When Harry Dumped Sally

40 Episodes
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By: Tess Menzies, Natasha Vinik

A cynical podcast about love hosted by Tess Menzies and Natasha Vinik @whenharrydumpedsallypod Hosted on Acast. See acast.com/privacy for more information.

The Holiday
Last Tuesday at 12:00 PM

This week we got into THE HOLIDAY spirit and watched The Holiday! We discuss the unrequited love, long-distance relationships, and why swearing on someone’s life isn’t actually that big of a deal. Will Iris and Miles stop falling for walking red flags and live happily ever after? Can Graham and Amanda make long distance work?? Listen to find out!

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Lez Bomb
11/25/2025

This week we watched Lez Bomb! We discuss regressing around family, eating pie for breakfast, and THANKSGIVING. Will Hailey and Lauren actually move in with each other and stay together forever?? Listen to find out!

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You've Got Mail
11/18/2025

Is it possible to forgive the man who destroyed your business and ultimately fall in LOVE?? Apparently in You've Got Mail it IS. We discuss pre-social media internet, decaf coffee drinkers, and emotional infidelity. Will Joe and Kathleen's online romance make up for their real life feud? Will they be together FOREVER?? Listen to find out!

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Dear John
11/11/2025

It’s Veteran’s Day so this week we watched Dear John to SUPPORT THE TROOPS. We discuss intrusive thoughts, kissing in the rain, and how long John and Savnnah will stay together after the credits roll!

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My Date with the President's Daughter
11/04/2025

What would you do if you found out your date was actually the president’s daughter (and maybe the worst person ever)!? This week we watched the made-for-tv romcom, My Date with the President’s Daughter! We discuss why people hate California, our very different opinions on magicians, and how long normie Duncan and first daughter Hallie will stay together after the credits roll!

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Blink Twice
10/29/2025

We ended October with a psychological thriller that has no rom OR com. It’s Blink Twice! We discuss pretending to be happy to protect yourself around men, how the body LOVES keeping the score, and why you should BELIEVE WOMEN. Will Slater and Frida live (happily????) ever after? Listen to find out!

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You're Killing Me
10/21/2025

If a random man stalked you and then told you he was a serial killer would you believe him?? Not if you’re George! This weeks movie is You’re Killing Me! We learn about the difference between jail and prison, discuss why game nights aren’t that fun, and decide whether or not serial killers are HOT. Will George and Joe’s relationship make it through a (probably lifelong) prison sentence?? Listen to find out!

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Zombieland (Fixed)
10/14/2025

Can you survive AND find love in a ZOMBIE APOCALYPSE?? Columbus and Wichita are here to prove it’s possible! This week we watched Zombieland and talked about INCELS, GUNS, and CHATGPT (all sure signs of the impending apocalypse). Will Columbus and Wichita spend the rest of their (probably short) lives together?? Listen to find out!

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Zombieland
10/14/2025

Can you survive AND find love in a ZOMBIE APOCALYPSE?? Columbus and Wichita are here to prove it’s possible! This week we watched Zombieland and talked about INCELS, GUNS, and CHATGPT (all sure signs of the impending apocalypse). Will Columbus and Wichita spend the rest of their (probably short) lives together?? Listen to find out!

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Heart Eyes
10/07/2025

It’s officially SPOOKY SEASON and we’re celebrating all month by watching horror-rom-coms. This week’s terrifying love story is Heart Eyes! We discuss attachment styles, Halloween costumes, and why Valentine’s Day was WAY BETTER as a child. Will Ally and Jay (a couple that is not actually a couple but is being pursued by a killer who murders couples) stay together forever? Listen to find out!

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He's Just Not That Into You
09/30/2025

This week’s movie has a HUGE cast of A-list actors playing AWFUL people. It’s He’s Just Not That Into You! Join us as we try to keep character names and plot lines straight, discuss people who are desperate to find love, and debate how important faces are for one night stands. Plus MySpace, landlines, and BUTTS. How long will the many (but actually only two) couples stay together after the credits roll?? Listen to find out!

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Better Than Chocolate
09/23/2025

This week we watched Better Than Chocolate! We discuss why chocolate isn’t actually that good, clueless moms, and what to do if you overhear your family members having sex! How long will the ULITMATE U-HAULERS Maggie and Kim stay together after the credits roll? Listen to find out!

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The Mummy
09/16/2025

This week we watched The Mummy! What happens when a professional CRIMINAL goes on an adventure with a HOT LIBRARIAN and her VERY DUMB brother?? We discuss Egyptian mythology, LinkedIn influencers, and our THIRD bad(ish?) Ben! How long will Nick and Evelyn stay together after the credits roll? Is the real couple in this movie the Mummy and Anck-su-namun?? Listen to find out!

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Sixteen Candles
09/09/2025

This week we watched Sixteen Candles. We were expecting it to be problematic and BOY did it deliver! We discuss 16th birthday parties, passing notes in class, and how long Samantha and Jake will stay together after the credits roll! All that plus racism, the Me Too movement, and cancel culture?? HOW FUN.

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Always Be My Maybe
08/26/2025

This week we watched Always Be My Maybe and found out if childhood besties are meant to be together forever! We discuss dirty cars, caring too much about filming locations as you get older, and KEANU REEVES. How long will celebrity chef Sasha and normal guy Marcus stay together after the credits roll?? Listen to find out!

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High Fidelity
08/19/2025

Today’s movie is a huge win for problematic men! It’s High Fidelity! We discuss “nice guys” who finish last, “nice guys” who are secretly manipulative monsters, and “nice guys” who finally realize that women are people too! How long will “nice guy” Rob stay with Laura?? Listen to find out!

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Life or Something Like It
08/12/2025

What would you do if you found out you had one week left to live?? We’re getting into that and MORE in this week’s episode about Life or Something Like It. We discuss PSYCHICS, getting black out DRUNK, and giving up your career for LOVE. How long do we think Lanie and Pete will stay together after the credits roll? Listen to find out!

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10 Things I Hate About You
08/05/2025

This week we watched 10 Things I Hate About You and discussed TWO classic teen relationships. We talk about high school cliques, men who blame women’s emotions on PMS, and whether or not younger siblings know anything about their older siblings. How long will popular Bianca and nerdy Cameron stay together? Will bad boy Patrick and angry feminist Kat last forever? Listen to find out!

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Along Came Polly - Full Ep
07/29/2025

Do opposites attract? Can people ever change?? These are the important questions raised in Along Came Polly! We discuss SHARTING, men’s bathrooms, AND how long Reuben and Polly will stay together after the credits roll!

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Along Came Polly
07/29/2025

Do opposites attract? Can people ever change?? These are the important questions raised in Along Came Polly! We discuss SHARTING, men’s bathrooms, AND how long Reuben and Polly will stay together after the credits roll!

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Step Up
07/22/2025

This week we watched Step Up! It’s one of those rare occasions where you wish a movie had LESS plot and MORE dancing. We talk about “phone movies”, Chekhov’s tights, and why having Cornell as your safety school is totally the same as growing up in foster care. Will Tyler and Nora keep dating (and dancing) forever?? Listen to find out!

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Imagine Me & You
07/15/2025

Do you believe in love at first sight?? Luce and Rachel do! This week we are watching (and singing) Imagine Me & You. We discuss setting up your friends, the secret meanings of emojis, and how long Luce and Rachel will stay together after the credits roll!

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My Best Friend's Wedding
07/08/2025

This week we are celebrating unhinged women with My Best Friend’s Wedding! Can you be “best friends” with an ex you still have feelings for? Was this movie supposed to be a musical? How do we feel about JELL-O??? We discuss all this AND how long we think Kimberly and Michael’s marriage will last after the credits roll!

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Materialists
07/01/2025

This week we went to an ACTUAL THEATER and watched Materialists! We ask important questions like, are relationships just math? Should you date someone for their money? And is plastic surgery worth it or kind of sad? How long will cynical Lucy and poor John stay together after the credits roll? Listen to find out!

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D.E.B.S.
06/24/2025

This week we’re talking about D.E.B.S. aka Discipline, Energy, Beauty, Strength aka Spy Kids but make it hot lesbians. We discuss why spies have to be boring people, if crime is a good hobby, and whether or not Australia should exist. How long will Amy (the world’s BEST SPY) and Lucy (the world’s MOST EVIL VILLAIN) stay together after the credits roll? Listen to find out!

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Boy Meets Girl
06/17/2025

We’re getting caught in a LOVE TRIANGLE this week between Ricky, her bestie Robby, who won’t admit he likes her, and Francesca, a rich girl who is engaged to a transphobic marine that secretly hooked up with Ricky in high school. We discuss 2014 fashion, 2014 homophobia, and why you should always hide videos you want to keep private in folders that aren’t obviously labled on your DESKTOP. Who will end up with who?? And will they they stay together forever?? Listen to find out!

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Love Lies Bleeding
06/10/2025

This week we are stretching the meaning of romcom to it’s breaking point and discussing Love Lies Bleeding. Was this requested? Did we add it to our movie list? Who knows! We talk about gym culture, drinking milk, and BUGS. Will Lou and Jackie stay together after their killing spree? Listen to find out!

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Red, White, & Royal Blue
#16
06/03/2025

Can the first son of the United States and the Prince of Wales set aside their differences and go from enemies… to lovers?? We discuss forbidden love, the royal family, and how nice it would be to live in a timeline where a woman is president. How long will Alex and Henry stay together after the credits roll? Listen to find out!

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Twister
#15
05/27/2025

Anchor yourself to a pole and watch out for flying cows, because we’re discussing Twister (the hot spot)! We talk about TORNADOS (duh), women advocating for themselves (we love), and why men should go to therapy (seriously, do it). Will Jo and Bill stay together once their days of chasing storms are over? Listen to find out!

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Miss Congeniality
#14
05/20/2025

Put on some heels and dust off your internalized misogyny, it’s time for Miss Congeniality! We discuss beauty pageants, being a guy's girl, and the power of female friendships. Will Gracie and Eric stay together once she’s no longer in a pageant and adhering to traditional beauty standards? Listen to find out!

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She's The Man
#13
05/13/2025

Get ready for some dramatic irony and hijinks, because we’re watching She’s The Man this week! We discuss important things like SPORTS! HIGH SCHOOL! KISSING BOOTHS! And most importantly, how long Viola and Duke will stay together after the credits roll!

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Notting Hill
#12
05/06/2025

Can a famous movie star and a humble bookstore owner fall in love and stay together forever?? We discuss the importance of finding a man who has friends, embracing cringe, and whether or not we would take a bath at a random man’s apartment. How long will Anna and Will stay together after the credits roll? Listen to find out!

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Serendipity
#11
04/29/2025

Do you believe in FATE and DESTINY? This week we’re discussing Sara and Jonathan’s 5 hour romance that had such a lasting impact they are still thinking about it an unclear number of years later. Join us as we search for signs form the universe and discuss friends who support you even when you’re being insane, public proposals, and how long these two are destined to be together after the credits roll!

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While You Were Sleeping
#10
04/22/2025

Is it ok to lie about being a man in a coma’s fiance? Multiple people in While You Were Sleeping think the answer is YES. We’re celebrating Christmas in April this week and discussing people who are desperate to get married, passport stamps, and whether or not Lucy and Jack will stay together forever!

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The Graduate
#9
04/15/2025

We are flipping the script this week and supporting WOMEN IN MALE FIELDS (being a creep towards your friends’ barely legal kid). We discuss whether or not it’s weird to date someone who banged your mom, if cinematography is enough to make a movie good, and decide how long Ben and Elaine will stay together after the credits roll! It’s a CLASSIC. It’s WILD. It’s THE GRADUATE.

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Crazy, Stupid, Love
#8
04/08/2025

We're tackling TWO relationships in this crazy, stupid, movie! We discuss pickup artists, jumping out of moving vehicles, and the correct way to approach a woman at a bar (spoiler alert: you probably shouldn't). Can Cal and Emily save their marriage? Will Hannah and Jacob make it work?? Listen to find out!

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But I'm a Cheerleader
#7
04/01/2025

Come with us to True Directions, the gayest conversion camp ever! We discuss straight people apparently existing, how hard it can be to figure out your sexuality in a heteronormative world, and how long Megan and Graham will stay together after the movie ends!

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The Proposal
#6
03/25/2025

Is a weekend in Alaska with your boss who you once described as "Satan's Mistress" all it takes to fall in love? Join us for our discussion on why first kisses suck, fart positive relationships, and whether or not we think Margaret and Andrew are destined to be together forever!

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The Wedding Singer
#5
03/18/2025

In this week's episode we are throwing it back to 1998 throwing it back to 1985! We discuss wedding bands vs DJs, sexual harassment, and what the Hulk looks like naked. Is wanting to get married and not drinking very much the recipe for a lasting relationship? Listen to find how long we think Robbie and Julia will stay together after the credits roll!

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Crazy Rich Asians
#4
03/11/2025

Should you tell your partner that your family is crazy rich before introducing them? Nick doesn't think so! We discuss whether or not that's a dealbreaker, boy mom culture, and the ideal bachelorette party. How long do Nick and Rachel stay together after this movie ends?? Listen to find out!

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