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Second Date Update: Sushi & Steve
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Awkward Tuesday: Enhancement Anxiety
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Second Date Update: Surprise Surprise
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FULL SHOW: Horror Movie Date, Jeff’s Discount Humiliation + Brooke's Pickleball Shame (8/5/26)
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Second Date Update Classics: Floral Intentions + Lipstick Dipstick
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Second Date Update Classic: Second Chance Scott
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Textual Healing: Proposal Predicament
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Second Date Update: Movie Mayhem
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Awkward Tuesday: Birthday Tip
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Second Date Update: Kiss GPT
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FULL SHOW: Jeff’s Spider-Man Song, Park Mugging Date + Craziest Pet Owner Demands (7/31/26)
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Second Date Update Classics: Soulmate Psychic + Can I Cut In Lime
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Second Date Update: My Type of Weird
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Second Date Update UPDATE: Does This Smell Like Ur Mom?
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Second Date Update: Mom Blocked
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Awkward Tuesday: Date My Ex PLEASE
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Second Date Update: Nanny No No
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FULL SHOW: Jeff’s Jimothy Parody Song, Dated Your Roomie Date + State Fair Foods (7/24/26)
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Second Date Update Classics: Hearts & Crafts + One More Refill
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Second Date Update: Special Friend Fun
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Brooke Breaks You Up: High School Drama
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Second Date Update: Jiu-Jitsu and Chill
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Awkward Tuesday: Awkward Family Reunion
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Second Date Update: Greek Meat
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Second Date Update Classics: Offer He Can't Refuse + Sea Meat Surprise
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Second Date Update: Bidding On Brandy
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Awkward Thursday: Convince The Sis
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Second Date Update: Case of the Solo Shoe
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Awkward Tuesday: JFK & Oprah the Assassin
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Second Date Update: Car Wash Crush
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FULL SHOW: Voice Note Ick Date, Alexis Personal Love Island + Jeff’s New Beef (7/8/26)
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Second Date Update Classics: Randall Is Back + Highs & Lowells Of Dating
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Second Date Update: Anti-Farmers Market
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Second Date Update UPDATE: He Bought Me A Star
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Second Date Update: Voice Note No No
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Awkward Tuesday: 40th Birthday Blunder
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Second Date Update: Tap It or Scratch It
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FULL SHOW: Undercover Spy Date, Riffin’ Around Summer Edition + Pettiest Neighbors (7/3/26)
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Second Date Update Classics: B Dub Flub + Red Light Green Light
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Second Date Update Classic: I Brought My Mom
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Say Yes To The Ex: Trio Tangle
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Second Date Update Classic: Uber Meets
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Awkward Tuesday: Un-Dump My Ex
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Second Date Update Classic: Dine For One But I'm Not Done
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FULL SHOW: Pursue Me Date, Alexis’ Identity Theft + Jeff’s Mom’s Song of the Week? (6/24/26)
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Second Date Update Classics: A Slip Of The Ex + Putting Together The Pieces
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Second Date Update Classic: Not A Happy Camper
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Am I The Jerk? Save The Announcement
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Second Date Update: Pursue Me Please
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Awkward Tuesday: AI Messed Up
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Second Date Update: Tamogatchi Tea
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FULL SHOW: Brooke Breaks You Up, Whatcha Doin’ at World Cup + Secret Man Crush (6/18/26)
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Second Date Update Classics: Failure To Launch + CSI Dinner Investigation
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Second Date Update Classic: I Dare You To Date Me
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Brooke Breaks You Up: Drop the Stanford Dropout
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Second Date Update: Stroll Club Hero
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Awkward Tuesday: Paging Dr. Luke
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Second Date Update: Shark Tanked
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FULL SHOW: Jeff’s World Cup Song, No Questions EVER Date + Dumbest Political Troll (6/12/26)
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Second Date Update Classics: Big Fragrance Energy + Trying To Connect 4
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Second Date Update: No Questions Ever
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Second Date Update UPDATE: First Base Fam
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Second Date Update: Too Pretty To Tip
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Awkward Tuesday: Surprise Surprise
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Second Date Update: Big Brain vs Semicolon Corey
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FULL SHOW: Jeff’s Class of ’26 Song, Ashton’s Parents vs Dating + Dead Flower Date (6/5/26)
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Second Date Update Classics: Brunch Yuck + Down Under Blunder
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Second Date Update: Three Day Bouquet
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Textual Healing: Breakup Breakfast
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Second Date Update: Capes At Costco
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Awkward Tuesday: Ship My Situationship
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Second Date Update: Door Dash Ashley
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FULL SHOW: Jeffrey’s 1,000th Song, Ashton’s Move Back Home + Divorce Party Date (5/29/26)
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Second Date Update Classics: No Fire In The Fireplace +Best Date Of My Life
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Second Date Update: Can't Beat The Sweet Treat
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Second Date Update UPDATE: Euro Date
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Second Date Update: Defensive Driving Drama
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Awkward Tuesday: Party Hard Granny
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Second Date Update Classic: Senior Moment Slip Up
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FULL SHOW: Mistaken Identity Date, Paid Wedding Crashers + First Bidet Loser Line (5/18/26)
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Second Date Update Classics: Update My Dino Profile + Doodle Worthy
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Second Date Update Classic: Train Game
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Awkward Thursday: 30 Day Girlfriend
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Second Date Update: The Roadside King
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Awkward Tuesday: Something Smells In Canada
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Second Date Update: Mistaken Identity
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FULL SHOW: Corpse Kiss Date, Jeff vs AI Song + Clover DoorDash Detective (5/13/26)
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Second Date Update Classics: I've Dated My Date Before + Two Word Whisperer
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Second Date Update: Ramen Common
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Second Date Update UPDATE: Numbers Don't Lie But You Should
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Second Date Update: Corpse Kiss
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Awkward Tuesday: Surprise Sabotage
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Second Date Update: Strawberry Blowout
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FULL SHOW: Jeff’s Mother’s Day Parody, AI Song For You Date + Gas Station Karen (5/8/26)
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Second Date Update Classics: Flea Market Find + Due The Math
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Second Date Update: Taylor Where'd Ya Go
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Blind Love Is? Brad, Dee & Alexis
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Second Date Update: French Air Kiss
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Awkward Tuesday: Playing Phone Detective
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Second Date Update: Potter Got Hotter
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