Brooke and Jeffrey: Second Date Update

Episode: "Top 10 Loser Lines of 2025" (November 20, 2025)

Hosted by: Brooke, Jeffrey, and Producer Boy
Podcast Theme: A hilarious annual countdown of the weirdest, cringiest, and most memorable prank voicemails left on the show's famous "Loser Line"—a fake phone number listeners hand out to would-be suitors.

Episode Overview

This episode delivers a riotous highlight reel of the year’s ten best "Loser Line" voicemails, chosen from hundreds of prank calls, nervous confessions, accidental overshares, and bizarre creative performances. The hosts, in classic playful style, banter over the clips—giving listeners awkward, earnest, and absurd real-life moments from modern dating. The entire countdown is packed with cringe, humor, and the strong personalities of the hosts.

Key Segments & Highlights

1. The Loser Line Explained & Year-in-Review Banter

[03:05 – 05:33]
- The hosts explain the concept: for over a decade, they've handed out a fake "Loser Line" number, which goes viral every year. Callers leave messages not realizing they've been gently rebuffed.
- Brooke: "We combed through them all, selected our top 10 favorite ones. We're gonna play ‘em for you next."
- Hosts joke about this crazy year: TikTok’s shutdown and relaunch, Katy Perry’s emotional space trip, and Coldplay concerts as affairs hot spots.
- Jeffrey: "Maybe the craziest thing, though, is we are still on the air. How did that happen?" ([05:33])

2. The Top 10 Countdown

#10: Shower Multitasking Guy

[06:05 – 06:56]
- Caller nonchalantly leaves a voicemail from the shower: “Tried this a few months ago, where lately I’ve been trying to multitask...you just happened to fall on shower time, so. Lucky you.”
- Wild invention ideas: USB toasters for the car, glove-compartment hot plates for breakfast.
- Quote: “Did you know you can buy one of those wireless USB toasters where you can actually toast in your car? ...I should probably go, the water is getting cold.” — Shower Guy ([06:05])
- Host reactions:
  - Producer Boy: "I'm just glad that he combined his toaster with his car and not with a shower."
  - Jeffrey: “If anybody will find a way, this guy will.”

#9: The "Ice Ice Baby" Rap

[07:25 – 08:09]
- Awkward suitor remixes "Ice Ice Baby" to ask someone out.
- Quote: "Ask, ask baby. Will you go? Will you go out? Will you go, Please, please date me? Come on, girl." — Rap Guy ([07:25])
- Hosts: Brooke dances along, Producer Boy reminisces fondly/awkwardly about goofy voicemail greetings.

#8: The Over-Involved Daughter

[08:29 – 09:20]
- Woman calls to warn off a date from her mom, whom she’s trying to reunite with her estranged, possibly confused, bio dad.
- Quote: “I really just need you to back off.” — Interfering Daughter ([08:29])
- Hosts: Laugh about family drama being used as a Loser Line handoff.

#7: Tea Spill Professional

[09:39 – 10:29]
- Voicemail capturing a real-life disaster: a woman scalds herself with tea, curses coffee cups, and prepares for a Zoom call.
- Quote: “Stupid pants. Come on. Forget it. It’s just. It’s not working. I’m just gonna have to change pants.” — Flustered Woman ([09:39])
- Hosts: Reminisce about the original idea of the Loser Line and how it's now given to coworkers and family.

#6: The Slice Guy (Pepperoni Suitor)

[11:06 – 11:55]
- Young man (in a pepperoni costume) flirts, apologizes for his “stay cheesy” line, and awkwardly assures the recipient he is 18 and “legal.”
- Quote: “Sometimes people can’t tell from the costume. But I’m legal.” — Slice Guy ([11:06])
- Host reactions: Producer Boy: “I don’t like that. That is…”; Jeffrey jokes about awkwardness and young sign spinners.

[MID-COUNTDOWN BANter & Recap]

[12:13 – 13:19]
- Recap the ridiculousness so far: showers, tea spills, pizza slices, and universal cringe.

#5: Corn Council Auditioner

[13:34 – 14:38]
- Caller auditions to be the phone voice for the "county corn council," improvising on the spot: “To report a corn related emergency, press 1... To speak with a certified corn representative, press 4. Have a corn-tastic day.”
- Quote: “Thank you for calling the county corn council where corn is our passion…” — Corn Council Guy ([13:34])
- Host reaction: “Hire him!” They laugh at the detailed corn hotline menu.

#4: The Abstinence Loophole Guy

[15:05 – 16:06]
- Man (abstinence seminar speaker) awkwardly flirts, hinting he knows “workarounds” to abstinence, and overshares his expert status.
- Quote: “I know it’s probably weird that the abstinence guy is asking you out, but let’s just say there’s ways to get around all that, if you know what I mean.” — Abstinence Loophole Guy ([15:05])
- Hosts: Producer Boy: “Why are the abstinence loophole people always the one that are the creepiest?” Jeffrey: “Just don’t do it."

#3: The Fungal Bloom Oversharer

[16:36 – 17:39]
- Excruciatingly candid message about a neck rash: “...doctor said it’s just a heat induced fungal bloom...wasn’t as bad as the ringworm I caught last summer…Don’t drink expired kombucha.”
- Quote: “Let’s put the fun in fungal.” — Fungal Bloom Guy ([16:36])
- Hosts: Jeffrey: “No one has ever hooked up after saying fungal bloom.”

#2: Pirate Accent Date Request

[18:06 – 18:50]
- Suitor puts on an elaborate pirate accent, asking Shelley to “sail the seven seas,” hoping the accent will help: “Maybe we can see something that’s rated Arrrrr.”
- Quote: “Gar, I know you’ve never heard this voice before, but I had a wheeled talk with your friend before I left the bar…” — Pirate Logan ([18:06])
- Hosts: Joke about pirate hygiene, "Pirate mouth," and talk up pirate date possibilities.

#1: The Great Alfonso, Off-Duty Birthday Magician

[19:28 – 20:46]
- Magician calls after a kids' birthday gig; thanks recipient for not telling host mom about his flask. Compliments their realness: “…right around when I did the foam rabbit popping out of the Pringles can.”
- Ends with: “If you really want to party, I know a guy that can hook us up with...party favors.”
- Quote: “You just seemed like someone who’s seen some sh—before. You seemed real. Not like the bubble gum heads in the cloud. Life is rainbows and bullshit you hear from some of these moms.” — The Great Alfonso ([19:28])
- Hosts:
  - Producer Boy: “She missed out. Alfonso will deliver some stories.”
  - Jeffrey: “Don’t worry, I saved his number for our end of the year party.”
  - Brooke: “My favorite part is him being like, ‘Dude, she caught me with a flask. But she’s the crazy one.’”

Notable Quotes & Memorable Moments

On the evolution of the Loser Line:
- “Now it’s morphed into this whole new thing, and people are giving it to their quirky coworkers or their strange aunt or if you hit a parked car. It’s really come a long, long way since we first started.” — Jeffrey ([10:30])
On oversharers and cringe:
- “No one has ever hooked up after saying fungal bloom.” — Jeffrey ([17:39])
On youthful awkwardness:
- “That was his first job. Yeah, like a sign spinner...I think that was his first interaction with an adult.” — Producer Boy ([12:03])

Structure & Flow

Opening: Hosts set the mood in faux-fancy style, playful sarcasm, and self-aware banter about their “decorum.”
Countdown: Each segment features a voicemail followed by lively reactions, jokes, and commentary from Brooke, Jeffrey, and Producer Boy.
Host Chemistry: Frequent, natural interplay; blend of supportive teasing and shared laughter—adds charm and context to each message.
Closure: After the #1 message, the hosts tie it together with shoutouts to socials and future hopes for more entertaining Loser Line content.

Timestamps for Important Segments

| Segment | Timestamp | | --------------- | --------- | | Loser Line intro & year-in-review banter | [03:05 – 05:33] | | #10: Shower Multitasking Guy | [06:05 – 06:56] | | #9: “Ice Ice Baby” Rap | [07:25 – 08:09] | | #8: Daughter-blocks-Mom’s Date | [08:29 – 09:20] | | #7: Tea Spill Zoom Disaster | [09:39 – 10:29] | | #6: Slice Guy (Pepperoni Suit) | [11:06 – 11:55] | | Mid-countdown Recap & Banter | [12:13 – 13:19] | | #5: County Corn Council Audition | [13:34 – 14:38] | | #4: Abstinence Loophole Guy | [15:05 – 16:06] | | #3: Fungal Bloom Oversharer | [16:36 – 17:39] | | #2: Pirate Accent Date Request | [18:06 – 18:50] | | #1: The Great Alfonso | [19:28 – 20:46] |

Final Thoughts

“Top 10 Loser Lines of 2025” is a comedic highlight reel, showcasing the social awkwardness, creativity, oversharing, and surprising sincerity of modern dating fails. The hosts’ irreverent, supportive energy—combined with off-the-wall callers—makes for a high-entertainment, low-success matchmaking experience, to the joy of listeners everywhere.

For those seeking awkward laughs, a peek at dating disasters, or simply some inventive ways to avoid uncomfortable encounters, this annual countdown is a must-listen.

Brooke and Jeffrey: Second Date Update

Episode: "Top 10 Loser Lines of 2025" (November 20, 2025)

Episode Overview

Key Segments & Highlights

1. The Loser Line Explained & Year-in-Review Banter

[03:05 – 05:33]
- The hosts explain the concept: for over a decade, they've handed out a fake "Loser Line" number, which goes viral every year. Callers leave messages not realizing they've been gently rebuffed.
- Brooke: "We combed through them all, selected our top 10 favorite ones. We're gonna play ‘em for you next."
- Hosts joke about this crazy year: TikTok’s shutdown and relaunch, Katy Perry’s emotional space trip, and Coldplay concerts as affairs hot spots.
- Jeffrey: "Maybe the craziest thing, though, is we are still on the air. How did that happen?" ([05:33])

2. The Top 10 Countdown

#10: Shower Multitasking Guy

[06:05 – 06:56]
- Caller nonchalantly leaves a voicemail from the shower: “Tried this a few months ago, where lately I’ve been trying to multitask...you just happened to fall on shower time, so. Lucky you.”
- Wild invention ideas: USB toasters for the car, glove-compartment hot plates for breakfast.
- Quote: “Did you know you can buy one of those wireless USB toasters where you can actually toast in your car? ...I should probably go, the water is getting cold.” — Shower Guy ([06:05])
- Host reactions:
  - Producer Boy: "I'm just glad that he combined his toaster with his car and not with a shower."
  - Jeffrey: “If anybody will find a way, this guy will.”

#9: The "Ice Ice Baby" Rap

[07:25 – 08:09]
- Awkward suitor remixes "Ice Ice Baby" to ask someone out.
- Quote: "Ask, ask baby. Will you go? Will you go out? Will you go, Please, please date me? Come on, girl." — Rap Guy ([07:25])
- Hosts: Brooke dances along, Producer Boy reminisces fondly/awkwardly about goofy voicemail greetings.

#8: The Over-Involved Daughter

[08:29 – 09:20]
- Woman calls to warn off a date from her mom, whom she’s trying to reunite with her estranged, possibly confused, bio dad.
- Quote: “I really just need you to back off.” — Interfering Daughter ([08:29])
- Hosts: Laugh about family drama being used as a Loser Line handoff.

#7: Tea Spill Professional

[09:39 – 10:29]
- Voicemail capturing a real-life disaster: a woman scalds herself with tea, curses coffee cups, and prepares for a Zoom call.
- Quote: “Stupid pants. Come on. Forget it. It’s just. It’s not working. I’m just gonna have to change pants.” — Flustered Woman ([09:39])
- Hosts: Reminisce about the original idea of the Loser Line and how it's now given to coworkers and family.

#6: The Slice Guy (Pepperoni Suitor)

[11:06 – 11:55]
- Young man (in a pepperoni costume) flirts, apologizes for his “stay cheesy” line, and awkwardly assures the recipient he is 18 and “legal.”
- Quote: “Sometimes people can’t tell from the costume. But I’m legal.” — Slice Guy ([11:06])
- Host reactions: Producer Boy: “I don’t like that. That is…”; Jeffrey jokes about awkwardness and young sign spinners.

[MID-COUNTDOWN BANter & Recap]

[12:13 – 13:19]
- Recap the ridiculousness so far: showers, tea spills, pizza slices, and universal cringe.

#5: Corn Council Auditioner

[13:34 – 14:38]
- Caller auditions to be the phone voice for the "county corn council," improvising on the spot: “To report a corn related emergency, press 1... To speak with a certified corn representative, press 4. Have a corn-tastic day.”
- Quote: “Thank you for calling the county corn council where corn is our passion…” — Corn Council Guy ([13:34])
- Host reaction: “Hire him!” They laugh at the detailed corn hotline menu.

#4: The Abstinence Loophole Guy

[15:05 – 16:06]
- Man (abstinence seminar speaker) awkwardly flirts, hinting he knows “workarounds” to abstinence, and overshares his expert status.
- Quote: “I know it’s probably weird that the abstinence guy is asking you out, but let’s just say there’s ways to get around all that, if you know what I mean.” — Abstinence Loophole Guy ([15:05])
- Hosts: Producer Boy: “Why are the abstinence loophole people always the one that are the creepiest?” Jeffrey: “Just don’t do it."

#3: The Fungal Bloom Oversharer

[16:36 – 17:39]
- Excruciatingly candid message about a neck rash: “...doctor said it’s just a heat induced fungal bloom...wasn’t as bad as the ringworm I caught last summer…Don’t drink expired kombucha.”
- Quote: “Let’s put the fun in fungal.” — Fungal Bloom Guy ([16:36])
- Hosts: Jeffrey: “No one has ever hooked up after saying fungal bloom.”

#2: Pirate Accent Date Request

[18:06 – 18:50]
- Suitor puts on an elaborate pirate accent, asking Shelley to “sail the seven seas,” hoping the accent will help: “Maybe we can see something that’s rated Arrrrr.”
- Quote: “Gar, I know you’ve never heard this voice before, but I had a wheeled talk with your friend before I left the bar…” — Pirate Logan ([18:06])
- Hosts: Joke about pirate hygiene, "Pirate mouth," and talk up pirate date possibilities.

#1: The Great Alfonso, Off-Duty Birthday Magician

[19:28 – 20:46]
- Magician calls after a kids' birthday gig; thanks recipient for not telling host mom about his flask. Compliments their realness: “…right around when I did the foam rabbit popping out of the Pringles can.”
- Ends with: “If you really want to party, I know a guy that can hook us up with...party favors.”
- Quote: “You just seemed like someone who’s seen some sh—before. You seemed real. Not like the bubble gum heads in the cloud. Life is rainbows and bullshit you hear from some of these moms.” — The Great Alfonso ([19:28])
- Hosts:
  - Producer Boy: “She missed out. Alfonso will deliver some stories.”
  - Jeffrey: “Don’t worry, I saved his number for our end of the year party.”
  - Brooke: “My favorite part is him being like, ‘Dude, she caught me with a flask. But she’s the crazy one.’”

Notable Quotes & Memorable Moments

On the evolution of the Loser Line:
- “Now it’s morphed into this whole new thing, and people are giving it to their quirky coworkers or their strange aunt or if you hit a parked car. It’s really come a long, long way since we first started.” — Jeffrey ([10:30])
On oversharers and cringe:
- “No one has ever hooked up after saying fungal bloom.” — Jeffrey ([17:39])
On youthful awkwardness:
- “That was his first job. Yeah, like a sign spinner...I think that was his first interaction with an adult.” — Producer Boy ([12:03])

Structure & Flow

Opening: Hosts set the mood in faux-fancy style, playful sarcasm, and self-aware banter about their “decorum.”
Countdown: Each segment features a voicemail followed by lively reactions, jokes, and commentary from Brooke, Jeffrey, and Producer Boy.
Host Chemistry: Frequent, natural interplay; blend of supportive teasing and shared laughter—adds charm and context to each message.
Closure: After the #1 message, the hosts tie it together with shoutouts to socials and future hopes for more entertaining Loser Line content.

Timestamps for Important Segments

Final Thoughts

For those seeking awkward laughs, a peek at dating disasters, or simply some inventive ways to avoid uncomfortable encounters, this annual countdown is a must-listen.

Top 10 Loser Lines of 2025

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Summary

Brooke and Jeffrey: Second Date Update

Episode: "Top 10 Loser Lines of 2025" (November 20, 2025)

Episode Overview

Key Segments & Highlights

1. The Loser Line Explained & Year-in-Review Banter

2. The Top 10 Countdown

#10: Shower Multitasking Guy

#9: The "Ice Ice Baby" Rap

#8: The Over-Involved Daughter

#7: Tea Spill Professional

#6: The Slice Guy (Pepperoni Suitor)

[MID-COUNTDOWN BANter & Recap]

#5: Corn Council Auditioner

#4: The Abstinence Loophole Guy

#3: The Fungal Bloom Oversharer

#2: Pirate Accent Date Request

#1: The Great Alfonso, Off-Duty Birthday Magician

Notable Quotes & Memorable Moments

Structure & Flow

Timestamps for Important Segments

Final Thoughts

Summary

Brooke and Jeffrey: Second Date Update

Episode: "Top 10 Loser Lines of 2025" (November 20, 2025)

Episode Overview

Key Segments & Highlights

1. The Loser Line Explained & Year-in-Review Banter

2. The Top 10 Countdown

#10: Shower Multitasking Guy

#9: The "Ice Ice Baby" Rap

#8: The Over-Involved Daughter

#7: Tea Spill Professional

#6: The Slice Guy (Pepperoni Suitor)

[MID-COUNTDOWN BANter & Recap]

#5: Corn Council Auditioner

#4: The Abstinence Loophole Guy

#3: The Fungal Bloom Oversharer

#2: Pirate Accent Date Request

#1: The Great Alfonso, Off-Duty Birthday Magician

Notable Quotes & Memorable Moments

Structure & Flow

Timestamps for Important Segments

Final Thoughts