Brooke and Jeffrey: Second Date Update Classics

Episode: The Boy Who Cried Tree + Deck The Mall
Date: December 20, 2025
Podcast: Brooke and Jeffrey: Second Date Update
Host: iHeartPodcasts

Episode Overview

This episode features two classic, holiday-themed "Second Date Updates," where the Brooke and Jeffrey team attempts to solve listeners' awkward dating mysteries. Both segments highlight the hilarious, sometimes painful fallout that comes when a promising first date is followed by radio silence—and the show tries to uncover the truth behind the ghosting. The stories are filled with holiday mishaps, gift-giving snafus, and a reminder of how misunderstandings or misplaced expectations can turn a potential romance into a "never again."

Segment 1: The Boy Who Cried Tree

(Starts ~02:47)

Main Storyline

Brian returns as a repeat "Second Date Update" subject, seeking help after being ghosted post-date by Aubrey.
He reached out to Aubrey after seeing her in a coworker's Instagram photo, learning she'd be spending her first Christmas away from family.
To cheer her up, Brian invited her to a Christmas tree farm outing, hoping to make her season a little brighter.

Key Discussion Points & Insights

Brian and Aubrey both wore festive Christmas sweaters ("Jingle & Single" for him; hers said "Santa's favorite. Ho, ho, ho." 07:00).
They turned the outing into a mini celebration with some airplane bottles of whiskey to "loosen up" the mood.
They find the "perfect tree," but Brian is shocked by the price and hesitates; Aubrey offers to split the cost.
- Memorable moment (07:59):
  Brian: “She saw the look on my face when I saw that price tag and she was like, 'Alright, we're definitely splitting this.' Yeah, I was like, 'Yeah, we are.'”
Brian helps set up the tree at Aubrey’s place but doesn’t stay to decorate—she says she has dinner plans. Afterward, she stops responding to messages.

Notable Quotes & Humor

Brooke (about ghosting): “I feel like we cursed your love life and you're just stuck with us.” (04:54)
Brian: “Actually, I emailed all the other morning shows, but you're the only ones that responded.” (05:02)
The hosts tease Brian about making them “side characters” in his dating dramas and their low success rate:
“Well, we have very low standards here, so welcome back...” (05:08)

The Reveal – Why Aubrey Ghosted (13:10–19:23)

Aubrey explains she went back on the lot to look for a missing glove and encountered a six-year-old boy crying—he said Brian and Aubrey took the tree he was standing by and claimed as his own (14:03).
Aubrey confronts Brian, who refuses to take the tree down:
Aubrey: “There is a six year old little boy crying at Christmas time. Like, I don’t freaking care if you didn’t see him...”
Brian’s defense:
“Well, how did I cut one? I didn’t cut down the little boy's tree because he didn't pay for it.” (16:21) “Kids are standing next to every tree. So does that mean that's their tree too?” (16:52)
The debate escalates: Is it heartless to keep the tree, or was the dad using his son’s tears to avoid paying for an expensive tree?
Aubrey is turned off by Brian’s lack of holiday spirit and empathy:
Aubrey: “We had an opportunity to do something really kind for a child at Christmas... and you chose not to do it.” (18:12)

Classic Rejection & Aftermath

Hosts attempt a guilt trip:
“There is a sad boy on the other line who cannot get another date with a woman that he really likes. And all he wants for Christmas is one more date...” (18:39)
Aubrey declines:
Aubrey: “It's gonna be a hard pass.” (19:39)
Brian gamely sings Wham!:
Brian: “Last Christmas I gave you my heart, but the very next day you gave it away.” (20:02)
Brooke: “Now, now there's a whole studio full of sad radio hosts... Good job, Aubrey.” (19:45)
Aubrey: “I think there's a pattern here. Yeah, it's not me. It's Brian.” (19:55)

Segment Summary

The hosts reflect humorously afterward about "kids crying at the tree farm" (22:01) and debate whether kids’ reactions should dictate adult decisions:
Brooke: “Kids cry all the time… If we did everything based on what would upset a child, no one would do anything in this world.” (22:10)
Brian leaves still loveless, and the team is now "0 for 2" with his second date updates.

Segment 2: Deck The Mall

(Starts ~24:03)

Main Storyline

Para seeks help after being ghosted by Bryce, whom she met via office matchmaker Jana at a work holiday party.
Bryce invites Para to go Christmas shopping at the mall, which stretches into a five-hour marathon.
They browse for gifts for his family, look at "cute, sexy outfits" (which Bryce has her hold up to herself for jokes/flirting), and enjoy a meal in the food court.
At the end, Bryce says he’ll “circle back” with Jana and thank her, then disappears from communication. Jana also starts avoiding Para.

Key Discussion Points & Insights

Para shares how she misread the signals, thinking the marathon shopping trip was fun and flirty.
The hosts wonder: is it a real date, or did Bryce have ulterior motives?

Notable Quotes & Humor

Alexis: “This is like a 1996 date all over again.” (28:03)
Para (on Bryce’s weird closing comment): “He said he was going to circle back with Jana and thank her for introducing us... It comes off so businesslike.”
The panel jokes about office matchmakers, questionable Secret Santa arrangements, and the misery of five hours at the mall.

The Reveal – Why Bryce Ghosted (32:04–39:08)

When contacted, Bryce is surprised by the call and says flatly he’s not interested:
“I got all my Christmas shopping done. That was cool. She was really helpful.” (33:00)
Bryce admits: He has a girlfriend (Helen), and Jana recommended Para as a great "personal shopper" because she always gave great Secret Santa gifts. He assumed Para understood the arrangement.
Para is shocked—it wasn’t made clear, and all her signals were missed. The "flirting" was, in her mind, real.
The money for her time: Bryce supposedly gave Jana $50 to "pass on" to Para for her time; Para never got it.
Para calls this "sketchy" and feels used; host Alexis points out, “Jana is the scandalous one!” (37:24)
Bryce admits he probably should have been clearer and chalks the debacle up to miscommunication but offers no real apology.

Classic Rejection & Aftermath

Para: “No chance,” on a future date, but jokes she’ll help him shop "as long as we’re very clear that’s what it is.” (39:14)
Hosts riff on the bathrobe shopping and “old lady” names and even poke fun at Bryce’s cluelessness and Helen’s possible reaction.

Notable Quotes, Banter & Memorable Moments

Brian (when pressed about other morning shows):
“Actually, I emailed all of them, but you’re the only ones that responded.” (05:02)
On holiday tree pricing:
Brian: "It was like in three figures. It was pretty high." (07:38)
Aubrey: “We had an opportunity to do something really kind for a child at Christmas time, and you chose not to do it.” (18:12)
On the shopping date:
Para: "We did look at some really cute, sexy outfits, but he had me put them up to me and, you know, he complimented me...” (27:04)
Bryce (on the supposed payment):
“I actually gave some money to Jana that I intended her to give to Para...” (34:04)
Alexis concludes: “Jana’s the scandalous one!”

Timestamps for Key Segments

Brian checks in for another second date update: 04:20
Brian recounts Christmas tree farm date: 05:16–09:00
Aubrey describes the “tree stealing” story: 13:16–15:33
On-air confrontation/reveal between Brian and Aubrey: 16:17–19:23
Post-segment discussion/jokes: 22:01
Para introduces her office holiday ghost story: 25:06
Para’s account of the shopping date: 26:22–28:10
Bryce's side and the big misunderstanding: 33:00–38:01
Host analysis and banter at close: 41:12

Episode Tone and Takeaways

Fast-paced, irreverent, filled with playful teasing—especially around holiday traditions and mishaps.
Both segments hinge on major miscommunication and holiday stress amplifying dating awkwardness.
The hosts lean into the ridiculousness and frustration, but also reflect on dating etiquette, kindness, and the unpredictability of romance during the holidays.

For New Listeners

This episode showcases the best of Brooke and Jeffrey’s holiday cringe. Whether it’s fighting over a Christmas tree with a sobbing child or serving as an unpaid “personal shopper,” the pain of modern dating is real—but at least it makes for some hilarious radio, and maybe a few lessons for future holiday daters.

Brooke and Jeffrey: Second Date Update Classics

Episode: The Boy Who Cried Tree + Deck The Mall
Date: December 20, 2025
Podcast: Brooke and Jeffrey: Second Date Update
Host: iHeartPodcasts

Episode Overview

Segment 1: The Boy Who Cried Tree

(Starts ~02:47)

Main Storyline

Brian returns as a repeat "Second Date Update" subject, seeking help after being ghosted post-date by Aubrey.
He reached out to Aubrey after seeing her in a coworker's Instagram photo, learning she'd be spending her first Christmas away from family.
To cheer her up, Brian invited her to a Christmas tree farm outing, hoping to make her season a little brighter.

Key Discussion Points & Insights

Brian and Aubrey both wore festive Christmas sweaters ("Jingle & Single" for him; hers said "Santa's favorite. Ho, ho, ho." 07:00).
They turned the outing into a mini celebration with some airplane bottles of whiskey to "loosen up" the mood.
They find the "perfect tree," but Brian is shocked by the price and hesitates; Aubrey offers to split the cost.
- Memorable moment (07:59):
  Brian: “She saw the look on my face when I saw that price tag and she was like, 'Alright, we're definitely splitting this.' Yeah, I was like, 'Yeah, we are.'”
Brian helps set up the tree at Aubrey’s place but doesn’t stay to decorate—she says she has dinner plans. Afterward, she stops responding to messages.

Notable Quotes & Humor

Brooke (about ghosting): “I feel like we cursed your love life and you're just stuck with us.” (04:54)
Brian: “Actually, I emailed all the other morning shows, but you're the only ones that responded.” (05:02)
The hosts tease Brian about making them “side characters” in his dating dramas and their low success rate:
“Well, we have very low standards here, so welcome back...” (05:08)

The Reveal – Why Aubrey Ghosted (13:10–19:23)

Aubrey explains she went back on the lot to look for a missing glove and encountered a six-year-old boy crying—he said Brian and Aubrey took the tree he was standing by and claimed as his own (14:03).
Aubrey confronts Brian, who refuses to take the tree down:
Aubrey: “There is a six year old little boy crying at Christmas time. Like, I don’t freaking care if you didn’t see him...”
Brian’s defense:
“Well, how did I cut one? I didn’t cut down the little boy's tree because he didn't pay for it.” (16:21) “Kids are standing next to every tree. So does that mean that's their tree too?” (16:52)
The debate escalates: Is it heartless to keep the tree, or was the dad using his son’s tears to avoid paying for an expensive tree?
Aubrey is turned off by Brian’s lack of holiday spirit and empathy:
Aubrey: “We had an opportunity to do something really kind for a child at Christmas... and you chose not to do it.” (18:12)

Classic Rejection & Aftermath

Hosts attempt a guilt trip:
“There is a sad boy on the other line who cannot get another date with a woman that he really likes. And all he wants for Christmas is one more date...” (18:39)
Aubrey declines:
Aubrey: “It's gonna be a hard pass.” (19:39)
Brian gamely sings Wham!:
Brian: “Last Christmas I gave you my heart, but the very next day you gave it away.” (20:02)
Brooke: “Now, now there's a whole studio full of sad radio hosts... Good job, Aubrey.” (19:45)
Aubrey: “I think there's a pattern here. Yeah, it's not me. It's Brian.” (19:55)

Segment Summary

The hosts reflect humorously afterward about "kids crying at the tree farm" (22:01) and debate whether kids’ reactions should dictate adult decisions:
Brooke: “Kids cry all the time… If we did everything based on what would upset a child, no one would do anything in this world.” (22:10)
Brian leaves still loveless, and the team is now "0 for 2" with his second date updates.

Segment 2: Deck The Mall

(Starts ~24:03)

Main Storyline

Para seeks help after being ghosted by Bryce, whom she met via office matchmaker Jana at a work holiday party.
Bryce invites Para to go Christmas shopping at the mall, which stretches into a five-hour marathon.
They browse for gifts for his family, look at "cute, sexy outfits" (which Bryce has her hold up to herself for jokes/flirting), and enjoy a meal in the food court.
At the end, Bryce says he’ll “circle back” with Jana and thank her, then disappears from communication. Jana also starts avoiding Para.

Key Discussion Points & Insights

Para shares how she misread the signals, thinking the marathon shopping trip was fun and flirty.
The hosts wonder: is it a real date, or did Bryce have ulterior motives?

Notable Quotes & Humor

Alexis: “This is like a 1996 date all over again.” (28:03)
Para (on Bryce’s weird closing comment): “He said he was going to circle back with Jana and thank her for introducing us... It comes off so businesslike.”
The panel jokes about office matchmakers, questionable Secret Santa arrangements, and the misery of five hours at the mall.

The Reveal – Why Bryce Ghosted (32:04–39:08)

When contacted, Bryce is surprised by the call and says flatly he’s not interested:
“I got all my Christmas shopping done. That was cool. She was really helpful.” (33:00)
Bryce admits: He has a girlfriend (Helen), and Jana recommended Para as a great "personal shopper" because she always gave great Secret Santa gifts. He assumed Para understood the arrangement.
Para is shocked—it wasn’t made clear, and all her signals were missed. The "flirting" was, in her mind, real.
The money for her time: Bryce supposedly gave Jana $50 to "pass on" to Para for her time; Para never got it.
Para calls this "sketchy" and feels used; host Alexis points out, “Jana is the scandalous one!” (37:24)
Bryce admits he probably should have been clearer and chalks the debacle up to miscommunication but offers no real apology.

Classic Rejection & Aftermath

Para: “No chance,” on a future date, but jokes she’ll help him shop "as long as we’re very clear that’s what it is.” (39:14)
Hosts riff on the bathrobe shopping and “old lady” names and even poke fun at Bryce’s cluelessness and Helen’s possible reaction.

Notable Quotes, Banter & Memorable Moments

Brian (when pressed about other morning shows):
“Actually, I emailed all of them, but you’re the only ones that responded.” (05:02)
On holiday tree pricing:
Brian: "It was like in three figures. It was pretty high." (07:38)
Aubrey: “We had an opportunity to do something really kind for a child at Christmas time, and you chose not to do it.” (18:12)
On the shopping date:
Para: "We did look at some really cute, sexy outfits, but he had me put them up to me and, you know, he complimented me...” (27:04)
Bryce (on the supposed payment):
“I actually gave some money to Jana that I intended her to give to Para...” (34:04)
Alexis concludes: “Jana’s the scandalous one!”

Timestamps for Key Segments

Brian checks in for another second date update: 04:20
Brian recounts Christmas tree farm date: 05:16–09:00
Aubrey describes the “tree stealing” story: 13:16–15:33
On-air confrontation/reveal between Brian and Aubrey: 16:17–19:23
Post-segment discussion/jokes: 22:01
Para introduces her office holiday ghost story: 25:06
Para’s account of the shopping date: 26:22–28:10
Bryce's side and the big misunderstanding: 33:00–38:01
Host analysis and banter at close: 41:12

Episode Tone and Takeaways

Fast-paced, irreverent, filled with playful teasing—especially around holiday traditions and mishaps.
Both segments hinge on major miscommunication and holiday stress amplifying dating awkwardness.
The hosts lean into the ridiculousness and frustration, but also reflect on dating etiquette, kindness, and the unpredictability of romance during the holidays.

Second Date Update Classics: The Boy Who Cried Tree + Deck The Mall

Summary

Brooke and Jeffrey: Second Date Update Classics

Episode Overview

Segment 1: The Boy Who Cried Tree

(Starts ~02:47)

Main Storyline

Key Discussion Points & Insights

Notable Quotes & Humor

The Reveal – Why Aubrey Ghosted (13:10–19:23)

Classic Rejection & Aftermath

Segment Summary

Segment 2: Deck The Mall

(Starts ~24:03)

Main Storyline

Key Discussion Points & Insights

Notable Quotes & Humor

The Reveal – Why Bryce Ghosted (32:04–39:08)

Classic Rejection & Aftermath

Notable Quotes, Banter & Memorable Moments

Timestamps for Key Segments

Episode Tone and Takeaways

For New Listeners

Summary

Brooke and Jeffrey: Second Date Update Classics

Episode Overview

Segment 1: The Boy Who Cried Tree

(Starts ~02:47)

Main Storyline

Key Discussion Points & Insights

Notable Quotes & Humor

The Reveal – Why Aubrey Ghosted (13:10–19:23)

Classic Rejection & Aftermath

Segment Summary

Segment 2: Deck The Mall

(Starts ~24:03)

Main Storyline

Key Discussion Points & Insights

Notable Quotes & Humor

The Reveal – Why Bryce Ghosted (32:04–39:08)

Classic Rejection & Aftermath

Notable Quotes, Banter & Memorable Moments

Timestamps for Key Segments

Episode Tone and Takeaways

For New Listeners