Brooke and Jeffrey: Second Date Update
2,175 episodes — Page 1 of 44
FULL SHOW: Pursue Me Date, Alexis’ Identity Theft + Jeff’s Mom’s Song of the Week? (6/24/26)
Jun 28, 20261h 3m
Second Date Update Classics: A Slip Of The Ex + Putting Together The Pieces
Jun 27, 202637 min
Second Date Update Classic: Not A Happy Camper
Jun 26, 202617 min
Am I The Jerk? Save The Announcement
Jun 25, 202617 min
Second Date Update: Pursue Me Please
Jun 24, 202617 min
Awkward Tuesday: AI Messed Up
Jun 23, 202618 min
Second Date Update: Tamogatchi Tea
Jun 22, 202617 min
FULL SHOW: Brooke Breaks You Up, Whatcha Doin’ at World Cup + Secret Man Crush (6/18/26)
Jun 21, 202654 min
Second Date Update Classics: Failure To Launch + CSI Dinner Investigation
Jun 20, 202637 min
Second Date Update Classic: I Dare You To Date Me
Jun 19, 202618 min
Brooke Breaks You Up: Drop the Stanford Dropout
Jun 18, 202619 min
Second Date Update: Stroll Club Hero
Jun 17, 202617 min
Awkward Tuesday: Paging Dr. Luke
Jun 16, 202617 min
Second Date Update: Shark Tanked
Jun 15, 202617 min
FULL SHOW: Jeff’s World Cup Song, No Questions EVER Date + Dumbest Political Troll (6/12/26)
Jun 14, 20261h 4m
Second Date Update Classics: Big Fragrance Energy + Trying To Connect 4
Jun 13, 202637 min
Second Date Update: No Questions Ever
Jun 12, 202618 min
Second Date Update UPDATE: First Base Fam
Jun 11, 202617 min
Second Date Update: Too Pretty To Tip
Jun 10, 202617 min
Awkward Tuesday: Surprise Surprise
Jun 9, 202619 min
Second Date Update: Big Brain vs Semicolon Corey
Jun 8, 202618 min
FULL SHOW: Jeff’s Class of ’26 Song, Ashton’s Parents vs Dating + Dead Flower Date (6/5/26)
Jun 7, 20261h 4m
Second Date Update Classics: Brunch Yuck + Down Under Blunder
Jun 6, 202637 min
Second Date Update: Three Day Bouquet
Jun 5, 202618 min
Textual Healing: Breakup Breakfast
Jun 4, 202619 min
Second Date Update: Capes At Costco
Jun 3, 202618 min
Awkward Tuesday: Ship My Situationship
Jun 2, 202618 min
Second Date Update: Door Dash Ashley
Jun 1, 202618 min
FULL SHOW: Jeffrey’s 1,000th Song, Ashton’s Move Back Home + Divorce Party Date (5/29/26)
May 31, 20261h 3m
Second Date Update Classics: No Fire In The Fireplace +Best Date Of My Life
May 30, 202638 min
Second Date Update: Can't Beat The Sweet Treat
May 29, 202617 min
Second Date Update UPDATE: Euro Date
May 28, 202618 min
Second Date Update: Defensive Driving Drama
May 27, 202617 min
Awkward Tuesday: Party Hard Granny
May 26, 202618 min
Second Date Update Classic: Senior Moment Slip Up
May 25, 202618 min
FULL SHOW: Mistaken Identity Date, Paid Wedding Crashers + First Bidet Loser Line (5/18/26)
May 24, 20261h 5m
Second Date Update Classics: Update My Dino Profile + Doodle Worthy
May 23, 202637 min
Second Date Update Classic: Train Game
May 22, 202617 min
Awkward Thursday: 30 Day Girlfriend
May 21, 202619 min
Second Date Update: The Roadside King
May 20, 202617 min
Awkward Tuesday: Something Smells In Canada
May 19, 202619 min
Second Date Update: Mistaken Identity
May 18, 202618 min
FULL SHOW: Corpse Kiss Date, Jeff vs AI Song + Clover DoorDash Detective (5/13/26)
May 17, 20261h 6m
Second Date Update Classics: I've Dated My Date Before + Two Word Whisperer
May 16, 202636 min
Second Date Update: Ramen Common
May 15, 202618 min
Second Date Update UPDATE: Numbers Don't Lie But You Should
May 14, 202618 min
Second Date Update: Corpse Kiss
May 13, 202618 min
Awkward Tuesday: Surprise Sabotage
May 12, 202618 min
Second Date Update: Strawberry Blowout
May 11, 202618 min
FULL SHOW: Jeff’s Mother’s Day Parody, AI Song For You Date + Gas Station Karen (5/8/26)
May 10, 20261h 6m