All Episodes

September 16, 2025 13 mins

From giant banners to over-the-top surprises, today’s Chatterbox takes a deep dive into the world of promposals. Why are teens turning a simple “will you go with me?” into a full-blown performance? We share some of the funniest, most awkward, and downright horrifying promposal stories - and wonder if social media is to blame for the rise of this trend.


Grab a drink, laugh with us, and let’s unpack why prom season has become such a spectacle.


Don’t forget to:

✔️ Subscribe for weekly, unfiltered takes on parenting, pop culture and breaking news.

✔️ Comment below — what do YOU think is going wrong with today’s youth?

✔️ Follow us @winechatspodcast on Instagram & TikTok for behind-the-scenes chaos.


🚨 Exciting updates coming your way!

Join our mailing list so you don’t miss out: winechatspodcast.com

💬 Got thoughts on this episode? We’d love to hear them! Email us: winechatspodcast@gmail.com


Music generated by Mubert https://mubert.com/render


#promposals #promposalstories #prom2025 #teenlife #highschooldrama #promseason #awkwardmoments #cringeworthy #funnyfails #socialmediatrends #podcastlife #chatterboxpodcast

Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Are You A Charlotte?

Are You A Charlotte?

In 1997, actress Kristin Davis’ life was forever changed when she took on the role of Charlotte York in Sex and the City. As we watched Carrie, Samantha, Miranda and Charlotte navigate relationships in NYC, the show helped push once unacceptable conversation topics out of the shadows and altered the narrative around women and sex. We all saw ourselves in them as they searched for fulfillment in life, sex and friendships. Now, Kristin Davis wants to connect with you, the fans, and share untold stories and all the behind the scenes. Together, with Kristin and special guests, what will begin with Sex and the City will evolve into talks about themes that are still so relevant today. "Are you a Charlotte?" is much more than just rewatching this beloved show, it brings the past and the present together as we talk with heart, humor and of course some optimism.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.