Jack and Nora are all on their own to discuss #29 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: The Big Sick. In this episode, Nora is the most sex, drugs, and rock ‘n’ roll person Jack has ever met, and Jack outs himself as an Animorph. Grab your in-laws, hop in an Uber, and let’s find the missing cat in the research facility!

Topics include:

• Cheeseburger mishaps
• Arranged marriage
• Judd Apatow and the "boy romcom"

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Mysteries we still haven’t solved:

• Which of our favorite scenes happened in real life vs. being written for the movie? 

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Content Warning: A quick heads up from us— as it is a recurring theme in the film, this episode contains a few brief references to post-9/11 Islamophobia and stereotyping.

Where to find us:

• Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
• Follow Jack at @thejackgregsonshow
• Follow Nora at @norassic_park

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Find links to our Spotify playlist, the Vanity Fair list, and more here.

Join the conversation! Give us your take on the films we cover, which romcoms you think should be on the list, or your best “would do/ wouldn’t do/ have done” stories on socials or at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Jack and Nora are joined by musical comedy writer Grace O’Keefe to discuss #30 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: Emma. In this episode, Nora makes some NSFW noises, Jack auditions to host the MTV Movie Awards, and Grace is bringing bonnets back. Lace up your corset, brush up on your period-appropriate dance moves, and let’s make a match!

Topics include:

• Clueless (1995)
• Regency romance and the female gaze
• Acting so hard you get a nosebleed

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Mysteries we still haven’t solved:

• What IS Mr. Knightley’s hottest moment, actually?

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Where to find us:

• Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
• Follow Jack at @thejackgregsonshow
• Follow Nora at @norassic_park
• Follow Grace at @grace_o_keefe
• Follow @senseandsensibilitymusical to keep up with the journey of the show – and check out the EP dropping on 16th December (Jane Austen’s 250th birthday)!

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Find links to our Spotify playlist, the Vanity Fair list, and more here.

Join the conversation! Give us your take on the films we cover, which romcoms you think should be on the list, or your best “would do/ wouldn’t do/ have done” stories on socials or at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Jack and Nora are joined by business and culture journalist Karen K. Ho to discuss #31 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: Crazy Rich Asians. In this episode, Nora gets on her soapbox, Jack hands out Oscars, and Karen is a paragon of podcast etiquette. Book your VIP suite to Singapore, brush up on your dumpling-rolling technique, and let’s get crazy (rich)!

Topics include:

• The lasting impact of Crazy Rich Asians 
• The drawbacks to doing your grand romantic gesture on a long-haul flight
• Why Constance Wu should be in more movies

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Mysteries we still haven’t solved:

• When are we getting those sequels?!
• Why didn’t this movie get any Academy Award nominations?

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Content Warning: A quick heads up from us— in the context of discussing this film’s plot and social/ historical significance, this episode contains several references to discrimination against and stereotyping of Asians and Asian Americans, particularly in the entertainment industry.

Where to find us:

• Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
• Follow Jack at @thejackgregsonshow
• Follow Nora at @norassic_park
• Follow Karen at @heykarenho (and read Karen’s TIME cover story on Crazy Rich Asians here.)

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Find links to our Spotify playlist, the Vanity Fair list, and more here.

Join the conversation! Give us your take on the films we cover, which romcoms you think should be on the list, or your best “would do/ wouldn’t do/ have done” stories on socials or at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Jack and Nora are joined by performer, writer, and environmentalist Aruhan Galieva to discuss #32 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: Bridget Jones: Mad About the Boy. In this episode, Nora embraces her inner Daniel Cleaver, Jack asks important questions about pie, and Aruhan dishes up hot takes and even hotter owl facts. Round up your oldest pals, order a blue cocktail, and let’s find our second chance at love!

Topics include:

• What exactly constitutes a franchise
• The death of DVD extras
• Hello, Dolly!

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Mysteries we still haven’t solved:

• How many times can you cry before a movie no longer qualifies as a romcom?
• Does anyone other than Mr. Walliker actually work at that school?!

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Content Warning: A quick heads up from us— as a major plot and thematic element of the film, this episode contains frequent references to grief and grieving (specifically, losing a spouse).

Where to find us:

• Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
• Follow Jack at @thejackgregsonshow
• Follow Nora at @norassic_park
• Follow Aruhan at @aruhangalieva. Watch her in Play Time on ITV1 on November 10th (and available on ITVX afterwards), and listen to Time of the Week on BBC Sounds!

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Find links to our Spotify playlist, the Vanity Fair list, and more here.

Join the conversation! Give us your take on the films we cover, which romcoms you think should be on the list, or your best “would do/ wouldn’t do/ have done” stories on socials or at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Jack and Nora are joined by romance author Alexandria Lee to discuss #33 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: Never Been Kissed. In this episode, Nora is extremely picky about lipstick shades, Jack is a certified Guy Perkins hater, and Alexandria gets spicyyyyy. Throw on your fluffiest feather boa, secure your hidden camera pin, and let’s go undercover!

Topics include:

• The allure of forbidden romance
• Great on-screen kisses featuring Drew Barrymore
• The general horniness of renowned film critic Roger Ebert (and Scooby Doo 2: Monsters Unleashed)

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Mysteries we still haven’t solved:

• Did Rob and Tracy make out before prom? (Please say no.)

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Content Warning: A quick heads up from us — as it’s a major plot and thematic element of the film, this episode contains frequent references to romantic relationships between teenagers and adults, as well as discussions of power dynamics, consent laws, and safeguarding.

Where to find us:

• Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
• Follow Jack at @thejackgregsonshow
• Follow Nora at @norassic_park
• Follow Alexandria at @author_alexandrialee (and buy her books on Amazon)

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Find links to our Spotify playlist, the Vanity Fair list, and more here.

Join the conversation! Give us your take on the films we cover, which romcoms you think should be on the list, or your best “would do/ wouldn’t do/ have done” stories on socials or at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Jack and Nora are joined by film historian and publicist Ally Russell to discuss #34 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: The Wedding Banquet. In this episode, Nora is besties with Javier Bardem, Jack is absolutely smitten with Bowen Yang (as are we all), and Ally would like to have words with Ang Lee. Gather your found family, secure your live goose and/or ceremonial wooden duck, and let’s throw a [sham] wedding!

Topics include:

• The original The Wedding Banquet (1993) vs. the reimagining
• Pisces film directors
• Netflix romcoms

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Mysteries we still haven’t solved:

• WHY was that wedding night plot point in the original film?! Like, why???
• Would anyone like to hear our pitch for a Lawyer Sun spinoff series?

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Content Warning: A quick heads up from us — this episode includes a brief discussion of marital sexual assault, in the context of discussing a plot point from the original 1993 film (16:06-18:15). Due to the themes of the film, there are also frequent brief references throughout the episode to pregnancy, infertility and IVF treatments (longer fertility/IVF discussion from 31:23-32:48) and one mention of abortion (22:14-22:25).

Where to find us:

• Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
• Follow Jack at @thejackgregsonshow
• Follow Nora at @norassic_park
• Follow Ally on Letterboxd at @allyrussell

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Find links to our Spotify playlist, the Vanity Fair list, and more here.

Join the conversation! Give us your take on the films we cover, which romcoms you think should be on the list, or your best “would do/ wouldn’t do/ have done” stories on socials or at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Jack and Nora are joined by writer and educator Emily Garside to discuss #35 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: Fire Island. In this episode, Nora is super into Pride and Prejudice, Jack is Captain Straight Man, and Emily gets nerdy about queer culture. Dust off your Speedo and don’t be late for the ferry — we’re going to Gay Disney World!

Topics include:

• Colin Firth
• The Bechdel Test
• Quibi

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Mysteries we still haven’t solved:

• How Will manages to be SO HOT— even when he’s throwing tiny ice cream cones all over the place.

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Content Warning: A quick heads up from us — this episode includes a brief discussion of revenge porn and nonconsensual filming of sexual activity (time stamp: 39:48-41:27). It also includes references to racism towards Asian Americans (16:27-17:04) and size discrimination and diet culture in the LGBTQ+ community (33:32-36:24). These topics are all brought up in the context of discussing plot points and themes from the film. 

Where to find us:

• Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
• Follow Jack at @thejackgregsonshow 
• Follow Nora at @norassic_park
• Follow Emily at @emigarside

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Find links to our Spotify playlist, the Vanity Fair list, and more here. 

Join the conversation! Give us your take on the films we cover, which romcoms you think should be on the list, or your best “would do/ wouldn’t do/ have done” stories on socials or at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Jack and Nora are joined by playwright Grace Aki to discuss #36 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: Defending Your Life. In this episode, Nora gets her best point stolen, Jack is a Men in Black guy, and Grace picks the least uplifting birthday film possible. Put on your tupa, crank some Barbra, and let’s catch the tram to Judgment City!

Topics include:

• The afterlife 
• Bad standup comedy
• Meryl Streep

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Mysteries we still haven’t solved:

• Does Shirley MacLaine hold the key to the afterlife?
• How did they get that baby to do that?

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Where to find us:

• Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
• Follow Jack at @thejackgregsonshow
• Follow Nora at @norassic_park
• Follow Grace at @graceaki (or TikTok at @itsgraceaki)

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Find links to our Spotify playlist, the Vanity Fair list, and more here.

Join the conversation! Give us your take on the films we cover, which romcoms you think should be on the list, or your best “would do/ wouldn’t do/ have done” stories on socials or at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Jack and Nora are joined by actor, writer, and TTRPGer Jen Coles (she/they) to discuss #37 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: Kissing Jessica Stein. In this episode, Nora fangirls over Tovah Feldshuh, Jack channels Tony Soprano, and Jen balances it all out with some truly heartfelt analysis. Stock up on pamphlets, blend those lipsticks, and let’s meet “a very nice girl”!

Topics include:

• Adapting from stage to screen
• Legally Blonde 2: Red, White & Blonde (2003)
• Compulsory heterosexuality

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Mysteries we still haven’t solved:

• What *did* Sex and the City 2 do to Stanford and Anthony?!
• Is arugula actually one of the more expensive greens?

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Where to find us:

• Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
• Follow Jack at @thejackgregsonshow 
• Follow Nora at @norassic_park
• Follow Jen at @jencolescreative

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Find links to our Spotify playlist, the Vanity Fair list, the Kissing Jessica Stein/ Shiva Baby article, and more here. 

Join the conversation! Give us your take on the films we cover, which romcoms you think should be on the list, or your best “would do/ wouldn’t do/ have done” stories on socials or at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Jack and Nora are joined by actor and singer-songwriter Josh St. Clair to discuss the world premiere of 50 First Dates: The Musical. In this episode, Jack finally gets to talk about Adam Sandler, Nora reveals her deep knowledge of Fight Club, and Josh achieves his lifelong goal of getting a Grenade Bar. Order some waffles, head to [redacted tropical location], and let’s fall in love again (for the first time)!

Topics include:

• Great first dates
• Disney World
• Movies we would/ wouldn’t want to be forced to watch every single night

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Mysteries we still haven’t solved:

• How has the musical adapted our favorite moments from the film?!

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Every other film mentioned in this episode: 

Ghost (1990), Groundhog Day (1993), Titanic (1997), The Wedding Singer (1998), Notting Hill (1999), 10 Things I Hate About You (1999), The Sixth Sense (1999), Fight Club (1999), South Park: Bigger, Longer and Uncut (1999), The Princess Diaries (2001), The Princess Diaries 2: Royal Engagement (2004), 13 Going on 30 (2004), The Terminal (2004), Mean Girls (2004), Blended (2014), Space Jam 2: A New Legacy (2021), Juror #2 (2025)

Where to find us:

• Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
• Follow Jack at @thejackgregsonshow 
• Follow Nora at @norassic_park
• Follow Josh at @joshst_clair (and listen to his solo EP wherever you stream music!)
• Find links to our Spotify playlist, the Vanity Fair list, Jack’s Adam Sandler podcast, and more here. 

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Get tickets to see Josh in 50 First Dates: The Musical, 14th September to 16th November at The Other Palace in London (we also recommend TheatreNinja for comparing tickets across dates)!

Join the conversation! Give us your take on the films we cover, which romcoms you think should be on the list, or your best “would do/ wouldn’t do/ have done” stories on socials or at [email protected].

Hosted on Acast. See acast.com/privacy for more information.