Operation: Teardrops
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As my first choice, a movie both me, Kyle, and Mike are interested in seeing. I've only heard good things from the people who have watched it. A plus! It's also fairly depressing!
The Results:
Well, I cried watching this, but Mike did not. It is, however, a movie both of us absolutely love!
The Results:
Well, I cried watching this, but Mike did not. It is, however, a movie both of us absolutely love!

Dierdre's rating:

Brothers (2009)
Now, Mike's your average guy, so romances might not do the trick for him. Next up is Brothers, somewhat of a war film, with his favorite actress, Natalie Portman.
I mean, MIA soldiers, "unfaithful" wives--this movie might do it!
The Results:
Pending.
I mean, MIA soldiers, "unfaithful" wives--this movie might do it!
The Results:
Pending.

Dierdre's rating:

The Notebook (2004)
Don't tell anyone, but I haven't actually seen the Notebook! I heard, however, that it was just a sob-fest. Maybe a story of undying love will do it for him. If not, Kyle and I will probably be bawling our eyes out. :D
The Results:
He adamantly refused to watch this movie on account of he'd already seen it and thought it was God awful. It clearly didn't make him cry.
The Results:
He adamantly refused to watch this movie on account of he'd already seen it and thought it was God awful. It clearly didn't make him cry.

Dierdre's rating:

Oh goodness, the first time I saw this, I was literally curled up in a ball crying for hours. I don't even remember why, but it just made me want to eat Godiva all day.
I believe Kyle had a similar experience.
Mike? I'm not sure if he's ever watched a romance/drama.
The Results:
Pending, but he seems uninterested.
I believe Kyle had a similar experience.
Mike? I'm not sure if he's ever watched a romance/drama.
The Results:
Pending, but he seems uninterested.

Dierdre's rating:

Requiem for a Dream (2000)
A movie about drug addicts--while not going to touch my friends personally, maybe it'll be depressing enough to move us.
I want to watch this movie so badly, and I have high hopes for this movie.
The Results:
Pending.
I want to watch this movie so badly, and I have high hopes for this movie.
The Results:
Pending.

Yeah, one of my high school Asian friends had us all sit down at a party to watch this movie about Richard Gere and a dog. I thought it was ridiculous up until in a room full of other kids, we're all audibly sobbing and passing around the tissue box.
The Results:
Pending.

The Results:
Pending.

Dierdre's rating:

Okay, Mike and I tried to sit down and watch this once, but it didn't work out the way I planned and we only saw 10 minutes. Maybe if we really try next time we can get through it.
It seems pretty sad, but this is at the bottom of my list for now. It's just not something I can imagine us sobbing to (with all the naked ladies running around).
The Results:
We've thrown this one out. It has too many naked ladies too be heartfelt.
It seems pretty sad, but this is at the bottom of my list for now. It's just not something I can imagine us sobbing to (with all the naked ladies running around).
The Results:
We've thrown this one out. It has too many naked ladies too be heartfelt.

Dierdre's rating:

Moulin Rouge! (2001)
Ugh! That end scene is just so sad!
This list seems more like an excuse for Kyle and me to watch our favorite movies together than anything.
Oh well. Maybe we'll make Mike cry from the pain of watching romances.
The Results:
Watched. Only Kyle cried.
This list seems more like an excuse for Kyle and me to watch our favorite movies together than anything.
Oh well. Maybe we'll make Mike cry from the pain of watching romances.
The Results:
Watched. Only Kyle cried.

Dierdre's rating:

Another movie probably all three of us want to see. Even if it's not a movie to cry to, it's depressing enough that just maybe it'll work.
The Results:
He's already seen it. It didn't make him cry.
The Results:
He's already seen it. It didn't make him cry.

I think I'm the only one that wants to watch this movie, but I'm putting it on this list anyways. Although, I do need to read the book first. :\
The Results:
Pending.

The Results:
Pending.

Dierdre's rating:

The Last Samurai (2003)
It's a long shot, but I'm trying to switch up the genres a bit so we're not always watching romances.
The Results:
He'd already seen it. It didn't make him cry, but he liked it.

The Results:
He'd already seen it. It didn't make him cry, but he liked it.

The Pianist (2002)
No one wants to watch this movie with me! D:
I've had it checked out of the library several times but it seems every time I do, other plans come up. So, I'm going to force Mike and Kyle to watch it under the ruse that it will make Mike cry.
This idea is foolproof.
The Results:
Pending.
I've had it checked out of the library several times but it seems every time I do, other plans come up. So, I'm going to force Mike and Kyle to watch it under the ruse that it will make Mike cry.
This idea is foolproof.
The Results:
Pending.

Dierdre's rating:

P.S. I Love You (2007)
Another romance, but I can't help it. It's hard to think of movies to cry to and not have the cliche Romance novel-types pop into your head.
There seem to be a ton of mixed reviews on this one. Most of the girls I know either loved it or hated it, and there's no in between.
The Results:
Pending. He still doesn't like it.
There seem to be a ton of mixed reviews on this one. Most of the girls I know either loved it or hated it, and there's no in between.
The Results:
Pending. He still doesn't like it.

Dierdre's rating:

The Green Mile (1999)
Not the first movie to come to mind while making this list, this Dark Horse has great reviews and is apparently quite depressing, even with the bland title.
It won't be Kyle's favorite movie on this list, that's for sure, but this operation is all about Mike.
The Results:
Pending, but he thinks he's seen it and it didn't make him cry.
It won't be Kyle's favorite movie on this list, that's for sure, but this operation is all about Mike.
The Results:
Pending, but he thinks he's seen it and it didn't make him cry.

I Am Sam (2002)
This movie just sounds sad! I almost teared up reading the description. It's going on this list whether Kyle likes it or not. The characters are so dynamic, I think I'll enjoy this movie.
The Results:
Pending.
The Results:
Pending.

Grave of the Fireflies (1988)
I don't usually associate animated films with sadness, but after Toy Story 3, I guess anything's possible.
The overall consensus of this movie is that it is "GODDAMMIT THE MOST DEPRESSING MOVIE I THINK I MIGHT DIE FROM HEARTBREAK SOMEONE JUST STOP IT PLEASE I THINK I'M GOING TO CRAWL INTO A HOLE NOW AND NOT COME OUT SOMEONE SHOOT ME AND PUT ME OUT OF MY MISERY I WON'T EVER KNOW THE COMFORT OF HAPPINESS AGAIN."
The Results:
Pending.

The overall consensus of this movie is that it is "GODDAMMIT THE MOST DEPRESSING MOVIE I THINK I MIGHT DIE FROM HEARTBREAK SOMEONE JUST STOP IT PLEASE I THINK I'M GOING TO CRAWL INTO A HOLE NOW AND NOT COME OUT SOMEONE SHOOT ME AND PUT ME OUT OF MY MISERY I WON'T EVER KNOW THE COMFORT OF HAPPINESS AGAIN."
The Results:
Pending.

Philadelphia (1993)
My dad tried to get me to watch this movie, I feel kind of bad for blowing him off. I thought it'd be a boring film.
It seems very sad and moving, maybe I'll give it a shot soon and convince the boys to watch it with me.
The Results:
Pending.
It seems very sad and moving, maybe I'll give it a shot soon and convince the boys to watch it with me.
The Results:
Pending.

Dancer in the Dark (2000)
I haven't heard much about this movie, but after seeing it on a couple of "SADDEST MOVIES" lists, I thought it deserved a place here.
Any movie with Catherine Deneuve is good in my book.
The Results:
Pending.
Any movie with Catherine Deneuve is good in my book.
The Results:
Pending.

Sophie's Choice (1982)
Movies about the Holocaust always make me want to bawl my eyes out. I bet this one will be no exception. This, and Dancer in the Dark, will be a hard one to convince Mike to watch, but it's worth a shot.
The Results:
Pending.
The Results:
Pending.

East of Eden (1955)
An older film, but that won't be a problem with Mike and Kyle. This seems to be a very interesting film and I'll hopefully get the chance to watch it regardless of whether or not it makes Mike cry.
Anyways! It's a John Steinbeck story! If that doesn't make you feel like dying, nothing will.
The Results:
Pending.

Anyways! It's a John Steinbeck story! If that doesn't make you feel like dying, nothing will.
The Results:
Pending.

La Vie en Rose (2007)
Kyle made me put this one on, and I've already seen it and loved it. I'm pretty sure it's not the kind of movie Mike would like, but I guess it's worth a re-watching, especially with Marion Cotillard involved.
The Results:
Pending.

The Results:
Pending.

Dierdre's rating:

Marley & Me (2008)
Don't tell anyone but Mike's the one who wanted to watch this movie. I was somewhat interested in renting it, simply because I heard some people cried during it, but it ended up in my pile after some light prodding by him.
The Results:
Well, I teared up a bit, but it gets somewhat sad and I cry at everything. Mike was stoic, but he liked the movie much more than I did, saying it was "real emotionally." So, simply, no waterworks this time.

The Results:
Well, I teared up a bit, but it gets somewhat sad and I cry at everything. Mike was stoic, but he liked the movie much more than I did, saying it was "real emotionally." So, simply, no waterworks this time.

Dierdre's rating:

This is a list of movies my gay best friend, Kyle, and I are using in an attempt to make my boyfriend (now ex), Mike, cry.
According to the both of them, the boy hasn't cried in years. He's afraid he's lost the ability. So, we've concocted a plan. We shall make him watch some of the most depressing movies--as many as possible in one weekend.
Avoiding ones he's already seen, here's what I have.
According to the both of them, the boy hasn't cried in years. He's afraid he's lost the ability. So, we've concocted a plan. We shall make him watch some of the most depressing movies--as many as possible in one weekend.
Avoiding ones he's already seen, here's what I have.
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