Brooke and Jeffrey: Second Date Update
Awkward Tuesday: Future Father In-Law
Podcast Date: September 2, 2025
Episode Overview
In this “Awkward Tuesday” edition of Brooke and Jeffrey: Second Date Update, the hosts help Garrett, a nervous boyfriend hoping to propose to his girlfriend Sienna. The catch? He must first earn the blessing of her intimidating, old-school father—a man infamous for denying previous requests from Sienna's ex-boyfriends, with rumors of bizarre, bear-related hypothetical questions. The crew coaches Garrett through an anxiety-ridden call, guiding him step-by-step to a surprisingly heartwarming conclusion.
Key Discussion Points & Insights
1. Garrett’s Dilemma: Winning Over the "Scary" Future Father-in-law
- Garrett introduces his situation: He wants to propose to Sienna after almost two years of dating but feels compelled to honor her family’s tradition by seeking her dad’s blessing.
- “She comes from a very traditional family where they expect you to kind of ask the dad's permission.” (07:02 – Garrett)
- Her dad’s history: Sienna’s previous boyfriends “failed” this test—her dad said no twice before, and both relationships ended.
- Host empathy: Brooke and Jose admit they’d feel pressure too; Jeffrey tries to normalize the nerves.
- “I think it’s natural for a lot of guys to be nervous about talking to the dad about this subject.” (07:44 – Jeffrey)
2. The Mysterious Bear Hypotheticals
- Garrett shares that Sienna warned him about her father’s hypothetical questions, supposedly about bears, often the downfall of past suitors.
- The crew jokes about all the possible “bear scenarios” Garrett could face, offering some half-serious survival advice.
- “Brown lie down. Black fight back. White, good luck.” (09:51 – Brooke)
3. Coaching Garrett: Advice From the Hosts
- Brooke’s advice: Focus on listening, not over-talking, and compliment the dad. Maybe ask about his “glory days”—dads love that.
- “These type of guys love for that.” (13:15 – Brooke)
- Jose’s advice: Try dad jokes as an icebreaker, but mainly, show respect (use his last name).
- Jeffrey’s support: Encourages confidence, frames the call as a bonding opportunity, not a confrontation.
- “Don’t think of him as your scary father-in-law. This is gonna be, like, your best bud.” (14:22 – Jeffrey)
The Phone Call: Garrett Dials Larry
Setup (14:44)
Garrett, with the group’s encouragement, nervously dials Sienna’s father, Larry. The interaction is immediately awkward:
Memorable Exchange:
- Larry: “Just don’t call me mister, just call me Larry.” (15:02)
- Garrett: “But I mean, I’m just trying to show respect. It’s important.”
- Larry: “Calling me Mr. Grove makes me seem like an old. So I don’t need that. Just, just call me Larry.”
The Permission Request (15:20 – 17:16)
- Garrett stumbles through small talk and finally states his intention:
“I’d really love to kind of take our relationship to the next step.”- Larry immediately asks a hypothetical—not about bears, but about Sienna being treated unfairly at work. Garrett, confused, tries to steer back to the bear scenario.
- Larry reveals the truth:
“Sienna just said that the two guys before me... both of them failed the question about bears.”
“Look, I’m pretty sure she’s just screwing with you.” (17:14 – Larry)
The Real Story (17:18 – 17:51)
- Larry clarifies the reasons he denied the previous suitors:
- “The first guy... I said no because he was a damn mouth breather.”
- “The second one, he was one of them pony boys... He kept wanting me to call him Applejack.”
- “That is a My Little Pony name, though.” (17:51 – Jose)
Intervention & Resolution
The hosts then reveal themselves, putting Larry at ease and explaining Garrett’s anxious preparation.
- Larry sizes up Garrett, pokes gentle fun (calling him “skittish”), but ultimately gives his approval:
- “Quite honestly, you’re the only normal one she’s ever brought around.” (19:59 – Larry)
- Larry can’t resist one more joke:
“If you come home from work and there’s a bear in the house, what are you gonna do?” (20:01 – Larry)
Everyone laughs; the tension breaks. - Garrett, prodded by Jose, tries the earlier dad joke:
- “What’s the difference between a hippo and a Zippo? One’s really heavy, and the other’s a little lighter.”
- Laughter ensues, and all agree upon Garrett’s suitability.
Notable Quotes & Memorable Moments
- Brooke on tradition:
“My husband didn’t do this. And it still kind of irks me to this day.” (07:02) - Jose on breakups:
“Did the dad say no—then you can't marry the daughter, right?” (07:53) - Larry’s real reasoning:
“The first guy... was a mouth breather. The second one... wanted me to call him Applejack.” (17:16-17:51) - On Sienna’s bear prank:
“Sienna just said that the two guys before me who... both of them failed the question about bears. Look, I’m pretty sure she’s just screwing with you.” (17:14 – Larry) - Jose, on the dad joke:
“You might as well check this box off.” (19:13) - Larry’s approval:
“You’re the only normal one she’s ever brought around.” (19:59) - Brooke, post-call:
“That was actually really cute. Larry was rad.” (22:38)
Important Timestamps
- Podcast proper begins: [03:06]
- Garrett introduces his dilemma: [06:01]
- Bear hypothetical discussed: [09:19], [12:40]
- Hosts give advice: [12:53 – 14:12]
- Garrett’s call to Larry starts: [14:44]
- Larry reveals real reasons for previous 'no's: [17:18]
- Lighthearted bear question/approval given: [20:01 – 20:35]
- Post-call reactions and wrap-up: [22:34]
Recap & Takeaways
This episode delivered trademark awkward comedy and sweet payoff, blending real relationship anxiety with quirky family traditions. The dad’s gruff exterior was tempered by humor and candidness, deflating years of myth about his infamous “bear questions.” In the end, Garrett’s genuine respect (and a last-minute dad joke) won him a rare “yes”—and listeners got one of the more wholesome, surprisingly funny calls in the show’s history.