Obsession (2025) with Pilar Alessandra

Jack and Nora are joined by screenwriting coach Pilar Alessandra to wrap up Romcom-oween with a discussion of the indie horror phenomenon Obsession. In this episode, Nora loves an unnecessarily deep read, Jack would let Nikki cut his hair, and Pilar is a little bit freaky. Stock up on duct tape, hug your pets, and let’s make a wish!

Topics include:

• Adaptations of The Monkey’s Paw, from Stephen King to The Simpsons to Curry Barker
• The trope of the “psycho woman” (à la Fatal Attraction)
• What we would wish for

–

Mysteries we still haven’t solved:

• Is everything actually Andy Richter’s fault?
• Is this the highest-grossing film we’ll ever cover?
• Will Inde Navarette be nominated for an Oscar?

–

Content warning: Due to the content of the film, our conversation spans a *range* of disturbing topics including sexual assault/ non-consent, misogyny, drug abuse, self-harm, suicide, murder, and pet death. Tread carefully!

Where to find us:

• Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
• Follow Jack at @thejackgregsonshow
• Follow Nora at @norassic_park
• Follow Pilar at @onthepage (and learn more about her book, online screenwriting classes, and coaching at www.onthepage.tv)

–

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.