Second Date Update: Patrick and Lisa (Vacation No No)
Dec 24, 2025 Photo: Kar-Tr / iStock / Getty Images One of our listeners planned a first date to last 5 full days with a woman he had never even...
Second Date Update: Simone and Jack (High School Holiday Hangout)
Dec 23, 2025 Photo: Getty Images One of our listeners thought inviting a guy over might save her from spending time with her parents while home for the holidays… but...
Second Date Update: Paul and Taylor (Lonely Cannoli)
Dec 22, 2025 Photo: Dean Mitchell / E+ / Getty Images A quick trip to move his car ended up being a HUGE mistake for our listener Paul, and it...
Second Date Update: Drew & Sonia (Street Walker Love Story)
Dec 19, 2025 Photo: Deagreez / iStock / Getty Images One of our listeners turned a super awkward moment into an actual MEET CUTE that almost seemed TOO perfect. You’ll...
Second Date Update: Para and Bryce (Deck the Mall)
Dec 18, 2025 Photo: Getty Images Imagine if you went on a date with a coworker and after the hang out, MULTIPLE PEOPLE are now avoiding you. It happened to...
Second Date Update: Brian and Aubrey (The Boy Who Cried Tree)
Dec 16, 2025 Photo: Getty Images After we totally botched a Second Date Update for a guy a few months ago, he’s back and at this point we’re not sure...
Second Date Update: Karly and Ethan (Dragon Thumbs and Aroma Chums)
Dec 15, 2025 Photo: The Good Brigade / DigitalVision / Getty Images One of our listeners made her date laugh so hard that something embarrassing slipped out and she’s worried...
Second Date Update: Gabe and Abby (Super Kid Shames The Day)
Dec 11, 2025 Photo: Getty Images A random child walked up to Gabe and Abby’s table during a romantic dinner and said something that threw off their ENTIRE EVENING. Is...
Second Date Update: Evan and Jenna (3rd Times A Yawn)
Dec 9, 2025 Photo: Doucefleur / iStock / Getty Images Evan told us he’s fed up with being friend-zoned, and he wants to get ahead of things with a bizarre...
Second Date Update: Alaina and Trey (20 Treadmills of Love)
Dec 4, 2025 Photo: Getty Images Alaina was SHOCKED when she got a look inside Trey’s home but he swears his collection isn’t weird. Find out what it is in...
Second Date Update: Kelly and Brad (Double Roasted Turkey)
Photo: Getty Images One of our listeners met a guy in a peculiar way… by SAVING HIS LIFE! But why doesn’t he ever want to see her again? We’ll use...
Second Date Update: Camilla and Rob (Cutecumber Couple)
Nov 28, 2025 Photo: skynesher / E+ / Getty Images One of our listeners says he got his inspiration for his dating “MOVE” by watching on video online and gathering...
Second Update Update: Zach and Bethany (Second Date First Date Redate)
Nov 26, 2025 Photo: mapodile / E+ / Getty Images The guy in today’s Second Date Update has been on the show before, but today he gets the special opportunity...
Second Date Update: Nate and Laurie (Driving Miss Laurie)
Nov 25, 2025 Photo: Erik Snyder / The Image Bank / Getty Images One of our listeners said he changed ONE THING on his dating profile that instantly changed the...
Second Date Update: Nate and Laurie (Driving Miss Laurie)
Nov 25, 2025 Photo: Erik Snyder / The Image Bank / Getty Images One of our listeners said he changed ONE THING on his dating profile that instantly changed the...