Brooke and Jeffrey: Second Date Update
2,232 episodes — Page 1 of 45
Awkward Tuesday: Flowers For Who?
Aug 25, 202618 min
Second Date Update Classic: How Dare You Heart Me
Aug 24, 202616 min
FULL SHOW: Monster-In-Law Awkward Call, Get Away Car Confession + Beat Brooke Trivia (8/18/26)
Aug 23, 202653 min
Second Date Update Classics: I Got Cheesecaked + Locked Out Of Love
Aug 22, 202636 min
Second Date Update: A Note For the Waitress
Aug 21, 202619 min
Second Date Update UPDATE: Not So Spicy
Aug 20, 202621 min
Second Date Update: I Went Full Robbins
Aug 19, 202618 min
Awkward Tuesday: Monster In Law
Aug 18, 202619 min
Second Date Update: Smells Like A Hamster
Aug 17, 202618 min
FULL SHOW: Boob Job Shock Awkward Call, Whatcha Doin’ at the Bus Stop + Spanish Tinder (8/11/26)
Aug 16, 202653 min
Second Date Update Classics: Heart Eyes For Air Fries + Motivational Freaker
Aug 15, 202637 min
Second Date Update Classic: Yawn and She's Gone
Aug 14, 202618 min
Closure Call: The Web Date That Got Away
Aug 13, 202618 min
Second Date Update: Sushi & Steve
Aug 12, 202618 min
Awkward Tuesday: Enhancement Anxiety
Aug 11, 202619 min
Second Date Update: Surprise Surprise
Aug 10, 202618 min
FULL SHOW: Horror Movie Date, Jeff’s Discount Humiliation + Brooke's Pickleball Shame (8/5/26)
Aug 9, 20261h 5m
Second Date Update Classics: Floral Intentions + Lipstick Dipstick
Aug 8, 202636 min
Second Date Update Classic: Second Chance Scott
Aug 7, 202618 min
Textual Healing: Proposal Predicament
Aug 6, 202618 min
Second Date Update: Movie Mayhem
Aug 5, 202617 min
Awkward Tuesday: Birthday Tip
Aug 4, 202618 min
Second Date Update: Kiss GPT
Aug 3, 202618 min
FULL SHOW: Jeff’s Spider-Man Song, Park Mugging Date + Craziest Pet Owner Demands (7/31/26)
Aug 2, 20261h 2m
Second Date Update Classics: Soulmate Psychic + Can I Cut In Lime
Aug 1, 202636 min
Second Date Update: My Type of Weird
Jul 31, 202617 min
Second Date Update UPDATE: Does This Smell Like Ur Mom?
Jul 30, 202618 min
Second Date Update: Mom Blocked
Jul 29, 202618 min
Awkward Tuesday: Date My Ex PLEASE
Jul 28, 202618 min
Second Date Update: Nanny No No
Jul 27, 202617 min
FULL SHOW: Jeff’s Jimothy Parody Song, Dated Your Roomie Date + State Fair Foods (7/24/26)
Jul 26, 20261h 5m
Second Date Update Classics: Hearts & Crafts + One More Refill
Jul 25, 202638 min
Second Date Update: Special Friend Fun
Jul 24, 202618 min
Brooke Breaks You Up: High School Drama
Jul 23, 202619 min
Second Date Update: Jiu-Jitsu and Chill
Jul 22, 202618 min
Awkward Tuesday: Awkward Family Reunion
Jul 21, 202618 min
Second Date Update: Greek Meat
Jul 20, 202617 min
Second Date Update Classics: Offer He Can't Refuse + Sea Meat Surprise
Jul 18, 202635 min
Second Date Update: Bidding On Brandy
Jul 17, 202618 min
Awkward Thursday: Convince The Sis
Jul 16, 202618 min
Second Date Update: Case of the Solo Shoe
Jul 15, 202618 min
Awkward Tuesday: JFK & Oprah the Assassin
Jul 14, 202618 min
Second Date Update: Car Wash Crush
Jul 13, 202618 min
FULL SHOW: Voice Note Ick Date, Alexis Personal Love Island + Jeff’s New Beef (7/8/26)
Jul 12, 20261h 7m
Second Date Update Classics: Randall Is Back + Highs & Lowells Of Dating
Jul 11, 202637 min
Second Date Update: Anti-Farmers Market
Jul 10, 202618 min
Second Date Update UPDATE: He Bought Me A Star
Jul 9, 202617 min
Second Date Update: Voice Note No No
Jul 8, 202618 min
Awkward Tuesday: 40th Birthday Blunder
Jul 7, 202618 min
Second Date Update: Tap It or Scratch It
Jul 6, 202618 min