My Worst Date

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

December 31, 2025 42 mins
Closing out 2025 with a perfect movie - join Keegan, Cassi and Christina for a watch of When Harry Met Sally and from everyone at My Worst Date, have a happy new year! Learn more about your ad choices. Visit megaphone.fm/adchoices
Mark as Played
This week Keegan, Cassi and Christina talk about theater kid cringe moments and play FMK with favorite Rob Reiner movies. Going into the bad dates, Cassi shares the drama from a restaurant's holiday party, Christina shares a date that shows all the red flags in relation to her friend's husband and Keegan shares a date getting third-wheeled by a dog. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Sara...
Mark as Played
December 17, 2025 84 mins
This week Keegan, Cassi and Christina discuss surviving the holidays and how terrible shopping has become. The FMK is between holiday songs O, Holy Night, Charlie Brown Christmas and All I Want For Christmas Is You. Going into the bad dates, Keegan shares a date that peed the bed, Cassi shares a story of a boss bringing his girlfriend (not his wife) to the holiday party and Christina shares a girl who turned it all the way up at ...
Mark as Played
December 10, 2025 82 mins
Check out today's sponsor, Beducated: https://beducate.me/worstdate code worstdate for 60% off! This week Keegan, Cassi and Christina discuss how awful it is when your partner's family is your biggest bully, pranks and superstitions. The FMK is between Nicholas Hoult, Bill Pullman and Jon Stewart. Going into the bad dates, Christina shares a depressing date bowling, Keegan shares a back on the dating scene list of assholes and C...
Mark as Played
December 8, 2025 32 mins
We're back! In this bite size episode, Keegan, Cassi and Christina talk holiday party potlucks, drama and shenanigans and laugh about clueless dates, finger foods, the Heimlich maneuver and spaghetti noodles. Learn more about your ad choices. Visit megaphone.fm/adchoices
Mark as Played
December 3, 2025 39 mins
You asked for it and we delivered. In this bonus tainted love movie episode from our Patreon feed, we cover the Christmas sensation, Hot Frosty! Happy Holidays, Worsties! We will return with a brand new episode next week, and appreciate your understanding as we navigate a rollercoaster of a year - we love you so much! Learn more about your ad choices. Visit megaphone.fm/adchoices
Mark as Played
November 26, 2025 70 mins
My Worst Date… in SPACE!! This week Keegan and Christina join the show Too Stupid to Live to answer the MOST IMPORTANT question of all time: What happens when a super chill and easygoing person gets ABDUCTED BY ALIENS?! Today the show reviews Renegade Love ($2.99) by Ann Aguirre.   Book: Renegade Love by Ann Aguirre Amazon Paperback To find Becky and Too Stupid to Live: Apple Podcasts Spotify YouTube ...
Mark as Played
November 19, 2025 100 mins
This week Keegan, Cassi and Christina discuss a date not offering food and beige flags. The FMK is between Stuffing, Mashed Potatoes and Gravy and Macaroni & Cheese. Going into the bad dates, Cassi shares a date full of sex facts, Keegan shares an AOL catfish and Christina shares a rollercoaster date at a Peddler's Mall. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Simeonette Mapes-Crupi. Learn more...
Mark as Played
November 12, 2025 100 mins
This week Keegan, Cassi and Christina discuss going out rules, improv sex lives and Halloween costume wins. The FMK is between Nick Kroll, Nick Offerman and Matthew Lillard.  Going into the bad dates, Keegan shares a date in a shed, Christina shares a role reversal date and Cassi shares a date with an extensive list of everything that's wrong. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Celeste Ma...
Mark as Played
November 5, 2025 82 mins
This week Keegan, Cassi and Christina discuss if having a boyfriend is embarrassing and what the rules for hugging your friend's husband are. The FMK is between Scorpios Joaquin Phoenix, Gerard Butler and Penn Badgely. Going into the bad dates, Christina shares a date with a man fresh out of a breakup, Keegan shares a date swiping Tinder on the date, and Cassi shares a date seeking a sensual lover. Christina wraps it up in the tr...
Mark as Played
October 29, 2025 97 mins
This week Keegan, Cassi and Christina talk about Lily Allen's very detailed new album about David Harbour and why you shouldn't wrong a musician. The FMK is between red flag guys from the 80s, 90s and 00s. Going into the bad dates, Cassi shares a date that can't shake a bad gut feeling, Keegan shares an awful dinner date with surprise ingredients and Christina shares a date built up for 2 years that slowly deflates on an air matt...
Mark as Played
October 22, 2025 81 mins
This week Keegan, Cassi and Christina go through a wild Am I The Asshole question and play FMK with David Cross, Weird Al Yankovic and Paul Scheer. Going into the bad dates, Christina shares a Snapchat truth or dare, Keegan shares a date that goes from love bombing to absolute psycho and Cassi shares a date with kissing cousins. Christina wraps it up in the true crime segment, Tainted Love, with the story of Marie Spannhake. Lea...
Mark as Played
October 15, 2025 86 mins
This week Keegan, Cassi and Christina talk about the new Taylor Swift album and the dangers of being dickmatized. The FMK is between Keke Palmer, Megan Thee Stallion and Hayley Williams. Going into the bad dates, Keegan shares a disappearing movie date, Cassi shares a date that's mega racist and Christina shares a date with a wild open door policy. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Mauric...
Mark as Played
October 8, 2025 85 mins
This week Keegan, Cassi and Christina talk about AI companions and love scams. The FMK is between Keith Urban, Tom Cruise and Lenny Kravitz. Going into the bad dates, Cassi shares a date with a troubled married dude, Christina shares a hungover date and Keegan shares a date that can do impressions...maybe. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Evie Watson. Learn more about your ad choices. Vis...
Mark as Played
October 6, 2025 24 mins
In this bite-sized episode Keegan, Cassi and Christina talk about the Burning Man Orgy Tent and jump into bad dates featuring model portfolios, surprise Porky Pigs, cosigning loans, soiled jeans, red pills at Olive Garden, unicorns, car troubles and secret wives. Learn more about your ad choices. Visit megaphone.fm/adchoices
Mark as Played
October 1, 2025 88 mins
This week Keegan, Cassi and Christina talk going out etiquette and cringe culture. The FMK is between Rivers Cuomo, Alanis Morissette and Nick Hexum. Going into the bad dates, Christina shares a guy with the longest breakup text ever, Cassi shares a terrible repeat date and Keegan shares a guy's smelly turn off. Christina wraps it up in the true crime segment Tainted Love with the story of Seemona Sumasar. Learn more about your ...
Mark as Played
September 24, 2025 93 mins
This week Keegan, Cassi and Christina update about the Irish matchmaking festivals and talk aliens and the rapture. The FMK is between Libras Bruce Springsteen, Brie Larson and Glen Powell. Going into the bad dates, Keegan shares a gold digging date at Applebee's, Cassi shares a high school date getting one-upped by a friend and Christina shares a date with interesting condom techniques. Keegan wraps it up in the true crime segmen...
Mark as Played
September 17, 2025 100 mins
This week Keegan, Cassi & Christina talk sex toys and body modification. The FMK is between short kings Marc Maron, Mark Ruffalo and James McAvoy.Going into the bad dates Cassi shares a date that just won't or can't stop talking, Kegan shares a date with surprise kids and Christina shares a date with a very memorable entrance. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Charlene Childers.Interested ...
Mark as Played
September 10, 2025 77 mins
This week Keegan, Cassi and Christina talk about hygiene drama on TikTok and Ireland's matchmaking festival. The FMK is between Pierce Brosnan, Paul Mescal and Cillian Murphy. Going into the bad dates, Christina shares an awkward teenage date to the movies, Cassi shares a date throwing up into a fender bender and Keegan shares a date with surprise roommate. Christina wraps it up in the true crime segment, Tainted Love, with the s...
Mark as Played
September 3, 2025 91 mins
This week Keegan, Cassi and Christina discuss a reddit thread about a sister being uninvited to family functions due to husband's kink and play fmk with a foot fetish, exhibitionism and BDSM. Going into the bad dates, Keegan shares a date that left early to get back to an ex, Christina shares a chaos goblin on a road trip to Florida and Cassi shares a date from an actual horror movie. Keegan wraps it up in the true crime segment, T...
Mark as Played

Popular Podcasts

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    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

    The Burden

    The Burden is a documentary series that takes listeners into the hidden places where justice is done (and undone). It dives deep into the lives of heroes and villains. And it focuses a spotlight on those who triumph even when the odds are against them. Season 5 - The Burden: Death & Deceit in Alliance On April Fools Day 1999, 26-year-old Yvonne Layne was found murdered in her Alliance, Ohio home. David Thorne, her ex-boyfriend and father of one of her children, was instantly a suspect. Another young man admitted to the murder, and David breathed a sigh of relief, until the confessed murderer fingered David; “He paid me to do it.” David was sentenced to life without parole. Two decades later, Pulitzer winner and podcast host, Maggie Freleng (Bone Valley Season 3: Graves County, Wrongful Conviction, Suave) launched a “live” investigation into David's conviction alongside Jason Baldwin (himself wrongfully convicted as a member of the West Memphis Three). Maggie had come to believe that the entire investigation of David was botched by the tiny local police department, or worse, covered up the real killer. Was Maggie correct? Was David’s claim of innocence credible? In Death and Deceit in Alliance, Maggie recounts the case that launched her career, and ultimately, “broke” her.” The results will shock the listener and reduce Maggie to tears and self-doubt. This is not your typical wrongful conviction story. In fact, it turns the genre on its head. It asks the question: What if our champions are foolish? Season 4 - The Burden: Get the Money and Run “Trying to murder my father, this was the thing that put me on the path.” That’s Joe Loya and that path was bank robbery. Bank, bank, bank, bank, bank. In season 4 of The Burden: Get the Money and Run, we hear from Joe who was once the most prolific bank robber in Southern California, and beyond. He used disguises, body doubles, proxies. He leaped over counters, grabbed the money and ran. Even as the FBI was closing in. It was a showdown between a daring bank robber, and a patient FBI agent. Joe was no ordinary bank robber. He was bright, articulate, charismatic, and driven by a dark rage that he summoned up at will. In seven episodes, Joe tells all: the what, the how… and the why. Including why he tried to murder his father. Season 3 - The Burden: Avenger Miriam Lewin is one of Argentina’s leading journalists today. At 19 years old, she was kidnapped off the streets of Buenos Aires for her political activism and thrown into a concentration camp. Thousands of her fellow inmates were executed, tossed alive from a cargo plane into the ocean. Miriam, along with a handful of others, will survive the camp. Then as a journalist, she will wage a decades long campaign to bring her tormentors to justice. Avenger is about one woman’s triumphant battle against unbelievable odds to survive torture, claim justice for the crimes done against her and others like her, and change the future of her country. Season 2 - The Burden: Empire on Blood Empire on Blood is set in the Bronx, NY, in the early 90s, when two young drug dealers ruled an intersection known as “The Corner on Blood.” The boss, Calvin Buari, lived large. He and a protege swore they would build an empire on blood. Then the relationship frayed and the protege accused Calvin of a double homicide which he claimed he didn’t do. But did he? Award-winning journalist Steve Fishman spent seven years to answer that question. This is the story of one man’s last chance to overturn his life sentence. He may prevail, but someone’s gotta pay. The Burden: Empire on Blood is the director’s cut of the true crime classic which reached #1 on the charts when it was first released half a dozen years ago. Season 1 - The Burden In the 1990s, Detective Louis N. Scarcella was legendary. In a city overrun by violent crime, he cracked the toughest cases and put away the worst criminals. “The Hulk” was his nickname. Then the story changed. Scarcella ran into a group of convicted murderers who all say they are innocent. They turned themselves into jailhouse-lawyers and in prison founded a lway firm. When they realized Scarcella helped put many of them away, they set their sights on taking him down. And with the help of a NY Times reporter they have a chance. For years, Scarcella insisted he did nothing wrong. But that’s all he’d say. Until we tracked Scarcella to a sauna in a Russian bathhouse, where he started to talk..and talk and talk. “The guilty have gone free,” he whispered. And then agreed to take us into the belly of the beast. Welcome to The Burden.

    SmartLess

    "SmartLess" with Jason Bateman, Sean Hayes, & Will Arnett is a podcast that connects and unites people from all walks of life to learn about shared experiences through thoughtful dialogue and organic hilarity. A nice surprise: in each episode of SmartLess, one of the hosts reveals his mystery guest to the other two. What ensues is a genuinely improvised and authentic conversation filled with laughter and newfound knowledge to feed the SmartLess mind. Subscribe to SiriusXM Podcasts+ to listen to new episodes of SmartLess ad-free and a whole week early. Start a free trial now on Apple Podcasts or by visiting siriusxm.com/podcastsplus.

    The Breakfast Club

    The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

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

Connect

© 2026 iHeartMedia, Inc.