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

Brooke and Jeffrey

iHeartPodcasts

Improv, Society & Culture, Relationships, Entertainment News, Comedy Interviews, Comedy, News

4.8 • 1.7K Ratings

🗓️ 20 December 2025

⏱️ 36 minutes

🔗️ Recording | iTunes | RSS

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Summary

Part 1

After we totally botched a Second Date for a guy a few months ago, he’s back and at this point we’re not sure if he’s trolling us or just likes the punishment. We can't let him down this time!

Part 2

Imagine if you went on a date with a coworker and after the hang out, MULTIPLE PEOPLE are now avoiding you. It happened to one of our listeners and you can hear why in a Second Date!

See omnystudio.com/listener for privacy information.

Transcript

Click on a timestamp to play from that location

0:00.0	It's Brooke and Jeffrey in the morning. This is technical director Ashton coming at you with another classic second day update.
0:07.1	And just for all of you ladies out there, if you like this second date, you like what the guy did on this second date, give me a call.
0:14.1	Most of the time, if you go to a business for some help and they provide horrible service, completely let you down and leave you off worse than when you came in.
0:23.3	Wow.
0:24.0	That would be the end of it.
0:25.3	You would never go back again.
0:27.5	Totally.
0:28.1	You go places for help.
0:29.5	Right.
0:29.9	Not the other way.
0:30.7	That's why we were so surprised after we totally botched a second date for a guy a few months ago.
0:36.3	Oh.
0:36.6	And he's asking us for another one today.
0:39.3	I take back my statement.
0:40.3	Yeah, but we're free.
0:41.3	He's not paying for it, so maybe that's why he's still here.
0:44.3	I mean, at this point, I'm not sure if he's just trolling us
0:47.3	or if he really, really enjoys the punishment.
0:50.3	But his name's Brian, and we're going to hear about his holiday that he had at a Christmas tree farm the other day.
0:57.1	And we promised to give at least 30% effort.
1:02.2	Well, Brooke, 22%.
1:03.9	We don't want to stretch ourselves too far for this.
	...

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