Episodes

  • How To Lose a Guy in 10 Days (2003) with Megan Chacalos
    Jan 21 2026

    Jack Jerry and Nora Norason are joined by actor, writer, producer, and TikTok sensation occasionally known as “Olive Oil Girl” Megan Chacalos to discuss #24 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: How To Lose a Guy in 10 Days. In this episode, Nora goes to bat for Kathryn Hahn, Jack advocates for mixed-gender friendships, and Megan actually watched 27 Dresses. Cancel poker night, water your love fern, and let’s get to lost!


    Topics include:

    • Movie taglines
    • Dawson’s Creek
    • Why Megan has a lifetime ban from Tinder

    Mysteries we still haven’t solved:

    • Where is Stanley Tucci right now?

    Where to find us:

    • Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
    • Follow Jack at @thejackgregsonshow
    • Follow Nora at @norassic_park
    • Follow Megan on TikTok at @meganchacalos or Instagram at @meganchacalos (or her podcast at @midnightoilwithmegan)

    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 mail@whenrommet.com.

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

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    1 hr and 10 mins
  • The Apartment (1960) with Charlie Vero Martin
    Jan 14 2026

    Jack and Nora are joined by actor, comedian, and writer Charlie Vero Martin to discuss #25 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: The Apartment. In this episode, Jack finally gets to talk about his favorite romcom, Charlie insists that every drama is really just a bad comedy, and if Mr. Sheldrake has zero haters, then Nora is dead. Hide your spare key, grab a strainer and/or tennis racquet, and let’s find out if that’s the way it crumbles (cookie-wise)!


    Topics include:

    • Rental prices in New York City
    • “Baxters” in romcom writing
    • The ins and outs of spaghetti preparation

    Mysteries we still haven’t solved:

    • Who would we cast if The Apartment was being made today?

    Content Warning: A quick heads up from us— there are several brief references to (but no actual discussions of) a plot point involving attempted suicide, and one mention of abortion.


    Where to find us:

    • Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
    • Follow Jack at @thejackgregsonshow
    • Follow Nora at @norassic_park
    • Follow Charlie at @charlievmartin (and check out her upcoming work-in-progress stand-up show, Poltergeist, at Leicester Comedy Festival!)

    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 mail@whenrommet.com.

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

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    1 hr and 11 mins
  • Enchanted (2007) with Helen Arney & Hannah Roza Fisher
    Jan 7 2026

    Jack and Nora are joined by animator Hannah Roza Fisher and musical theatre writer Helen Arney to discuss #26 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: Enchanted. In this episode, Jack gets creative with pronunciations, Helen is secretly a Disney executive, and Hannah and Nora are co-CEOs of the James Marsden Fan Club. Push up your poofy sleeves, summon a flock of pigeons, and let’s sing a happy little working song!


    Topics include:

    • How animation and musicals (and animated musicals) fit into the world of romcoms
    • Where the one f-bomb should go in this family-friendly film
    • Patrick Dempsey’s hair

    Mysteries we still haven’t solved:

    • Why is Pip from the Bronx?
    • Has anyone ever given a better performance than James Marsden as Prince Edward?
    • Are lips the only thing that touch?

    Where to find us:

    • Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
    • Support the future of the show on Ko-fi
    • Follow Jack at @thejackgregsonshow
    • Follow Nora at @norassic_park
    • Follow Hannah at @hanroza (and check out her animation portfolio at www.hannahroza.com)
    • Follow Helen at @helenarneycomedy (and her new musical at @firebrigademusical orwww.firebrigademusical.com)

    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 mail@whenrommet.com.

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

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    1 hr and 9 mins
  • The Idea of You (2024) with Ashley Hufford
    Dec 3 2025

    Jack and Nora are joined by theatre content creator Ashley Hufford to discuss #27 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: The Idea of You. In this episode, Nora has opinions about onscreen texting, Jack really wants a sandwich, and Ashley doesn’t believe that anyone actually works in an art gallery. Grab your VIP pass, head to Coachella, and let’s feel… everything!


    Topics include:

    • Differences between the book and film
    • Men written by women
    • Having a song in your heart

    Mysteries we still haven’t solved:

    • Why do people hate when women are happy?

    Where to find us:

    • Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
    • Support the future of the show on Ko-fi
    • Follow Jack at @thejackgregsonshow
    • Follow Nora at @norassic_park
    • Follow Ashley at @ashley_hufford, or on TikTok at @ashleyhufford

    Find links to our Spotify playlist, the Vanity Fair list, and more here. Support the future of the show with a one-time or recurring donation on our Ko-Fi.


    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 mail@whenrommet.com.

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

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    1 hr and 2 mins
  • Harold and Maude (1971) with William Webb
    Nov 26 2025

    Jack and Nora are joined by filmmaker William Webb to discuss #28 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: Harold and Maude. In this episode, Nora pitches a circus-themed sequel, Jack has an intuitive grasp of quantum mechanics, and William drops some deep film knowledge. Steal a shovel, hot-wire a car and/or motorcycle, and let’s go dance in a field of daisies!


    Topics include:

    • The Criterion Collection
    • The birth of the “manic pixie dream girl”
    • Neighborhood WhatsApp groups

    Mysteries we still haven’t solved:

    • Is Sunshine Doré alive?

    Content Warning: A quick heads up from us - Harold and Maude is an extremely dark comedy, and death and suicide are major recurring themes. As a result, this episode contains frequent detailed descriptions of suicide and various forms of violent self-injury (mostly fake/ staged by Harold in the story).

    Where to find us:

    • Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
    • Support the future of the show on Ko-fi
    • Follow Jack at @thejackgregsonshow
    • Follow Nora at @norassic_park
    • Follow William at @willwebbful

    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 mail@whenrommet.com.

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

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    1 hr and 3 mins
  • The Big Sick (2017)
    Nov 19 2025

    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"

    Mysteries we still haven’t solved:

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

    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
    • Support the future of the show on Ko-fi
    • Follow Jack at @thejackgregsonshow
    • Follow Nora at @norassic_park

    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 mail@whenrommet.com.

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

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    1 hr and 4 mins
  • Emma. (2020) with Grace O'Keefe
    Nov 12 2025

    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

    Mysteries we still haven’t solved:

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

    Where to find us:

    • Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
    • Support the future of the show on Ko-fi
    • 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)!

    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 mail@whenrommet.com.

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

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    1 hr and 1 min
  • Crazy Rich Asians (2018) with Karen K. Ho
    Nov 5 2025

    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

    Mysteries we still haven’t solved:

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

    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
    • Support the future of the show on Ko-fi
    • 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.)

    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 mail@whenrommet.com.

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

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    57 mins