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20 Of My Favorite “Happy Classic” Movies To Help You Escape (Plus My #1 Movie of All-Time)

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We all deserve an escape right now with no shame in our Quarantine Game. But then again I’ve never been one to feel guilty about any of my pleasures and happily promote the genius of Outlander and Gillian Flynn books despite knowing that these will never be critically acclaimed. I actually wrote this post 3 years ago but never posted it because why would I publish a ‘my favorite all-time movies’ on a design blog? I’m not a film critic, in fact, quite the opposite. I mostly like entertaining rom-coms and coming of age movies. But these days I need a guaranteed good escape (we all do) so turning to the “happy classics”, as I call them, seems necessary. You’ve probably seen all these movies – they are the movies that when on a plane you can’t NOT watch. The characters feel like friends. You tell yourself you’ll just press play for a second then you find an hour and a half of JOY has passed as you’ve watched Kate Hudson and Matthew Maconahay flirt. So, here it is. My favorite “Happy Classic” movies (with some 2020 updates).

20. Someone Great

This one is more friend love than and dealing with a breakup than anything, but the LOVE is there – it’s just less rom-com and more about female friendship (which is, honestly, equally important). 

19. How To Lose a Guy in 10 Days:

The first time you watch this you’ll be embarrassed by how much you like it. The plot is so cliche and shallow, but they both sell it, you believe in them, and there are some strangely hilarious moments having to do with a tiny yappy dog. It’s become a classic in my book.

18. Always Be My Maybe

Finally a new one from 2019 that is becoming a go-to in the background. Great acting and sweet story. Just talking about it makes me excited to watch it again. 

17. Bad Moms

This is another go-to plane movie while I write posts, not that I’ll be on a plane anytime soon. It seems highly appropriate right now as a lot of us moms might be feeling extra bad (or good?) these days. Speaking of Kristen, a funny post I saw was a mom saying “While homeschooling we need more structure to our day, so tomorrow we are watching Frozen 1 BEFORE Frozen 2”.

16. The Proposal:

It’s practically perfect. Sandra and Ryan are so good, Betty White (and all the other silly character actors) entertain thoroughly and it has enough heart to really root for them the whole way.

15.  Devil Wears Prada:

I worked in the magazine industry in New York in my 20s so this certainly speaks to me, but even if I didn’t I’m sure I would love it. Anne and Meryl kill it, and it has heart, glamour and some hunky love.

14. Set It Up

 I watched this twice in the same week. The two leads have such good chemistry and all the acting is great. I, again, apparently love the “hustling in the magazine industry as a 20 something” genre, but maybe we all secretly do? 

13. Bridesmaids

I can’t. It’s too funny. And has heart with the girl friendship situation. I know you have all seen it, but just watch it again. You’ll be so happy you did.

12. The First Time

YOU GUYS. No one has seen this movie and it’s VERY VERY VERY good, cute and a great one if you are with a partner to watch. It’s a rom-com meets coming of age and those are my two favorite movie genres.

11.  The Notebook

I used to give myself a “1 Notebook a year” allowance for fear that I would watch it too many times and it would lose its specialness (besides the more you watch it, the more flaws you see). I swear I should be a Hollywood trend actor predictor. I KNOW when a male actor is going to hit big time from their first film. I was a fan of his before watching this, too, but after this, I was like THIS GUY WILL SWEEP THE WORLD. Of course, he turned slightly into a D-bag and he’s a bit oversaturated but this movie is still uncomparable on the romance/love-ometer (which is the only meter I care about).

10. Ten Things I Hate About You

’90s angst meets Shakespeare. It’s not particularily amazing but I love when its on TBS. Plus …. Heath.

9. A Lot Like Love

Amanda PEET, Ashton KUTCHER – Visuel de l’Affiche Américaine en Couleur – Color Key Art

How is this not a more popular classic? I LOVE LOVE LOVE LOVE this movie. They have such great chemistry and it’s coming of age in a really fun 2000s kind of way. If you haven’t seen it, please rent it.

8. Definitely, Maybe

He can do no wrong, and while many people think this tale of a movie is cheesy, I for one love watching it over and over. Definitely. Not maybe.

7. Sweet Home Alabama

Pretty much the exact same plot as The Notebook (have you noticed that?) but I’m a huge Josh Lucas fan and I think this movie is entertaining from New York to Alabama.

6. Parent Trap

I was a Lindsey Lohan fan for a long time (and still am, despite her terrible childhood led by unskilled albeit surely loving parents). I love this movie. Not sure why. But it makes me happy.

5. Crazy Stupid Love

YES. UGH. All-star cast, about love and relationships. Emma and Ryan’s love + Steve’s hilariously depressing character makes me smile.

4. The Girl Next Door

This is lesser-known but it is GOOOOOOOD. It’s one of the few romantic comedies that Brian loves as much as I do. This one is about a girl know moves next door to a normal teenage boy, and she is a porn star. It’s not what you think. It’s full of heart and romance.

3. Dangerous Beauty

You are welcome, female America. You are all thinking “what is this movie that I’ve never heard of??” GAH. It’s so good!!!!! I would kill to watch it right now. It’s a sleeper hit (no pun intended) about a courtesan and it is romantic as HELL. It sweeps you away, puts you in the mood and yet makes you feel empowered. WATCH IT.

2. Mean Girls

See. I told you I was a Lindsey fan. And Rachel. And Tina Fey. It’s an obvious classic.

1. Dirty Dancing

That’s right. Dirty Dancing is my #1 movie OF ALL TIME and there is no shame in my Patrick Swayze loving game. And you know what? After I made Brian watch it recently it’s also one is HIS favorite movies. The acting, the production design, the music, the romance – EVERYTHING is so good. And Patrick Swayze truly was a national treasure.

But those are just my “can’t not watch” movies and while I may be able to sneak some time to watch them the next few weeks, even if it’s just on in the background while I write at night, I’d LOVE some new recommendations (or ones that I’ve missed). For instance my team already pointed out that I haven’t seen To All the Boys I’ve Loved Before and I’m so excited to stream it on my laptop while I organize SOMETHING, JUST ANYTHING this weekend. But it’s also been a couple of years since The Notebook so that might be on my agenda as well. Also please don’t forget any “switching bodies’ movies i.e. 13 going on 30, 17 again, The Change Up, etc. Also, I can’t believe I didn’t put Good Will Hunting up there, not because it’s a good rom-com, but Matt and Ben’s friendship makes me really happy. Ok gotta stop, now you please start – what are your “Happy Classics” for all of our no guilt escaping right now???

Fin Mark

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I also want to say that I LOVE Someone Great because I finally felt like I saw women around my age portrayed how a lot of us actually are! Perfectly imperfect. Plus Gina is such a treasure and if you haven’t seen Jane The Virgin I suggest you do that right now (FYI it may take a minute to get into but it’s SO worth it)

Sonja

Yes. Yes to all of that. Gina is a national treasure.
Fun fact! My family plays a game called National Treasure and it’s based entirely around who I will or will not personally declare a National Treasure. Basically family members pick someone famous and I state my declaration of yes or no and they try to anticipate my answer. I will happily and passionately defend my answers.
Anyway, give the game a go. And I feel very seen by this list. I have to balance my binging of all things Crooked Media somehow, someway.

She totally is and that sounds so fun!!

EP

Yes! Jane the Virgin is one of the best shows and so underrated. It’s been over for a while and I find myself wishing still it was on TV.

So many of the movies you listed are my long time faves (10 things, Notebook, Crazy Stupid Love, Parent trap!) A movie I would recommend is Chocolat. Juliette Binoche, Johnny Depp, and Judi Dench are so good.

Thanks for these recommendations, Emily, I’m in need of some solid movies to watch during quarantine.

Vicki Williams

YESSSS! On Chocolat!

Meredith

Yes! OMG, I just watched the final episode of Jane the Virgin last night, and it was so perfect. I cried. Magda with her hook and peg leg–that looks like a table leg. I can’t. The show is so funny and dramatic and romantic.

I’m excited for you to watch To All The Boys I’ve Loved Before! I went on a binge of Netflix’s Summer of Romance but of those movies, that one and Set It Up are definitely the best ones. The sequel is actually good too!

What I really came here to say was, of course, how could you possibly say “It’s not particularily amazing” as applied to 10 Things I Hate About You????? I feel confident this is the statement published on this site that I will always and forever disagree with the MOST, lol. Might be time for a rewatch there too, seriously such good high school dynamics!

You might also enjoy reading the column in the AV Club discussing romcoms, it’s really thoughtful and fun to read (though I believe she might be down on How to Lose A Guy in 10 Days so maybe skip that column).

Completely agree about 10 Things I Hate About You, it is one of my all time favorites!

While I love Emily, I also HIGHLY disagree with her “10 Things I Hate About You” statement. It’s easily in my top 3 of all time. I think it’s 90s masterpiece:)

I can third that disagreement on 10 Things I Hate About You as it’s one of my favorite RomComs of all time, but most of the movies on this list are also my go-to’s, so you definitely can’t go wrong here 🙂 also I recommend Say Anything if you haven’t seen it!

Terri

I love a lot of these and I am definitely going to check out the ones you mentioned that I haven’t seen. I love French Kiss with Meg Ryan. And what about Family Man with Nicholas Cage and Tea Leoni? My Cousin Vinny I think is hilarious but it’s more of a comedy, not a rom-com. My Best Friend’s Wedding…there are so many!

AH!!! My Best Friend’s Wedding is so gooooood. Love Julia!

Jenn

“Seeking a friend for the end of the world” is strange and sweet and kind of appropriate for the world right now

“The Philadelphia Story” is a perfect classic: Hepburn, Grant and Stewart. So good

Jenn

Forgot:
Auntie Mame

Great movie
Fabulous interiors

Colin

That gives me an idea for the EHD team to write a post about; ranking and get the looks for great movie interiors. Some other great movies with cool interior design in addition to “Auntie Mame” would be “Breakfast at Tiffany’s” (who could forget that custom bathtub couch?) , “An American in Paris” (with the mesmerizing sequence at the beginning where the one room artist’s garret is transformed from bedroom to work space) and “Gigi” (I am seriously envious of Maurice Chevalier’s moody art nouveaux bachelor pad). This would be a great way to combine quarantine mandated movie marathons with decor!

Ooooh i like where your head is at, Colin!! loving the recommendations from you all 🙂

Lacy Ellsworth

I just watched an old favorite called Pillow Talk. The main character actually is an interior designer and her apt is amazing! Plus it has a hilarious design twist. Warning some parts almost seem sexist, it’s the 60s man, but they actually acknowledge themselves.

HH

Yasss! The interiors in Pillow Talk!

Lulu

Please do this!!!!

Rebecca

One of my favorites is “While You Were Sleeping”with Sandra Bullock and Bill Pullman. It has its flaws, but so many funny little moments and charming characters.

Teresa

I love, love, love this movie so much! Also, Joe Jr. always steals the show.

carrie

Yes – Joe Jr. is the best!

y

My family always asks if he was “leaning”, as in “well was he LEANING?”

Siel

Haha I love this! My n°1 in this list is definitely the notebook *swoon*

Erin

Sliding Doors. The first time I saw it, 20 years ago, I thought “well, that was fine but probably not a movie I would watch more than once.” Then I watched it again. And again. Now it is a total go-to. One of the few movies I owned on VHS that I rebought on DVD (and now neither of those media is required of course!)

Such a good one!

Kristyn

If you have Amazon Prime, watch Catastrophe or Fleabag. Not really RomComs in the traditional sense, but definitely about love. Catastrophe is LOL funny. Fleabag season 1 may seem like a slow build and her self destructive ways can be hard to watch at times, but season 2 is a masterpiece.

Betty

Yes to Fleabag and season 2 being a masterpiece! I am so glad I hung in there …
Have to check out Catastrophe now – thanks!

FLEABAG !!! Season 2 absolutely stole my heart, locked it in a box and threw away the key.

Lulu

Catastrophe is excellent and really nails marriage. You will cringe at times.

OMG> YES YES YES to Dirty Dancing! And yes, Patrick Swayze WAS a national treasure. If you like him, you should watch City of Joy! So goooooooooooooooooooooooooooooooooooooood. Not a lot of people know this.
Also, if you love a good movie that is depressing, House of Sand and Fog.
And, if you love an awesome lighthearted movie, Clueless can’t be beat!

Dangerous Beauty……..I know I’ve seen this, but can’t remember what it was about. Now I need to rewatch!

CLUELESS!!! How did this NOT come to mind!?!?

Kristyn

Also – Brooklyn with Saorsie Ronan is a very sweet romantic movie.

Agree! That was a great airplane movie find for me:)

ugh i looove saoirse!! adding this to my list 🙂

Jennifer

Oooh, some new-to-me movies here. Can’t wait to watch them. My favorite rom-coms are Shakespeare in Love and Notting Hill. My favorite all-time movie is Out of Africa. Streep and Redford? C’mon!

O shoot I need to watch Shakespeare in Love stat

Lauren

My favorite feel-good movies are Bridesmaids, Mary Poppins, Paddington, and The Princess Bride…I’m sure there are others I’m forgetting, but those came to mind.

Suzanne

Love The Princess Bride!

ok THANK YOU LAUREN !! i tell everybody to watch Paddington because it is truly such an amazing movie, but nobody ever believes me!

About Time is cute time travel British comedy/romance, The Blind Side, and Sliding Doors (early Gwyneth P.).

About Time is SO CUTE. I always am like, “I definitely won’t cry during this, I know what’s going to happen” and then NAH. TEARS. Every time. SO TENDER.

Ahh thank you for reminding me of About Time! Such a good one:)

About Time is a cute British time travel comedy/romance, The Blind Side (Love Sandra Bullock) and Sliding Doors (early Gwyneth P.).

Amy

+1 for “hustling in the magazine industry as a 20 something” genre. I’ve been racing through an embarrassing amount of Bold Type (a tv show on freeform and hulu). Recommended.

Adding Bold Type to my list, thanks Amy!

THE BOLD TYPE IS SO GOOD !!

Maggie

My favorites are When Harry Met Sally, Sleepless In Seattle, You’ve Got Mail (can you sense a trend?), 500 Days of Summer, and Marry Poppins. And absolutely yes to 10 Things I Hate About You and Dirty Dancing!

Suzanne

When Harry Met Sally is my favorite, too!

Julia

LOVE when Harry met sally but will also echo all Nora ephron everything

hey Maggie! my roommates and I just watched When Harry Met Sally for the first time a few months ago and wowie!! so good

Margaret

My favourite movie of all time is We Bought A Zoo. It’s more heart wrenching than I expected, but such a feel good life is crazy but amazing movie!

Jenna

This is a near flawless list! I can never get enough romcoms. But, I must put in my vote for Bridget Jones Diary (the first one and only the first one). I could never watch that movie enough. There is also a lesser known Hugh Grant and Drew Barrymore movie called Music and Lyrics that is a hidden sleeper as well.

AHHH fully agree! Bridget Jones is one of my favorites.

Arlyn

Bridget Jones +1. And say what you will to shame my, but the third one where she has a baby…seen it at this point maybe 10 times? It’s my “watch on a plane every time I fly” pick. Oh and It’s Complicated. Oh and Somethings Gotta Give…basically anything with Diane Keaton or Meryl Streep.

Suzanne

Both great movies!

Jillian L

Bend it Like Beckham is a forever favorite!! Also, anything Nancy Meyers does because of the set design… 🙂

Bend it Like Beckham, i love!! haven’t seen it in so long, might have to watch soon 🙂

Alexandra Rose

Money Pit with Tom Hanks
Princess Bride
Romy and Michelle’s HS Reunion
Farris Bueller’s Day Off
A League of Their Own
?

Ahhh Princess Bride and Romy and Michelle would both be on my list.

I made Chase watch 10 things I hate about you and he LOVED IT. It’s the best movie to watch right now. Also, how did 27 dresses not make the list? Is anyone else with me?? My sister would definitely back me up on this…

YES MAL. I’ve watched 27 dresses a thousand times. I have the biggest crush on James Marsden

James Marsden !! such a heartthrob that man

Elaine

Great list! I would add Pretty woman,
Plus One on Hulu, My Best Friends Wedding, Along Came Polly, and I totally agree with the Fleabag recommendation.

PLUS ONE! I watched that movie after Em recommended it (I think she watched it on a plane!!!!) and OMG IT’S SO CUTE AND FUN. 10/10 rom com!!!

Lisa

I mean I was gonna recommend To All The Boys I Loved Before but apparently your team is way ahead of me 😉 – I have already rewatched this move an embarrassing amount of times! I also love a good coming of age movie so I would add (in no particular order whatsoever) -Easy A (Emma Stone! hilarious! great (and smart!) story line! the coolest family!), -The Duff (not neccesarilly a ‘quality movie’ but I love her and their chemistry is great (also I will always love a good transformation)) – And I also really really love Enchanted (so so funny, Amy Adams is a treasure, and the soooongs (the only tragedy is that Indina Mendzel is in it and she doesn’t sing – whyyyy??)), – Not a movie, but I really enjoyed the series The Bold Type (about three friends in their 20s who work at a wonderful(ly unrealistic) fashion magazine and its all about female friendships), -I also love Miss Fishers Murder Mysteries (its my comfort food) – I will always love Miss Congeniality (my go to movie when I’m sick), – I also recently watched Ocean’s 8 and really loved it (everybody is great and funny and… Read more »

Lisa

And how could I forget Rent (the musical)?? Literally my most favourite peace of art of all time and the movie version is great!!!

Enchanted is so sweet!

girllll you are speaking my love language right now. Easy A i have easily (ha no pun intended) seen at least 10x. Enchanted is so sweet!! love The Bold Type, TATB, Ocean’s 8 ugh everything you said i full-heartedly agree with !!

Lisa

Another one I shamelessly rewatch again and again is The Holiday – its actually not thaaat great but somehow I love it? I actually like the bits with Kate Blanched and Jack Black, more than the ones with Cameron Diaz and Jude Law, I just really enjoy their chemistry. Since I have the movie pracitically memorised by now I will sometimes just skip the parts of the other couple…*shame face*

Jenn

Oh I love The Holiday…. the relationship between Kate winslet and the neighbor is the best

Patricia

One of my favs, too!! But it’s Kate Winslet, not Blanchett ?

Jude Law had me swooooning in The Holiday

LEGALLY BLONDE IS MISSING. #1 forever and always.

Legally blonde made me want to become a lawyer. Obviously I didn’t but STILL. It’s clearly such an inspiring film

Ryann do we have twin movie tastes??? Are we in love???

Ryann I could totally see you being a kick-ass lawyer! Especially if saving dogs was the goal:)

petition for Ryann to be the next Elle Woods!

Helen

You’ve Got Mail, While You Were Sleeping,

emily

Desperately Seeking Susan!

Jenny

Love the list-so many of my favorites. I would recommend “Love, Rosie” and “Just Friends” (with Ryan Reynolds).

I love Just Friends!

Claudia

I love The First Time! I was so sad when they took it off Netflix!

me too!! I used to have the biggest crush on Dylan O’Brien, so this movie has a special place in my heart

Andrea

You’ve got mail isn’t on this list?? ??? It is the most soothing rom com of all time. Also! Emily, I hope you check out Salmon fishing in the Yemen and subsequently add it to this list. It is very pleasing and palatable.

Erika

Oooh definitely missing Princess Bride (Inconceivable!! that it’s not on here ?), also Clueless and my guilty pleasure that I probably can recite all the lines along with: Center Stage. Zoe Saldana! Real dancers! Impossible costume and hair changes!

shauna

YES TO ALL ESPECIALLY CENTER STAGE!

Jenn

Agree with pretty much every movie mentioned on this list and in the comments, but I HAVE to add the movie What If starring Daniel Radcliffe and Zoe Kazan. These two have such great chemistry and dry humor, I can’t get enough. Also the movie Flipped is super cute and all about first childhood loves. I’ve lost count of how many times I’ve watched it 🙂

ugh Jenn, i loved What If!

Katie

Lloyd Dobler. Forever

amen, Katie !!

j

Return to Me
Minnie…the bright colors…the one-liners…Caroll O’Connor…the Italian Old Men…so good.

Carrie

Definitely – hilarious and I always tear up.

Pallavi

Richard Linklater’s Before Sunrise – Before Sunset – Before Midnight trilogy!! Masterpieces, especially the first one (Before Sunrise). Ethan Hawke and Julie Delpy are incredibly relatable.

N

My all time favorite plane movie is Miss Congeniality. It’s quite sexist upon rewatching, but Sandra Bullock is a National Treasure.

Sandra for President!

Lauren

Emily: if you like Crazy Stupid Love you HAVE to watch Stuck in Love. Greg Kinnear, Jennifer Connely, Lily Collins, and a killer Kristin Bell bit part. Fantastic chemistry across three generational romances. You’ll love it. Like new favorite LOVE IT.

Also, obviously About Time but it’s actually kind of also a cryer.

Betty

All nice movies….here are some international ones.
Once (Irish romance)
Red Dog (Aussie movie – one of the best)
Amour (French – not for the faint)
The Lives of Others (German – life in former East Germany)
A Separation (Iran – marriage trouble)
Life is Beautiful (Italian movie during WWII)
The Postman (Italian romance)
The Intouchables (French – feel good movie about friendship)
The Joy Luck Club (Chinese – relationship between mothers and daughters)

Most are available through Amazon prime or Netflix

thanks for the recs, Betty!! 🙂

HH

Amour and A Separation are so, so good. Not easy movies, but so good.

Y

Can I add Amelie to that list? My 16 yr daughter and I swoon together over everything in that movie.

sally

OMG Once! I met the stars a couple of times through an old job I had and Glen was so lovely. One of the best under the radar films!

Pat

Some of my favorites: P.S. I Love You, Bridget Jones’s Diary, The Holiday, Across The Universe. I could go on……??

Jane

First Wives Club! Another 90s classic that is still really great.

o yes!

Sara

Okay adding some yet unnamed “classics”
Love and Basketball gets me EVERY TIME! Like yeah sports but also, Omar Epps!

Also a real sleeper from my youth, Playing by Hearts. Ultimate late 90s ALL-STAR cast. Jon Stewart plays a love interest, Angelina Jolie, Sean Comedy!

Lexa

I LOVE Playing By Heart! I have not rewatched it in *years* but it may make this weekend’s lineup!

Vicki Williams

Spanglish! Run do not walk to watch this. I rented it from library once and ended up watching it every day for a week! Penelope is so beautiful and Adam Sandler is a good man! It’s a kind of a “take the high road” that you seldom see anymore, which I love! Sorry, no sorry! Soooo good!

Roberta Davis

I liked this, too! Have watched 2-3 times.

Brooke

Funny. I own ONE dvd. I’ve had it for years and yes- it’s my favorite movie too! Dirty dancing for the 40 y/o lady win!

If they is only one, that’s a GREAT one!

Kim

This is such a great list! Also have to add Pride & Prejudice – my all-time favorite (with Keira Knightley). Love Actually is up there too.

I have still not seen Pride & Prejudice (i know. total face slap emoji), but it is on my list!

Roberta Davis

oh! Ya gotta!

V you need to!

I am starting a Quarantine Movie List, so that’s now on it!

Kate

Love Actually – the best!!!

Meghan

Did Ryan Gosling do something I didn’t hear about?! “Only You” is so good. Marisa Tomei and Robert Downey Jr. in Rome! “Something’s Gotta Give” always makes me happy too, and Joss Whedon’s modern-day “Much Ado About Nothing” made my heart soar! To All the Boys is a must watch!

Kate

Such great movies! I’m excited to watch Set It Up soon!!

I recently watched Irreplaceable You on Netflix and loved it. Maybe not a classic, but good. My list also includes Age of Adeline, Return to Me, and While You Were Sleeping. ❤️❤️❤️

Karly

I’m sorry, but how is Moonstruck not on this list?! It’s Cher and Nicolas Cage looking gorgeous, and Olympia Dukakis at her comedic best. There are SO MANY hilarious lines in this movie, not to mention a great makeover scene. Cher is a national treasure.

Also, Return to Me with Minnie Driver and David Duchovny is fantastic.

Roberta Davis

Agree on Moonstruck! And Mermaids was good, too! With Cher.

Alyssa

Hellllooo…Notting Hill!! Kills me. And You’ve Got Mail for cute 90s Meg Ryan.

Notting Hill is so gooooood !!!

Caroline

No thank you. I am female can’t stand chick flicks.

Nataša

My favorite movie is Love, actually. No matter how many times I’ve seen it, there is always a new detail. It makes me feel so good. And then there is this Emma Thompson scene that deserves standing ovations.
I will also second About time recommendation, so nice.
No one mentioned As Good As It Gets.

Kelly

Yes! Love, Actually is so so good. I watch it almost every year. There are some wonderful actors in this movie and Emma Thompson is amazing!

I also love Notting Hill, and The Wedding Singer…my fave Adam Sandler movie. So good!

Roberta Davis

After watching it like 15 times, I finally got the Claudia Schiffer thing!

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