Brooke and Jeffrey: Second Date Update
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Episodes
Awkward Tuesday: Mommy Matchmaker
Listener Kim seeks advice after another mom texts her to arrange a formal dinner date between their fourth-grade children.
Second Date Update: Dr. Deb & Yoga Boy
Dr.
FULL SHOW: Jeff’s Starbucks Parody, Missed Kiss Date + Holy Meal Train Prank (11/6/26)
Brooke and Jeffrey discuss a poll on eating from sanitized bowls, play a Monopoly trivia game, and share laser stories including a dinosaur costume brawl and Finland’s dating initiative.
Second Date Update Classics: Brews & Bikes + YouTaboo
Brooke and Jeffrey discuss a listener who accidentally confessed love on a voicemail, leading to a live call where the woman reciprocates his feelings.
Second Date Update: Yikes On Yelp
Paul and Jeffrey discuss Paul's disastrous second date with Terry, where he accidentally dined and dashed due to a cash shortage.
Second Date Update UPDATE: Dirty Danny the Sexy Shoe Salesman
Brooke and Jeffrey revisit Claire and Dan, a couple who met at a shoe store and bonded over playful, maternal behaviors like feeding each other chips and wiping mouths.
Second Date Update: Froyo Fun
Listener Amanda shares her first date with Steve, which involved an intense Froyo session and five hours of dancing.
Awkward Tuesday: Babysitting Blues
In this episode, college student Shelby seeks advice after a babysitting client underpaid her by $60.
Second Date Update: The Set Up
Listener Megan claims her disastrous first date with Richard was a genuine mistake, but the hosts uncover a plot to publicly humiliate him for ghosting her sister.
FULL SHOW: Halloween COSTUME Reveal, Horror Fest Date + Monster (Laser) Stories (10/30/26)
The hosts reveal their group Halloween costumes as Looney Tunes characters, with Brooke dressed as Yosemite Sam and Jeffrey as Bugs Bunny.
Second Date Update Classics: Real Life Ghosting + Halloween Ghostface Ditcher
In this Halloween-themed episode, hosts Brooke and Jeffrey discuss two "Second Date Update" stories.
Second Date Update: Something Sticky Down There
Listener Sean recounts meeting Allie at a horror film fest, but she stopped responding after he jokingly called her "Wednesday" based on her goth attire.
Reverse Trick or Treating
Brooke and Jeffrey return to their "reverse trick-or-treating" tradition, sending their technical director Ashton and his father to convince random homeowners to swap places for a treat.
Second Date Update: Float & Boat
In this Second Date Update, hosts Brooke and Jeffrey call Vince to address why he abruptly left Taylor during a sensory deprivation tank date.
Awkward Tuesday: Haunting of Boyfriends Past
In this Halloween-themed episode, listener Amy calls to discuss her ex-boyfriend Max, who has been posting old photos of them together on social media for three years.
Second Date Update: Haunted House Hero
Brooke and Jeffrey feature a listener named Nathan who met Chloe at a haunted house after rescuing her from a panic attack.
FULL SHOW: Break Room Romeo Date, Jeff’s Busted Birthday + Brooke Goes to the Club (10/21/26)
Brooke and Jeffrey discuss Halloween participation rates by generation and play a trivia game about Kim Kardashian, Doja Cat, and Judge Judy.
Second Date Update Classics: Dutch Isn't Just A Language + Dry Lips & Hands On Hips
In this episode, Jake and Kim discuss their first date, where Kim discovered Jake’s Venmo history and interpreted it as him being a sugar daddy, leading her to decline a second date.
Second Date Update: Apple Picking For The 1 Percent
Brooke and Jeffrey interview Daniel, a retired "flavorist" who claims his wealthiness attracts only sugar babies, and Lily, who ghosted him after he…
Awkward Thursday: HOA Candy Crackdown
In this Awkward Thursday segment, David calls for help after his HOA mandates fun-size Halloween candy and threatens fines for handing out king-size bars.
Second Date Update: Microwaved Salad Guy
Brooke and Jeffrey discuss listener Eric’s awkward first date with his coworker Regina, which included an uninvited bra strap adjustment and an impromptu Uber ride where Eric shushed her.
Awkward Tuesday Phone Call: No No No Show
Catherine calls the show to confront her brother Warren, who no-showed her wedding and ignored her calls for two weeks.
Second Date Update: Food Court Cutie
Brooke and Jeffrey discuss listener Susan’s second date update, where she met a man named Tim at a mall food court and joined his friend group for drinks.
FULL SHOW: Jeff’s Ode to Pasta, Overly Romantic Date + Dumbest Healthcare Questions (10/16/26)
Hosts Brooke and Jeffrey discuss a listener named Kyle who flew a woman named Sandra out for their first in-person meeting after a month of online chatting.
Second Date Update Classics: Bathroom 911 + Big Fajita Energy
This episode features two "Second Date Update" segments.
Second Date Update: Vacation On Me
Listener Kyle shares his story of paying for a woman's flight and leaving 34 romantic notes in her hotel room, only for her to vanish without a word.
Second Date Update UPDATE: A Whole New Girlfriend
Brooke and Jeffrey revisit a listener who revealed he is a Disney adult on his first date, causing his match to lose interest.
Second Date Update: The Sobfather
Listener David shares his experience of crying three times on a first date with Shay, triggered by nostalgic salt and pepper shakers, her Las Vegas photos, and her kindness.
Awkward Tuesday: A Rabbi Walks Into A Bar
In this Awkward Tuesday episode, listener Simon seeks advice after a religious joke at a dinner party led his girlfriend’s parents to mistakenly believe he is Jewish.
Second Date Update: McLaren Missus Mishap
Evan, a luxury car salesman, takes his date Sarah to his McLaren dealership after hours to impress her, but she stops responding.
FULL SHOW: Bridezilla Closure Call, Thanksgiving Sabotage Secret + Hot Pocket Lie (10/8/26)
Brooke and Jeffrey discuss the new Avengers Dunkin' collaboration and play a taco-themed trivia game for National Taco Week.
Second Date Update Classics: Hotel Bar Rendezvous + Facebook KO
In this episode, Brooke and Jeffrey discuss two "Second Date Update" stories.
Second Date Update Classic: Burned By Beauties
Listener Riley shares his awkward first date with Dana, which began at an animal mask art event, but he is now being ghosted after reaching out to her ex for background checks.
Closure Call: Ex Best-Zila
Brooke and Jeffrey read a closure call from listener Gina, who was ghosted by her friend Catherine after a wedding six years ago.
Second Date Update: Dating Is Such A Chore
Mike called in to discuss a date with Chrissy, who claimed to be doing yard work but actually used him to make her ex-husband jealous.
FULL SHOW: Hots for My Uncle Update UPDATE, Kid’s Lunch Goldmine + 30 Year Secret (10/1/26)
Brooke and Jeffrey discuss Halloween costume trends and a listener’s confession about flooding his parents’ house during a Hawaii trip.
Second Date Update Classics: Mystery Treadmill Man + Till Date Do Us Part
Brooke and Jeffrey discuss two "Second Date Update" stories.
Second Date Update: G-Wagon Naggin'
Listener Hannah calls in to discuss her chaotic first date with Paul, who she claims is a great match despite their bickering.
Second Date Update UPDATE: Universe Is Busy Right Now
Allie claims she manifested a boyfriend by sketching him, but her date turned out to be Chris’s uncle, Phil, who was posing as Chris during their video chats.
Second Date Update: The Muffin Lady
Listener Vince seeks help after his dates with Jamie turn into bizarre car-based encounters where she drives him around and shoves muffins in his mouth.
Awkward Tuesday: House Guest's Fiancée
Rick returns to Awkward Tuesday to confess two major secrets to his fiancée: he has been unemployed for weeks and has a child from a past relationship.
Second Date Update: Third Wheel Steal
Nick calls in to explain how he accidentally crashed his brother Logan's date with Stephanie after Logan forgot the appointment.
FULL SHOW: Evict My House Guest Awkward, Whatcha Doin’ at Oktoberfest + Prison Prank (9/22/26)
Brooke and Jeffrey discuss the TSA's crackdown on squishy toys and play a Martian Mind Melter edition of Plenty of 20 focused on pop culture aliens.
Second Date Update Classics: Mothers Dayte + Terrible Tarot
Chris, a 32-year-old man, brings his overprotective mother to his date with Bella, causing her to feel awkward and refuse a second chance.
Second Date Update: Unwritten Rules For Fools
Brooke and Jeffrey discuss unwritten rules for overnight dates before interviewing listener Jack, who claims his date Sarah has been cold after he ate her chips.
Awkward Thursday: Hopsticle Course
In this Awkward Thursday segment, listener Caden seeks advice on convincing his coworker Violet to take him to the Bahamas after he faked an injury to let her enter an office competition.
Second Date Update: Drive Thru Date
In this "Second Date Update," listener Cody, 35, seeks help after a disastrous lunch date with Tiz, a barista 11 years his junior.
Awkward Tuesday: House Guest
Molly calls to discuss her college friend Rick, who has become an unwelcome houseguest by staying over frequently and asking for garage access.
Second Date Update: Bump Set Date
In this "Second Date Update," Tracy and Rob discuss their awkward connection after meeting at a beach volleyball game.
FULL SHOW: Pet Food Tasting Dare, Naughty Pumpkin Song + Bridesmaid Confession (9/17/26)
Brooke and Jeffrey host a special episode featuring a "Miss America" trivia game where the hosts and a guest answer questions about pageant history.