Podcast Summary: Brooke and Jeffrey – Second Date Update: Unattractive Trey Is Back
Original Release: February 6, 2026
Hosts: Brooke, Jeffrey, Alexis, Bowen Yang
Episode Theme:
Trey, a fan-favorite recurring guest known for his dating mishaps and self-deprecating humor about his looks, returns for another "Second Date Update". After his previous date ghosted him (despite saying yes on air), Trey seeks help reconnecting with Julie—a woman he recently met while helping a stranded bus. The episode dives into Trey's persistent optimism, the unpredictable reality of modern dating, and the surprising, complicated reason for Julie's lack of contact.
Main Topics & Episode Flow
1. Trey’s Heartbreak Recap and Return
(04:38–06:28)
- The hosts reminisce about Trey's last appearance, recounting how he was insulted at a singles mixer and went out with a woman who turned out to be a paid attendee.
- “He’s been roasted, called ugly, then learned that the women at the event didn’t even want to be there.” – Jeffrey [05:10]
- Trey optimistically returns for another chance at love.
- “I’m giving love a chance. I’m hopeful.” – Trey [06:44]
2. How Trey Met Julie: The Broken-Down Bus Story
(06:44–09:14)
- Trey describes witnessing a broken-down bus on his way home and choosing to stop and help.
- “Not a lot of people would slow down at all, let alone stop to try and assist.” – Jeffrey [07:21]
- While helping, Trey chats with Julie, a fellow dog owner. They bond over their pets.
- “She had a long day at work. She just wanted to get home to her dog. Which was crazy, because I’m like—I have a dog!” – Trey [08:26]
- Trey later asks Julie for her number and arranges a date.
3. The Date: Good Vibes, Short Time
(09:12–09:53)
- Trey and Julie meet for drinks, share plenty of jokes about the fateful bus, but the date lasts less than an hour. Trey enjoyed her company but noticed she was shy.
4. Why Is Julie Not Responding?
(10:48–13:06)
- Despite a nice date, Julie does not reply to Trey's texts or voicemail.
- “I sent a few texts, weren’t responded. ...I also called her but left a voicemail and I haven’t heard back.” – Trey [12:16]
- Trey remains respectful, avoids double-texting, and keeps his message sweet.
5. Calling Julie: The Truth Comes Out
(13:01–16:43)
- The show calls Julie live; she acknowledges the date and compliments Trey as “fantastic”, “consistent”, and “what you see is what you get.”
- “He’s a very—what you see is what you get. Good person.” – Julie [14:22]
- Julie reveals she’s in a “situationship”—not a full relationship, but more than just casual—with another man. She admits she cut the date short due to guilt.
- “…it’s complicated. Like, he’s very uncomplicated and I’m in a little bit of a complicated situation.” – Julie [14:29]
6. The Bombshell: The Situationship Explored
(16:43–18:29)
- Julie clarifies that her “situationship” is with a man in prison.
- “My situationship is actually long distance because he is locked up.” – Julie [17:20]
- She met him a week before his incarceration, and now visits him every three months.
- “We had met, like, the week before he got locked up, and we kind of hit it off.” – Julie [17:50]
- “…I can’t emotionally untangle myself from it.” – Julie [18:18]
- Trey is surprised but remains empathetic and optimistic.
- “I understand. Sometimes things get complicated, then they get uncomplicated. Life is messy. I get it.” – Trey [16:36]
7. Trey’s Offer, Julie’s Hesitation, and Decision Time
(18:43–20:12)
- Trey gently suggests another date, believing he could show her he’s a better fit.
- “If there’s any chance that you might be interested, I’d love to go out again and show you, really, that maybe I’m better than the other situation.” – Trey [16:43]
- The hosts urge Julie to reconsider the prison situationship.
- “How long is this other guy locked up for?” – Brooke [19:08]
- “Do not waste all your pretty on that. It’s a long situation!” – Brooke [19:14]
- Julie agrees to see Trey again, despite her ongoing connection with “jail guy.”
- “If he’s okay knowing all of this and that this is still happening in the background, why figure this out?” – Julie [19:51]
- “Yeah, I mean, you won’t even be thinking about jail guy.” – Trey [20:00]
- Trey scores a second date—albeit a complicated one.
8. Hosts’ Reactions and Reflections
(22:17–23:37)
- Brooke and Jeffrey reflect on the surreal dating situation and commend Trey’s positive spirit.
- “Bless Trey’s heart for being willing to give it a shot and try to win her over for the next three years.” – Jeffrey [23:08]
- They joke about potential prison listener updates and hope for another update from Trey.
Notable Quotes & Memorable Moments
-
On Trey’s Resilience:
- “Trey has already suffered through the trifecta of humiliation. He’s been through it all. But he. He’s back. That’s what’s important.” – Jeffrey [06:13]
-
When Julie Reveals the Truth:
- “My situationship is actually long distance because he is locked up.” – Julie [17:20]
-
Hosts’ Genuine Encouragement (and Sarcastic Banter):
- “What a guy.” – Brooke [16:42]
- “Would you be willing to fight this guy after three years when he’s released and prove that you’re the one for Julie?” – Jeffrey [19:19]
- “If I can see a mugshot before, so I can better assess it.” – Trey [19:26]
Important Timestamps
- 04:38 – Recap of Trey's romantic struggles and past humiliation
- 06:44 – Trey describes meeting Julie during his act of kindness
- 09:12 – Trey recounts their brief, pleasant first date
- 12:16 – Trey discusses his (unanswered) polite follow-up attempts
- 13:01 – First contact with Julie; her initial reaction
- 14:29 – Julie admits to a current “complicated” status
- 17:20 – Julie drops the prison “situationship” bombshell
- 18:43 – Trey expresses his willingness to keep pursuing Julie
- 19:14 – Brooke urges Julie to let go of her incarcerated boyfriend
- 19:51 – Julie tentatively agrees to another date
- 22:17 – The hosts react, reflect, and speculate about Trey’s future
Episode Summary
This episode of "Second Date Update" highlights the unpredictable, often messy reality of contemporary dating. Trey, a much-beloved (and often pitied) recurring guest, chases hope after a history of humiliations—this time after heroically stopping to help a broken-down bus. His burgeoning connection with Julie hits a wild snag when she confesses to having an ongoing “situationship” with a man in prison. Despite the odds (and the ongoing every-three-months visits to “jail guy”), Trey’s open-hearted optimism wins Julie’s agreement to one more date.
For listeners new to Trey's saga or just tuning in for the laughs and dramatic surprises, this episode delivers a full spectrum of human awkwardness, hope, and humor—with hosts who aren’t afraid to poke fun at love’s perplexing twists.
To reach out for a "Second Date Update" or follow more stories, catch the full show over at Brooke and Jeffrey.