All episodes

Second Date Update Classics: Hearts & Crafts + One More Refill

Second Date Update: Special Friend Fun

Brooke Breaks You Up: High School Drama

Second Date Update: Jiu-Jitsu and Chill

Awkward Tuesday: Awkward Family Reunion

Second Date Update: Greek Meat

Second Date Update Classics: Offer He Can't Refuse + Sea Meat Surprise

Second Date Update: Bidding On Brandy

Awkward Thursday: Convince The Sis

Second Date Update: Case of the Solo Shoe

Awkward Tuesday: JFK & Oprah the Assassin

Second Date Update: Car Wash Crush

FULL SHOW: Voice Note Ick Date, Alexis Personal Love Island + Jeff’s New Beef (7/8/26)

Second Date Update Classics: Randall Is Back  + Highs & Lowells Of Dating

Second Date Update: Anti-Farmers Market

Second Date Update UPDATE: He Bought Me A Star

Second Date Update: Voice Note No No

Awkward Tuesday: 40th Birthday Blunder

Second Date Update: Tap It or Scratch It

FULL SHOW: Undercover Spy Date, Riffin’ Around Summer Edition + Pettiest Neighbors (7/3/26)

Second Date Update Classics: B Dub Flub + Red Light Green Light

Second Date Update Classic: I Brought My Mom

Say Yes To The Ex: Trio Tangle

Second Date Update Classic: Uber Meets

Awkward Tuesday: Un-Dump My Ex

Second Date Update Classic: Dine For One But I'm Not Done

FULL SHOW: Pursue Me Date, Alexis’ Identity Theft + Jeff’s Mom’s Song of the Week? (6/24/26)

Second Date Update Classics: A Slip Of The Ex + Putting Together The Pieces

Second Date Update Classic: Not A Happy Camper

Am I The Jerk? Save The Announcement

Second Date Update: Pursue Me Please

Awkward Tuesday: AI Messed Up

Second Date Update: Tamogatchi Tea

FULL SHOW: Brooke Breaks You Up, Whatcha Doin’ at World Cup + Secret Man Crush (6/18/26)

Second Date Update Classics: Failure To Launch + CSI Dinner Investigation

Second Date Update Classic: I Dare You To Date Me

Brooke Breaks You Up: Drop the Stanford Dropout

Second Date Update: Stroll Club Hero

Awkward Tuesday: Paging Dr. Luke

Second Date Update: Shark Tanked

FULL SHOW: Jeff’s World Cup Song, No Questions EVER Date + Dumbest Political Troll (6/12/26)

Second Date Update Classics: Big Fragrance Energy + Trying To Connect 4

Second Date Update: No Questions Ever

Second Date Update UPDATE: First Base Fam

Second Date Update: Too Pretty To Tip

Awkward Tuesday: Surprise Surprise

Second Date Update: Big Brain vs Semicolon Corey

FULL SHOW: Jeff’s Class of ’26 Song, Ashton’s Parents vs Dating + Dead Flower Date (6/5/26)

Second Date Update Classics: Brunch Yuck + Down Under Blunder

Second Date Update: Three Day Bouquet

Textual Healing: Breakup Breakfast

Second Date Update: Capes At Costco

Awkward Tuesday: Ship My Situationship

Second Date Update: Door Dash Ashley

FULL SHOW: Jeffrey’s 1,000th Song, Ashton’s Move Back Home + Divorce Party Date (5/29/26)

Second Date Update Classics: No Fire In The Fireplace +Best Date Of My Life

Second Date Update: Can't Beat The Sweet Treat

Second Date Update UPDATE: Euro Date

Second Date Update: Defensive Driving Drama

Awkward Tuesday: Party Hard Granny

Second Date Update Classic: Senior Moment Slip Up

FULL SHOW: Mistaken Identity Date, Paid Wedding Crashers + First Bidet Loser Line (5/18/26)

Second Date Update Classics: Update My Dino Profile + Doodle Worthy

Second Date Update Classic: Train Game

Awkward Thursday: 30 Day Girlfriend

Second Date Update: The Roadside King

Awkward Tuesday: Something Smells In Canada

Second Date Update: Mistaken Identity

FULL SHOW: Corpse Kiss Date, Jeff vs AI Song + Clover DoorDash Detective (5/13/26)

Second Date Update Classics: I've Dated My Date Before + Two Word Whisperer

Second Date Update: Ramen Common

Second Date Update UPDATE: Numbers Don't Lie But You Should

Second Date Update: Corpse Kiss

Awkward Tuesday: Surprise Sabotage

Second Date Update: Strawberry Blowout

FULL SHOW: Jeff’s Mother’s Day Parody, AI Song For You Date + Gas Station Karen (5/8/26)

Second Date Update Classics: Flea Market Find + Due The Math

Second Date Update: Taylor Where'd Ya Go

Blind Love Is? Brad, Dee & Alexis

Second Date Update: French Air Kiss

Awkward Tuesday: Playing Phone Detective

Second Date Update: Potter Got Hotter

FULL SHOW: Jeff’s Dating Studs Parody, Funny Teacher Confessions + Wrong Way Cruise (5/1/26)

Second Date Update Classics: 1st Impression Means Everything + Dino Drunkfest

Second Date Update Classic: Where Do I Know You From?

Textual Healing: America's Next Top BF

Second Date Update: Practice Makes Perfect

Awkward Tuesday: Amber's Life Alert

Second Date Update: Glad You Didn't Die

FULL SHOW: Jose’s Birthday, Jeff’s Glove Me Bieber Parody+ Steady Eddy Wedding Prank (4/24/26)

Second Date Update Classics: Barwreck + Meal Me Once

Second Date Update: Love At First Height

Second Date Update UPDATE: Hot to Huh

Second Date Update: 49er's For Life

Awkward Tuesday: Speed Date My Ex

Second Date Update: Most Popular Guy In Town

Second Date Update Classics: Yup Date For Jessica + 1 Year Later To Rejection King

Second Date Update Classic: My Wing Mom

Textual Healing: A Different Type of Ghosting

Second Date Update Classic: Hot Date Hijack