My Worst Date
Ever been on a crazy bad date? You're not alone! Join hosts and best friends Keegan Winfield, Christina Conner, and Cassi Young-Paxton as they dish about pop culture, relationships, true crime and share stories from listeners and their past of the worst dating disasters.
Episodes
June 25, 2025 • 75 mins
This week Keegan, Cassi and Christina discuss difficulties in setting boundaries as people pleasers and play FMK with Hermoine Granger, Maleficent and Nancy from The Craft.
Going into the bad dates, there are older married guys getting farting on, ordering extra food to go, washing off hamburgers, sex in public bathrooms, meeting the parents and surprise fiances.
Learn more about your ad choices. Visit megaphone.fm/adchoices
Mark as Played
June 18, 2025 • 71 mins
This week Keegan, Cassi and Christina shout out fantastic listener write ins, and talk about No Kings protests and Tyler's amazing cruise karaoke. The FMK is between cruise lines Carnival, Royal Caribbean and Disney.
Going into the bad dates, Cassi shares a very special private guitar performance, Christina shares a rude date that chooses baseball over the Bachelor and Keegan shares a date that has no boundaries.
Learn more about...
Mark as Played
June 11, 2025 • 57 mins
This week Keegan, Cassi and Christina talk about a date on a budget and the farce of the male loneliness epidemic. The FMK is between Himesh Patel, Jeffrey Wright and Bobby Cannavale. Going into the bad dates, there's a surprise date to a science museum, blue cheese breath, crashing another date, lies about age and a duster date having a bad Tuesday.
Learn more about your ad choices. Visit megaphone.fm/adchoices
Mark as Played
June 4, 2025 • 56 mins
This week Keegan, Cassi and Christina get real about perimenopause and menopause, play FMK with Jean Smart, Helen Mirren and Katey Sagal, and share terrible date stories featuring petty breakups, mouthy divas, Myspace, ethical dilemmas and meeting the parents.
Learn more about your ad choices. Visit megaphone.fm/adchoices
Mark as Played
June 1, 2025 • 34 mins
This bite-sized bonus features bad Bachelor dates and TikTok Grandma drama, and bad date stories with pocket knives, stolen tips and Yaris shootouts.
Learn more about your ad choices. Visit megaphone.fm/adchoices
Mark as Played
May 28, 2025 • 56 mins
This week Keegan, Cassi and Christina discuss both sides of a breakup, play FMK with Geminis Mackelmore, Richard Madden and Michael Cera, and share bad date stories featuring games, parties, first date shits and baby pics.
Learn more about your ad choices. Visit megaphone.fm/adchoices
Mark as Played
May 21, 2025 • 82 mins
This week Keegan, Cassi and Christina talk about TikTok scams and a disappearing husband. The FMK is between Yellowstone, Zion and Sequoia National Parks.Going into the bad date stories, there's surprise spiders, bad jerk off jokes, Troll dolls, stealing stranger's food and experimental jazz.
Learn more about your ad choices. Visit megaphone.fm/adchoices
Mark as Played
May 14, 2025 • 54 mins
This week Keegan, Cassi and Christina discuss 100 Americans vs 100 brits and this year's Met Gala looks. The FMK is between Teyana Taylor, Janelle Monae, and Brian Tyree Henry. Going into the bad dates, Christina shares an observed bad date at a restaurant, Keegan shares a bad date in a tough bathroom situation and Cassi shares a date with way too much going on to be dating.
Learn more about your ad choices. Visit megaphone.fm/adc...
Mark as Played
May 7, 2025 • 94 mins
This week Keegan, Cassi and Christina discuss porn and 100 men versus 1 gorilla. The FMK is between Pools, Lake and Ocean. Going into the bad dates, Cassi shares a date that ruined a blanket fort, Christina shares a date that had to make sure everything was evenly split and Keegan shares a date with a surprise in his pants. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Catherine Martinez.
Learn more ...
Mark as Played
May 5, 2025 • 36 mins
In this bite-sized episode, Keegan, Cassi and Christina discuss faking your death to get out of a hard conversation, laugh about dinosaur conspiracies, and mistaken communication.
Learn more about your ad choices. Visit megaphone.fm/adchoices
Mark as Played
April 30, 2025 • 107 mins
This week Keegan, Cassi and Christina talk about My Strange Addiction, hygiene and baby awards. The FMK is between Fergie, Mariah Carey and Katy Perry.
Going into the bad dates, Keegan shares a relationship where the lie has gone way too far, Cassi shares a date that goes from a play to a peep show and Christina shares a date with mistaken supplements. Keegan wraps it up in the true crime segment, Tainted Love, with the story of ...
Mark as Played
April 23, 2025 • 109 mins
This week Keegan, Cassi and Christina talk about constant flatulence and baby men. The FMK is between Robert Pattinson, Michelle Pfeiffer, and Jamie Dornan.
Going into the bad dates, Christina shares a date with a selfish lover, Cassi shares a relationship ruined by the Satanic Church and Keegan shares a warning about giving that Nice Guy a chance. Christina wraps it up in the true crime segment, Tainted Love, with the story of Cra...
Mark as Played
April 16, 2025 • 93 mins
This week Keegan, Cassi and Christina discuss credit card fraud in relationships and April Fools pranks. The FMK is between John C Reilly, JK Simmons and John Turturro.
Going into the bad dates, Cassi shares an old school date over malts, Christina shares a date with an aging party animal and Keegan shares a date with expensive salmon. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Jeff and Susan Wrig...
Mark as Played
April 9, 2025 • 91 mins
This week Keegan, Cassi and Christina discuss The Group Chat on TikTok and girls' night etiquette. The FMK is between Helena Bonham Carter, Parker Posey and Juliette Lewis.
Going into the bad dates, Keegan shares a hiking date with a trust fund artist, Cassi shares a fancy restaurant date with a Nintendo Switch and Christina shares a Tinder hookup who buried the lead. Keegan wraps it up in the true crime segment, Tainted Love, with...
Mark as Played
April 7, 2025 • 38 mins
Join Keegan, Cassi and Christina in this bite-sized bonus episode to talk about subtext in conversations, and laugh about bad dates with sweaty hands, wet pants, naked parents, pay pigs and roaches.
Learn more about your ad choices. Visit megaphone.fm/adchoices
Mark as Played
April 2, 2025 • 88 mins
This week Keegan, Cassi and Christina discuss the 7 part Hailey Bieber series and bad girl vacations. The FMK is childhood crushes Jonathan Knight, Orlando Bloom and Leonardo DiCaprio.
Going into the bad dates, Christina shares a date that becomes a hate crime, Cassi shares a date with a felon cop and Keegan shares a blind date that ends up somewhere you'd never suspect. Christina wraps it up in the true crime segment, Tainted Lov...
Mark as Played
March 26, 2025 • 101 mins
This week Keegan, Cassi and Christina talk about The Materialists trailer and why there are only 3 acceptable endings. The FMK is for Aries season and is between Jessica Chastain, Keira Knightley and Seth Rogan.
Going into the bad dates, Cassi shares a date that flew to meet a manbaby, Christina shares a date with a dental disaster and Keegan shares a date with guns and the live action Lion King. Cassi wraps it up in the true crime...
Mark as Played
March 19, 2025 • 83 mins
This week Keegan, Cassi and Christina discuss menopause symptoms and period rants. The FMK is between Medusa, Sirens, and Mermaids.
Going into the bad dates, Keegan shares a date with a sweet tooth, Christina shares a date that rudely wakes the house at 4am and Cassi shares a date with too many signs from the universe. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Cathy Wilson.
Learn more about your ...
Mark as Played
March 12, 2025 • 86 mins
This week Keegan, Cassi and Christina talk about memory problems and sex dolls with AI. The FMK is between WALL-E, HER and R2-D2.
Going into the bad dates, Christina shares a date with a super religious guy, Cassi shares a date put on standby and Keegan shares a date that just lets it all go. Christina wraps it up in the true crime segment, Tainted Love, with the story of Kevin Mengel.
Learn more about your ad choices. Visit megaph...
Mark as Played
March 5, 2025 • 116 mins
This week Keegan, Cassi and Christina talk about secrecy in relationships and potatoes. The FMK is between curly fries, waffle fries and tater tots.
Going into the bad dates, Cassi shares a scary date where a different person shows up, Keegan shares a love connection featuring lice, and Christina shares a date with photo albums. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Ali and Ana Abulaban.
Learn...
Mark as Played
Popular Podcasts
Welcome to Bookmarked by Reese’s Book Club — the podcast where great stories, bold women, and irresistible conversations collide! Hosted by award-winning journalist Danielle Robay, each week new episodes balance thoughtful literary insight with the fervor of buzzy book trends, pop culture and more. Bookmarked brings together celebrities, tastemakers, influencers and authors from Reese's Book Club and beyond to share stories that transcend the page. Pull up a chair. You’re not just listening — you’re part of the conversation.
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
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
The latest news in 4 minutes updated every hour, every day.
Listen to 'The Bobby Bones Show' by downloading the daily full replay.