think she's charming. I've always liked her, but I do see where you're coming from.
I don't care for her personality
and she can't act well.
It's wretched.
I used to feel really bad about it
because I was sure she was a lovely person
and then she scabbed on the writers during the writer's strike
and now I'm like, nah, I don't care, you're a bad person.
You're a bad person who's a bad actor.
The end.
Back to the film.
I also don't think it's a good film.
I was watching and I'm like, I'm not laughing a lot
I'm not feeling a lot of whimsy
the characters are all falling flat for me
but yeah, the biggest thing is
later at the prom, they're dancing together
he sees her and he asks her to dance
because she's about to graduate
and he's asking her about college
and she says, I have something I want to tell you
because she wants to come clean
that she's actually a reporter in her 20s
and he looks at her all misty-eyed
and he says, there's something I want to tell you too
and I'm just, no.
It's just gross.
And then the whole scene at the end
on the pitcher's mound
also not a euphemism
Stupid.
Well, no, it's manipulative.
It's also stupid.
From a script and logistical perspective
she wrote a column in one of two major papers
in a city
and just expects everyone in the world
to have read it
and he's going to show up
That's not how the world works, movie!
Well, it was the 90s.
You had to get creative.
You couldn't exactly send a text.
Mail it to him.
Yeah, not a fan.
John O, what is this movie called?
Never Been Kissed.
Is it ever addressed in the movie
whether or not Drew Barrymore
has actually been f***ing kissed?
I don't think so.
It is, and she has.
The movie is called Never Been Kissed.
The marketing was, a girl who's never been kissed
gets her second chance in high school
and she has been kissed.
She says in a line of dialogue
Well, it's not like I've never been kissed.
Just never really kissed.
What the f***?
What the f*** are you doing?
I hate everyone
who marketed this movie.
The people who wrote it.
You suck. I am sorry.
I do not usually come down on movies.
Everyone tries.
Everyone tries really hard.
Everyone poured their heart and souls
into almost all the movies that got made.
But what the f*** are you doing?
Do not sell me a lie.
Don't call it Never Been Kissed.
Or don't put that line of dialogue in.
Or, even crazier,
make it really about a girl
who is so desperate
for all of this male attention
because she literally has never had
physical affection before.
Do that! That's more compelling.
And then also don't cast Drew Barrymore.
Well, gentle viewer,
Happy Valentine's Day.
I mean, that really got out of hand fast.
This one's going to hurt a little bit, folks.
Sleepless in Seattle
is a lovely film
with wonderful performances
and you must approach it as fantasy
because if you look at it through the lens of reality
it's scary as hell.
So she hears him on the radio,
falls in love with his voice
and feels compassion for his story.
Doesn't actually fall in love with his voice,
let me be clear.
No, she falls in infatuation. Kind of.
Stalks him online,
which was hard to do in 1993, but she manages.
And then she goes to Seattle.
And then in IRL, yeah.
Yeah, and peeks around corners at him.
Also, this is the first time they've met.
Yes.
They've locked eyes twice when she was stalking him.
And where is this at
in the run time of the movie?
This right here is at the very end of the movie.
It's the last scene.
And look, this is charming. This is charming as hell.
Well, the actors really sell it.
Yeah, Meg Ryan and Tom Hanks
are really good at this.
And that kid's great. He's super cute.
Does a good job.
It's you. It's me.
I saw you in the street.
Are you Annie?
Yes.
You wrote the letter.
You're Annie?
Saying I want to give up my life for you
because I heard you on a radio show.
I'm Jonah. This is my dad.
His name's Sam. Hi, Jonah.
She's currently, what,
engaged to worst Bill Pullman,
which is still better than most people.
But not better than Tom Hanks.
No, but she broke it off with him.
She did break it off.
Hello, Howard.
Listen,
immediate infatuation with 90s Meg Ryan
is the appropriate response.
Oh, yes. Absolutely correct.
We better go.
But the movie is saying this is love
and they're going to go the distance
because they zinged.
It's like Hotel Transylvania.
Shall we?
Okay, for those of you who are mad
that we're saying what we're saying,
we've got some really good things
to say about the film and the movie.
I really enjoy this movie.
I just don't enjoy the relationship.
There's problems.
Yeah, there is.
The thing I love most?
Those two.
All the needle drops are so good.
This is one of the greatest soundtracks ever.
Yeah, Nora Ephron knew how to do this.
I mean, the needle drops in
You've Got Mail are maybe even better.
And here's a hot take.
You've Got Mail is better than this.
I agree.
Here's an even hotter take.
Joe vs. The Volcano is better than them all.
Oh, that's not a hot take.
That is just God's truth.
Put that in a stone and bring it down from the mountain.
Joe vs. The Volcano is the goat
of these two together.
The issue, as we were saying,
is she doesn't know him.
She hasn't taken time to see if
who she thinks he is matches up
with her mental image of him.
She's rushed into commitment.
At the end, they're holding hands
and they're like, let's go.
And then they're looking at each other like, wow.
The magic. I feel the magic.
Love can feel like magic,
but most often
those are moments.
The overall feeling is safety and respect.
That's love.
And there's no way for them to establish.
He knows this woman, Annie,
wrote them from across the country saying,
hey, I listen to you on the radio.
This is one of hundreds of letters he received, by the way.
But basically it's, can I be the new mom?
That's basically the letter.
And the whole time she's saying, is this crazy?
I've got Bill Pullman.
And again, worst Bill Pullman is still best.
It's Bill Pullman.
Men find me attractive.
And he's so good to her.
And there's a line in the movie that I really like.
Walter, I don't deserve you.
Nah, I wouldn't put it that way.
But, okay.
Yes, it's very good.
Because she is leaving
what I guess to her is a safe and boring
relationship, flew across the country
and did like George McFly.
Oh yeah, like full Peeping Tom
stocking stuff.
We, the audience,
know that they are perfect for each other.
Because we've been spending all this time with them.
And we see that they match up on all these things.
There's a bunch of stuff that we,
as the audience, know where they're compatible.
And they have no clue.
They have no idea
that any of this is going to work.
This could, could
turn into a great relationship.
What we see in the movie
is not that.
No, it's a grand romantic gesture.
Meet me at the top of the Empire State Building to see if our love is real.
What love? He doesn't even know what you look like.
But I think the movie's great.
I do think it's a really fun movie.
But at the end, I would love to see them see each other.
Feel an instant spark in them.
Say like, you want to get a coffee?
Should Megan and I write that movie?
Should we write the rom-com where they don't meet until the very end but it actually works?
Do it.
If there's anything that goes together even better than Tom Hanks
or Meg Ryan, it's peanut butter
chocolate.
You can get this popcorn along with the other.
You're so angry.
No, I'm excited.
Can you believe this goodness?
I can't believe it.
Yeah, you can get our popcorn at our store.
It's got our faces and not our flavors.
Ew, why would you say that?
Now we get on to
Okay, this is my favorite film on the list
while you were sleeping.
Oh, because you could have gone either way on either one of those.
We've gone from worst Bill Pullman
to best Bill Pullman.
This is best Bill Pullman.
So charming.
We are gathered here today to join
I object.
I didn't get to that
part yet.
I would have to object to
what about you?
I'm thinking.
What the hell is going on?
I am in love
with your son.
I know.
Not that one.
Jack, what the hell
did you do?
He didn't do anything.
It was me.
It was all me.
Elsie, how you doing? You doing okay?
The supporting cast
is so great.
Do you remember that day at the hospital?
Of course you remember that day at the hospital.
There was a little mix up.
I saw Peter get pushed
onto the tracks and I saved his life.
But when I got
to the hospital, they wouldn't let me see him.
So someone
told the doctor
that I was his fiancee
only
it's not true.
She's been saying it has been.
I was never engaged to Peter.
For days or weeks at this point.
Why didn't you say something?
We never even met until that day on the tracks.
It was just when we were in the hospital room
everything happened so fast
and I couldn't tell you the truth
and then I didn't want to tell you
the truth because
the truth was that
I fell in love with you.
You fell in love with me?
No, yes
all of you.
I went from being all alone
to being a fiancee
a daughter
a granddaughter
a sister
and a friend.
I might have saved your life on the tracks that day
but you know what? You really saved mine.
You allowed me to be a part of your family
and I haven't had that in a really
long time.
And I just didn't want to let go of that.
Somewhat schmaltzy writing
saved by great acting.
Turns out this Sandy Bullock is going to have a career
I think.
I'm very sorry.
Oh and I'm very sorry
about your carpet.
What about my carpet?
Peter Callahan is engaged to me.
I object to this wedding.
Get in line.
So while you were sleeping
Romantic comedies generally speaking
need some sort of gimmick.
What's the catch? Oh it's this because this
is happening. Yeah some sort of out there
plot. You know like one of my favorite
ones. Like you've never been
kissed and you get to go back to high school
and try it all over again except you have been kissed.
None of this makes any sense. It's a lie.
Okay. Anyway
like that. Yes like that
some sort of gimmick.
And on the face of it
this is a movie about a woman who
lies to all these people the entire
time and in a less
skillfully written film
she would be an unethical person.
It gets awfully close. There's a couple of times
where it almost bumps me like
this isn't plausible but they manage
to just barely save it with like
script band-aids and really good acting.
Well and so like she wasn't the one
who said I'm the fiance but the family was so
excited and then it was like
grandma can't take any more bad news or aunt
whoever can't take any more bad news. They keep stacking
all these things up. If you tell the truth people could die.
Yeah. They keep stacking all these
things up and she already has such bad
social anxiety that it's like
I kinda buy it. But what I really
love about the romance in this film
is that she falls in love
with Bill Pullman as you do. Of course.
But they maintain their integrity
throughout. Right.
Circumstantially stuff keeps bringing them together
when they're trying to keep their distance.
Right. Because they feel this pull
and it's like for him it's wrong.
This is my brother's fiance. Yeah.
And for her she's like I'm already
in deep enough. Right. And so
a lot of films try to sell the
but there's this irresistible pull
that they have towards one another. Consequences
be damned. And instead of that
it's like there's this irresistible pull they have
towards each other but they're both mindful.
But they keep pushing against it. Yeah.
And they're mindful of the consequences and the other
people in their life that they care about. Yes.
And I also love that she
falls in love with Jack but she
falls in love with the entire family.
It's beautiful. They don't
even get together until
it's all cleared up. Right. My only issue
as far as like real
life is when they get
together it's when he gives her
a ring. Yeah that's a little
dismaying. He goes instead of hey my brother's
awake. You guys aren't together. Do you
want to go get a bite? Right.
Right. Instead he's just like let's get
married. Let's get married immediately.
And again I don't
care because I'm swept up in it and I love
the feeling of it. But this is one of the reasons
we go to movies to escape reality.
So just like James Bond can
literally outrun machine gun fire
I'm not going to try that in real life.
No. You don't jump
straight to engagement but I
love this movie. This is my
favorite of the movies. So number one I would
put the relationship in clueless and no
one was more surprised than me. I'd never
seen this film. I wrote it off as
stupid 90's teen movie
which 90's teen movie I didn't even like
in the 90's when I was a teen. I never cared
for the genre. So I never saw this
and I thought
it was delightful. It's great. It's such a good
movie. What does she want with
Josh anyway? He dresses
funny. He listens to complaint
rock. He's not even cute
in a conventional way.
I mean he's just like this
slug who hangs around the house all the
time.
He's just Paul Rudd all the time.
He's just adorable. He's
such a dork.
Wait a second. What am I stressing about?
This is like
Josh.
Okay. Okay.
So he's kind of a Baldwin.
What would he want with Ty?
She could make him happy.
Josh needs someone with imagination.
Someone to take care of him.
Someone to laugh at his jokes.
In case he ever makes any.
Then suddenly...
Oh my god. I love
Josh.
I am majorly, totally
butt crazy in love with Josh.
But now I don't
know how to act around him.
I mean ordinarily I'd strut around him
in my cutest little outfits and send myself
flowers and candy but
I couldn't do that stuff with Josh.
What's with you?
You're eating plain shredded wheat.
You haven't made me watch the real world.
I care about the news.
Since when?
Since now.
You look confused.
I thought they declared peace in the Middle East.
Bosnia is not
in the Middle East.
That's the joke.
What I really like about her relationship
with Josh who is her
former step brother.
Why I put this relationship
at the top is at least on her end
he inspires her to be a better person
just by being him.
We did an episode on Jane Austen's Emma
recently and having watched that movie
I now realize how closely this
follows. All the story beats are
Emma. But it's about
somebody who becomes a better person
just from the influence of a person she's
falling in love with. And it's not
about changing for the other person
it's about growing. There's
fundamentally changing who you are
and growing into a version of you that was always
in there. And I think that's really
beautiful and healthy and also
Paul Rudd. You can throw
Bill Pullman at me and I'll just counter with Paul Rudd
and we can do that all day. 60% of the
time it works
every time. The exception I would make here
I do think Clueless is a more entertaining
film than While You Were Sleeping.
That's up to taste pretty much at this point.
They're both excellent films.
I would probably
rank While You Were Sleeping as a
slightly healthier relationship just because
there's not the
ex-step-brother
slight ick factor
there and also the potential
statutory factor of
he's 18 or 19 she's
16. It's not
the worst thing in the world but it's
They just gotta keep their hands above the equator
for a few years.
He's out of line
but he's right. Now I have concerns
of an entirely other nature
but no the real concern
though is he makes her better
she doesn't seem to have a
heck of a lot of influence on him.
Maybe a little bit. She gets him to
loosen up and be a little more fun maybe.
We see why she falls in love with him
but why he falls in love with her is just like
she's attractive.
Yeah I can see that because in While You Were Sleeping you
really get what they like
and respect about each other.
I might have to rethink this whole damn
thing. Happy Valentine's Day.
Hey listen it's about feelings
and you felt
your feelings are not wrong.
I mean they are but
I've just proved it logically.
Thanks Spock!
What did you think of my rankings
of these couples? Would you stagger them differently?
And what is a healthier relationship
While You Were Sleeping or Clueless?
And what's a better movie While You Were Sleeping
or Clueless? And do you strongly disagree
with anything we said? Why do you hate my take
on Never Been Kissed? And if you're Drew Barrymore's
PR team we're just going to block you.
Baramites! Unite!
So until next time.
Then it happened.
I fell in love with you.
You fell in love with me?
All of you.
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Billy Bumbler
Billy Bumbler 19
That is an amazing name.
Steven Also Clever
Yep
That's a new one. Shante Taylor
And Sylvia Salmon Burns
It's hyphenated.
It is hyphenated. And it's not
like the fish. She didn't just like
cook a salmon and burn it. We love you all.
Thanks Sylvia.