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November 3, 2025 18 mins

We needed the listener on the phone today to be 100% HONEST about what happened with his date, and that proved to be harder than we realized…

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Episode Transcript

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Speaker 1 (00:00):
You did it.

Speaker 2 (00:00):
You made it through the Halloween weekend. We're so glad
you were here. It's Brook and Jeffrey and this is
your Second Date Update podcast. So thanks to listen to
our full show yesterday, our Halloween show, which is always
so fun. Yeah, you know, before we get to our
brand new Second Date today, we do love to highlight
some of your coment.

Speaker 3 (00:18):
Yes, Amelia said, this might sound creepy, but every day
I sit in front of my laptop waiting until you
guys upload a new episode. I'm a seventeen year old
entrepreneur in Ireland and I genuinely can't focus until I
hear you guys screaming in my.

Speaker 4 (00:31):
Ear organized chaos.

Speaker 1 (00:35):
Yeah, I love it. We'll keep her out there, Amelia.
That's rad. Thank you, and your brand new Second Date
starts right now.

Speaker 4 (00:42):
Sorry, I'd like to invest five dollars in your startup company.

Speaker 1 (00:44):
Oh yeah, I just want to put that up us right.

Speaker 4 (00:47):
Oh yeah, conversion, Never mind, I'm backing out of our deal.
Second Date Update. Welcome back to Brook and Jeffrey in
the morning, another Second Date Update, and just like many
of our male listeners who come on to this segment,
today's listener James says he has no idea if he

(01:08):
did anything wrong on.

Speaker 1 (01:10):
His first I'm sure it was not his fault.

Speaker 4 (01:13):
No, probably not. She's like, well, he set my house
on fire. And he's like, oh, wait a minute, I forgot.

Speaker 1 (01:20):
I forgot to tell him that that's a thing.

Speaker 4 (01:23):
But there is a gray area in there. That's why
we're gonna implement this sound. Oh that's an RFA, a
red flag alert.

Speaker 1 (01:32):
Oh I like it.

Speaker 4 (01:33):
Anytime you hear that noise, we need to stop what
we're doing and discuss. Could she have maybe taken that
okay the wrong way?

Speaker 1 (01:41):
Okay, who's in charge of the sound? You are, Jeff,
that's a red flag.

Speaker 4 (01:45):
Don't question who's in charge in this room ever.

Speaker 1 (01:47):
Bro say the power is not in the right hand.

Speaker 4 (01:51):
Turn off Brooks mike for the next ten seconds. Thank you,
let's welcome. Let's welcome James to the show. James, how
you doing, man? You don't have to be afraid.

Speaker 2 (02:01):
Of I tried to hear what his voice sounded like
before he decided if it was a red flag, you
need to hit the button.

Speaker 1 (02:06):
I'm scared the button's going to go off.

Speaker 4 (02:07):
Don't say anything weird. His fingers literally on the buttons,
no pressure, Just tell us how your date went with
who are we calling today?

Speaker 5 (02:16):
I went on a date with Chelsea.

Speaker 4 (02:18):
Chelsea Okay, he remembered the name right away. I almost
hit the hit the sound effects. But we're good on that.
We have a green flag button. There we go. This
is gonna get annoying, all right, So tell us how
how did you meet Chelsea?

Speaker 5 (02:33):
Okay, so we met on a dating app.

Speaker 4 (02:38):
That's where people meet now, Jess, I agree, But which
dating app we met on?

Speaker 5 (02:44):
Bumble?

Speaker 1 (02:45):
That's a green flag.

Speaker 4 (02:46):
That's all right, off the buttons. It's it's a medium.
It's I'm always little questionable geting girls all the power.
But let's keep going. What did you and Chelsea bond
over when you first met?

Speaker 5 (02:57):
Yeah, things are like pretty natural right from the star.
And one of the things we boughted over was hot sauce,
Like we both love really spicy food.

Speaker 4 (03:07):
And I was like the recorder song we also have
hot cross runs.

Speaker 2 (03:11):
Yeah, hot sau and such an easy transition to we
need to go get spicy food together.

Speaker 4 (03:17):
Is that what you did? Did you lead it into
like we should try some hot sauce somewhere?

Speaker 6 (03:21):
Yeah?

Speaker 5 (03:22):
Actually, and we went to this taco place sweet. It
was great. It was great. Uh, there was live music,
so it was like pus cool setting right off the bat.
But it was really loud in there, and my hearing
isn't the best because I've played drums in my past,
like way too loud, and so my earring's kind of going.

(03:42):
So I did ask the waiter if we could like
move tables so I could hear her better.

Speaker 4 (03:47):
Yeah, you could come across as high maintenance former server.
I think I remember people asking yes, and sometimes it's
actually nice because he's been considered a hurt. Now that
Jose approves it, I agree, that's flag.

Speaker 2 (04:05):
Okay, keep going, I want to hear something worse happen
on the sha.

Speaker 4 (04:09):
Eventually you found a table that was quieter.

Speaker 5 (04:12):
Yeah, it was quieter, and we showed each other pictures
of our dogs. Were both dog parents really nice.

Speaker 2 (04:18):
Okay, So I mean, you guys are vibing on all
these different levels.

Speaker 1 (04:22):
I mean, was there anything awkward?

Speaker 5 (04:24):
Yeah? Exactly, Like I felt like we really connected and
there wasn't anything awkward at all, at least not from
what I could tell. That. She was super cute and
we felt really comfortable talking to each other. I wasn't
even like pretending and trying to be cool. I was
just being myself.

Speaker 4 (04:40):
Yeah, Jeff's right, hits the button. I'm sorry.

Speaker 1 (04:45):
That is exactly what people want on a date.

Speaker 4 (04:47):
No, I know how it is. Once you get deeper
into the relationship a year, two years in and the
real you comes out, that's when everything turns over.

Speaker 2 (04:56):
Oh, that's when you know you're with the right person.
Is when you feel like you can be fully yourself.

Speaker 4 (05:02):
And that's when your husband spits sunflower seeds all over
the house.

Speaker 1 (05:05):
It's a habit that's annoying it.

Speaker 4 (05:08):
It's the real hymn. Tell us this, was there any
romance happening between you, any flirtations, any kissing?

Speaker 5 (05:16):
There we go So unfortunately there wasn't a kiss, but
not because I didn't try.

Speaker 1 (05:21):
Oh did you get turned down?

Speaker 4 (05:23):
Did she reject you?

Speaker 5 (05:25):
Not really? Like she drove me to my car because
I kind of parked far away and I'm like a
good bit taller than her. Though, as I was getting
out of a car, like she moved her head toward
mine and then like I leaned down and kissed like
the top.

Speaker 2 (05:40):
Of her head.

Speaker 3 (05:41):
Oh was it awkward or cute because a forehead kiss
could be cute.

Speaker 5 (05:45):
It wasn't really her forehead. It was like the top
of her head.

Speaker 1 (05:47):
It's like hair. Oh my gosh, yeah, got so much
hair in my mouth.

Speaker 4 (05:51):
Yeah, it's like you're kissing your kid before you send
them off to school.

Speaker 1 (05:55):
That is an awkward ending. Totally, yeah awkward.

Speaker 4 (06:00):
Okay, sure, And I totally could have buzzed you for
not doing valet parking yourself, but I didn't do that.
I'm giving you credit there, give yourself.

Speaker 1 (06:07):
Agreement what taco spot has.

Speaker 4 (06:10):
Yeah, a good job, Jeff for being understanding of other
people's plate. I feel really good about anyway, after the
head kiss, how did you leave it? Like?

Speaker 5 (06:23):
I just walked back to my car. She drove off
and I haven't heard from her.

Speaker 6 (06:27):
Then.

Speaker 1 (06:27):
Were you just walking back to your car being like God,
why did I kiss.

Speaker 5 (06:30):
The top of.

Speaker 4 (06:33):
You?

Speaker 5 (06:33):
Know?

Speaker 4 (06:33):
You blew it, especially when you could have used tongue
and you didn't. At least it shows that you're into it.
I'm just gonna fix.

Speaker 6 (06:43):
It.

Speaker 4 (06:43):
Shows that you wanted it.

Speaker 1 (06:44):
But you missed red flag yourself.

Speaker 4 (06:48):
Green flag for effort. And how long has it been
since the awkward top of the head kiss.

Speaker 5 (06:54):
It's been a solid two weeks flag finally when we
agree on yeah, any communication at all? Uh No, she
hasn't maken me back. That's why I am calling you guys.
Hopefully you can help me. Like, did I somehow turn
her off or offend her or something?

Speaker 2 (07:10):
I don't know.

Speaker 4 (07:11):
Well, the head's awkward, but that's not a deal breaker
for sure.

Speaker 1 (07:14):
Will we not use the sounders when we call her?

Speaker 4 (07:17):
Well, at that point she's just going to be telling
us what her red flags were, so it's not going
to feel good to buzz it. But if she answers
the phone on the first try, red flag, she should
be Yeah, it's a little bit too over eager, could
be a scammer calling her, and I don't trust that.
So hopefully she doesn't pick up for a few times.
But when she does, listen for second date update Red

(07:40):
Flag edition, we'll do it right after this. Hold on
second date update? Are you just joining us for the
second date update? We played a little game of spot
the possible red flags?

Speaker 1 (07:54):
Why would we not call it red flag? Green flag?
And we it was you Yeah, whenever you want.

Speaker 4 (07:59):
It was a fun time, wasn't it? And several potential
flags did come up one after they were seated, and
James asked the waiter if they could move tables farther
away from the live singer so.

Speaker 1 (08:12):
That he could actually hear her. I wanted to listen.

Speaker 4 (08:15):
Could have come across as he's a high maintenance guy. Also,
maybe she thinks he hates music. Nobody wants to someone
that's anti music. And the second possible red flag happened
when he went to kiss her but she moved so
his lips touched the top of her head aka the
Proud Father kiss. Not a move you want to be pulling,

(08:37):
at least not on a first date. And then two
full weeks with zero communication from Chelsea not a good sign. Jeff, Yeah,
I mean.

Speaker 1 (08:46):
The last two. I agree with Jeff, because even if.

Speaker 4 (08:49):
You don't like a guy at all, you'll at least
drunk text him at two am one night, right, alexis.

Speaker 1 (08:54):
Yeah, probably high like a photo exactly.

Speaker 4 (08:58):
Slip up will happen. So we are officially though, we're
going to retire the red flag alert. That's the last one.
It had a good run for at least half a segment.
But from now on, let's just try to use our
voices to talk and communicate like humans.

Speaker 1 (09:13):
Do are ok Yeah, why are you saying.

Speaker 4 (09:16):
That it's a group thing. Let's all agree together, all right.
I'm on an island. I will try to communicate all
on my own. And I haven't heard at all from James. James,
are you still on the phone.

Speaker 2 (09:28):
Yeah, I'm here, okay, Okay, he's listening to your monologue
is what he was doing.

Speaker 4 (09:34):
Okay, green flag for being a good listener.

Speaker 1 (09:37):
That's why you wanted the quieter booth.

Speaker 4 (09:38):
All right, let's just call Chelsea. We'll see if she answers.
Here we go, Hello, Hi, are we talking to Chelsea?

Speaker 7 (09:53):
Yeah?

Speaker 4 (09:55):
Hey, Chelsea. This is a radio show called Brooke and
Jeffrey in the Morning, Chelsea. Fun time.

Speaker 1 (10:02):
Oh it feels forced.

Speaker 6 (10:04):
Okay, Hi, why are you calling me?

Speaker 4 (10:08):
This is part of a segment we do call the
second Date Update, where we're trying to get some answers
for one of our listeners about why he hasn't heard
from you since you met up for a date and.

Speaker 1 (10:18):
It was like two weeks ago.

Speaker 5 (10:19):
Me.

Speaker 4 (10:20):
Yeah, yeah, a guy you went out with named James.

Speaker 2 (10:24):
Oh, okay, remember spicy James.

Speaker 1 (10:28):
It loves tacos.

Speaker 4 (10:29):
Yeah, especially he emailed us because he told us about
your date, and honestly, he has no idea why you
wouldn't be calling him back in the last couple of weeks.

Speaker 6 (10:42):
Wait, why why would I even tell you guys? Why
would I go into this on the radio?

Speaker 1 (10:46):
This is so weird because he's like disappointed.

Speaker 2 (10:49):
I thought it was like such a cool compliment. He
told us that he felt like he could fully totally
be his authentic self around you.

Speaker 4 (10:58):
Yeah, okay, make sure did you feel like that was
the case.

Speaker 6 (11:03):
Yeah, maybe he was his authentic self. If that authentic
self is like pretty rude?

Speaker 1 (11:09):
Whoa rude? That's so interesting. He didn't come across his
rude at all.

Speaker 4 (11:16):
I felt like he was too timid. Yeah, since we
did hear a few things that happened on the date,
can we ask was it when he asked to move
tables to be far away from the singer that was
annoying him? Well, I don't know. I'm leaving it open
for to fill in.

Speaker 1 (11:32):
The blank, not leading the witness at all.

Speaker 4 (11:34):
No, No, Chelsea, was it that that was fine?

Speaker 6 (11:38):
That didn't bother me?

Speaker 1 (11:39):
Yeah, because that was sweet.

Speaker 2 (11:40):
He said he wanted to be able to hear you better,
so you guys could have some good conversation.

Speaker 6 (11:44):
Yeah, but it wasn't good conversation because he made me
kind of mad.

Speaker 1 (11:49):
Oh my god, I know he has no idea.

Speaker 4 (11:52):
Yeah, we didn't hear any like any moment like that
come up on your date.

Speaker 6 (11:55):
So him and I had been getting to know each
other for kind of a while.

Speaker 8 (12:00):
And the app and like we did bond over our
dogs and we've been telling each other stories about our pets. Cute,
And on the date with James, I started to tell
him a story that I guess I had already told
him and forgot, and he literally interrupted me and was like,
sorry to interrupt you, but you've already told me this,

(12:21):
And he wanted me to stop telling my story, Like
that's so.

Speaker 1 (12:25):
Rude, that's interesting. Why do you think it's rude?

Speaker 5 (12:30):
Though?

Speaker 7 (12:30):
What do you mean why do I think it's rude? Yes,
he interrupted me in the middle of my story and
basically told me to stop telling the story.

Speaker 4 (12:37):
Oh, okay, okay, I mean Brook, would you like it
if you were trying to tell someone a story and
they were like, no, no, no, no, don't I already know.

Speaker 1 (12:44):
That's wy I appreciate it when people tell me I'm
repeating myself. I tell the same stories all the time.

Speaker 4 (12:48):
I get it, but it's kind of weird when it's like,
this is your first face to face meeting and they're like, yeah,
I've already heard it.

Speaker 2 (12:54):
Okay, So I could see you being a little annoyed
by that, but I can't imagine it being such a
big deal.

Speaker 1 (13:00):
It's the whole reason you never want to see him again.

Speaker 7 (13:03):
Yeah, a big dealer or not. It made me mad.
I thought it was rude.

Speaker 6 (13:07):
It gave me the ache.

Speaker 4 (13:08):
I hate interrupt, but you did already tell us that
you made us mad. I'm just we're kind of short
on time, is the only reason why, Because I have
to let you know that James has been listening to
this too on the other line and wants to talk
to you.

Speaker 1 (13:22):
That's a new story she hasn't heard.

Speaker 4 (13:23):
Yeah, new information, right.

Speaker 6 (13:26):
Wait he just heard all of that.

Speaker 4 (13:28):
Yeah, yeah, theoretically if he was listening. James.

Speaker 8 (13:32):
Hey, Chelsea, I, oh my god, we're going to lead
with their James.

Speaker 5 (13:40):
Sorry, I had to go this radio route, but I
just couldn't hear back from you. I didn't know what
was going on and upset.

Speaker 4 (13:49):
Yeah, James, did you hear the part where she didn't
like that you interrupted her story and said, no, I've
already heard that before.

Speaker 5 (13:55):
Yeah, but okay, it was a long story and I
didn't want it to take like another ten minut. We're
trying to have a good conversation, so.

Speaker 3 (14:03):
The story was too long for you' I was gonna say,
if it was a long, boring story you already heard,
I would cut someone off.

Speaker 1 (14:09):
But you have to think of a more creative way
to do it.

Speaker 7 (14:11):
Yeah, you thought my story was too long and boring.

Speaker 5 (14:16):
Not boring is just so sad, like when you told
me on the app about your dog you grew up
with and what happened, Like it was really sad and
I didn't.

Speaker 7 (14:25):
Want okay, but you should let all that finish the story.
Like maybe I like to retell my stories sometimes because
sometimes you're not listening to the full thing anyway every
single time, so you're gonna get different Easter eggs every
single time I tell it.

Speaker 4 (14:41):
I may remember another fact that I forgot lost time.

Speaker 2 (14:44):
Not only that, but if it's a sad story, you
don't interrupt somebody who's being emotionally vulnerable.

Speaker 1 (14:49):
Lad like that that.

Speaker 2 (14:51):
I can see James where maybe that was a bad timing.

Speaker 5 (14:55):
But we were trying to have a good fun night, Like,
why bring it down?

Speaker 4 (14:59):
I didn't want Yeah, and you ruined that.

Speaker 6 (15:03):
Yeah.

Speaker 4 (15:04):
It sounds like she was looking for like a safe
space to tell her truth and you were like no
room for that.

Speaker 2 (15:10):
And a green flag right now, James would be you
just owning that mistake and apologizing, not trying to make
excuses for it, right or downplay her feelings.

Speaker 4 (15:19):
Yeah, And Chelsea, can I ask you, is that the
reason why at the end of the night you turned
your head when he went in for a kiss and
just got the top of your of your skull.

Speaker 5 (15:30):
Yeah.

Speaker 7 (15:31):
Actually, after he interrupted me from telling my story, I
just got the complete egg and that.

Speaker 5 (15:37):
Was it for me.

Speaker 2 (15:43):
Okay, can you are you a person that has ever
come back from an ick?

Speaker 1 (15:48):
No?

Speaker 4 (15:49):
If you agreed to listen to your story in its
entirety the next time you met up just to make
up for I mean.

Speaker 7 (15:56):
Then I would just be thinking the whole time.

Speaker 6 (15:58):
Have I told the story? Or is he bored? Or like, yeah,
it's just not going to work.

Speaker 1 (16:03):
She keeps making points that I can see what she's say.

Speaker 5 (16:06):
Yeah, you know, I know I feel the same way.
There's like nothing I can say here.

Speaker 1 (16:11):
Wow, say sorry, yeah, you never do it again.

Speaker 4 (16:14):
I know what I want to say. I want to
ask if you two will go out on another date again,
and we'd be willing to pay for it. But that's
really comes down to you, Chelsea, if you're willing to
give him one more chance.

Speaker 6 (16:26):
Yeah, No, it's no for me. I think you should
just take it as a learning lesson for his next date.

Speaker 5 (16:32):
Okay, maybe maybe you should learn like how to read
a room and not like bring the whole room down.

Speaker 4 (16:40):
You're not backing down.

Speaker 5 (16:43):
No, she's being rude to me. She's not even giving
me another chance.

Speaker 1 (16:46):
Stories about like her childhood dog die, That's what it
sounds like.

Speaker 7 (16:50):
No, I rescued him from a tree and then he
fell and died.

Speaker 4 (16:54):
Oh Brook, why would you even bring that up?

Speaker 5 (16:58):
Brook?

Speaker 2 (16:59):
Yeah?

Speaker 4 (17:00):
Red flag for the segments that one. Yes, don't ask
these questions ever again, Jeffrey in the morning. All right, listen,
I'm sorry I had to bring back the red flag
alert out of retirement at the end there, But Brooke
crossed the line. We all agree we need yea.

Speaker 1 (17:14):
Yeah, No one else wanted to closure on what happened
with No.

Speaker 4 (17:17):
No, I don't think we needed any more details.

Speaker 1 (17:19):
Id of trust that there was a reason to cut
the story off.

Speaker 5 (17:21):
Yeah.

Speaker 4 (17:22):
Yeah, it was a little bit hard because I felt like,
actually both of them had decent points in the conversation.

Speaker 2 (17:28):
I mean, if it was a debate like in high school,
I think she won by one point.

Speaker 1 (17:31):
Oh yeah, you know it was a debate.

Speaker 4 (17:34):
Yeah, she came out on top. But I also think
that they probably should have gone out again because it
felt like something you could definitely work through if you
talked about it. Yeah, totally.

Speaker 1 (17:43):
I think this girl has zero patients.

Speaker 4 (17:45):
She should have brought it up during the date and said, sorry,
I think it's rude for you to interrupt me telling
my story again, and they could have quashed it right
there and moved on.

Speaker 1 (17:53):
Nobody likes doing that, jeff that's the confrontation.

Speaker 4 (17:56):
That's true. But if you want to hear all of
our stories, the second day ones are awkward tuesdays. All
of our content is up online. You can check it
out wherever you get your podcasts at Brook and Jeffrey
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Hosts And Creators

Brooke Fox

Brooke Fox

Jeffrey "Young Jeffrey" Dubow

Jeffrey "Young Jeffrey" Dubow

Jose Bolanos

Jose Bolanos

Alexis Fuller

Alexis Fuller

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