October 8, 2025 • 7 mins
First dates can be tricky, but some questions are absolute deal-breakers. On this episode of The Jubal Show, we dive into the top questions you should never ask on a first date—from awkward money talks to weird personal probes that can ruin the vibe instantly. Hear hilarious real-life stories, expert tips, and learn how to navigate dating without sabotaging your chances. Perfect for singles, daters, and anyone who’s ever experienced a cringe-worthy first date!
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:01):
Good morning.
Speaker 2 (00:02):
Well, I don't know about you, but I think this
first date is going great.
Speaker 3 (00:08):
Wow.
Speaker 2 (00:08):
I mean, is this even a wing doome? Because to
me it feels like heaven?
Speaker 1 (00:13):
Side note? Is it coolfy split the bill because I'm
a little trapped for cash right now?
Speaker 2 (00:17):
Ady?
Speaker 3 (00:17):
Who?
Speaker 1 (00:18):
Since it's our first date?
Speaker 2 (00:19):
I just wanted to know a little bit about your family, specifically,
are your parents still married? And would they approve of
us hooking up in this wingdow and bathroom?
Speaker 1 (00:26):
Ah?
Speaker 2 (00:28):
No, wrong answer to that, because if they would, we
can just keep it out or a little secret. You
and these living pepper wings be the only ones that know.
Wait a minute, what's going on?
Speaker 1 (00:38):
You have?
Speaker 2 (00:38):
You're leaving, you haven't even paid your portion of the
bill yet. It's a double show. And let's face it,
first dates can be awkward and sometimes it's hard to
know what to talk about because you want to get
to know somebody, but you don't want to ask something
that will completely ruin the date. Well Around Relationship Expert
just published a list of the questions you should never
ask on a first date, and we'll go over it
(00:59):
right after this so you can know exactly what not
to say on your next date.
Speaker 1 (01:03):
It's a jebile show.
Speaker 2 (01:04):
I had a guy ask me once on a date
if i'd be with a man who had a third nipple.
Then he smiled at me and lifted up his shirt
and pointed at it. A We did not end the
date with a kiss, and yes, I ghusted him. That's
a text message that we just got in at four
to one oh six one. Text us with the worst
thing You've ever been asked on a first date? Because
a relationship expert has just released a list of the
(01:26):
top things you should never ask on a first date.
And I've heard stories of people saying ridiculous things on
first dates. But what are the top things that you
should never say on a first date? Here's the first
question they say you should never ask. How do you
think this date is going so far? That's a weird question.
Speaker 3 (01:44):
I feel like if you have to ask it, it's
not going very well. Oh if you know what I mean,
Like it's kind of awkward, you.
Speaker 1 (01:50):
Don't know what you're doing.
Speaker 2 (01:51):
Yes, I should be like a lull in the conversation,
one of those awkward ones and when everybody just kind
of goes like after I laugh, just like, so, how
do you how do you think this date is going
so far?
Speaker 1 (02:01):
The answer to that is usually going to be bad.
I mean, it gives you an out. Ask that question.
If it's going that way, give yourself an out. I
gotta go. I'm thinking it's going very well. I've been
asked that, I but I've never used it as an out.
You've actually been asked that, Victoria.
Speaker 4 (02:13):
Yeah, but I feel bad saying oh, it's going terrible, Like,
what do.
Speaker 1 (02:16):
You think it's about? Put somebody in a weird spot.
Speaker 3 (02:19):
I think we just need to be empowered to be honest,
because otherwise we're wasting our time, their time.
Speaker 1 (02:23):
And you know, you could just go home, go.
Speaker 2 (02:24):
To sleep, exactly, it would be nice, especially if both
of you guys felt that way.
Speaker 1 (02:28):
Exactly. How do you think this date is going right now? Terrible?
Speaker 2 (02:31):
Yeah?
Speaker 1 (02:31):
Me too? You want to just go? Yeah? It sounds
so nice, isn't it. I would respect you so much more.
Speaker 2 (02:37):
Really, Yes, we're going over a list of the top
questions you should never ask on a first date. But
that doesn't happen to me anyway, keep mine. Are you
seeing anyone else right now? You can't not on a
first date. No, you just assume they are why are
you asking?
Speaker 4 (02:53):
Also, you're only on one date with them, like nothing's exclusive?
Speaker 1 (02:56):
How insecure are you? That is not a card to
play right right.
Speaker 2 (03:00):
I've never had anybody ask me that on a first date,
but I imagine it probably does get asked a lot.
I've seen mostly dudes asking that question.
Speaker 1 (03:07):
For some reason.
Speaker 3 (03:07):
You ask that question, and it's usually not on a
first date, but it comes up with usually in like
then first like two to three, and you just look at.
Speaker 1 (03:13):
Him and I'm like, what do you want me to say?
I'm like, I just go, what do you think? Are you?
Are you seeing anybody else? Because you are? I know.
Speaker 2 (03:21):
I've had friends that like we're upset about it, like
she's totally dating other people, and I'm like, so are you? Yeah,
but like it's different. I'm like, no, it's not. It's
not different at all. It's just that you're jealous. Another
question that says you should never ask on a first date.
Speaker 1 (03:40):
Do you want to split the bill?
Speaker 3 (03:42):
Oh?
Speaker 1 (03:43):
I think that's that bad, really bad. Yeah, I don't
mind that.
Speaker 4 (03:45):
I also feel bad because I feel bad like making
the guy pay for everything that, like if he does
like say no to that and.
Speaker 1 (03:52):
He gets the bill then I'll go get like ice
cream or something.
Speaker 2 (03:55):
If if he does the sweet after, it means I
have more money, so I can go grab an ice
cream cone and go home.
Speaker 1 (04:04):
That actually feels like it's more you. That really does.
Speaker 4 (04:07):
Yeah, if you buy it for both them, but we're
getting our separate ones, like.
Speaker 1 (04:12):
Split up it right, right right.
Speaker 2 (04:13):
There's another question that says that you should never ask
on a first date.
Speaker 1 (04:17):
Do you believe in marriage? They say it's a bad
question to ask on a first date. Why first? Why
do you ask that on the first date? Because why if.
Speaker 3 (04:23):
You don't believe in marriage and you do, and then
you're already starting off this entire little whatever rendezvous depending
on what you want out of a relationship. But if
marriage is your endgame and that person doesn't want it,
don't you want to know sooner than later?
Speaker 1 (04:35):
Not on a first date. I don't mind way too early.
It's probably good to know, I guess to get out
of the way.
Speaker 2 (04:42):
So you're like, Okay, well, if I want marriage and
she doesn't, then I can still date her and we
can just kind of mess around. But I know it's
not gonna anything serious.
Speaker 3 (04:49):
Yeah, exactly, So you kind of at least know where
you're going with it. That one's not weird to me.
Speaker 4 (04:53):
But then also I feel like that's like one of
those questions where like people could run from because like, oh,
she's trying to get married asap, Like I'm gonna try
to do that.
Speaker 1 (04:59):
This is an age thing.
Speaker 3 (05:00):
Oh you're twenty five, and therefore anybody would run away
from you right now.
Speaker 1 (05:04):
That will be the one that says, do you believe
in marriage? Let's do it.
Speaker 2 (05:07):
There's a courthouse right now. You got you kids, This
is great, We've got a family going.
Speaker 1 (05:14):
We're good.
Speaker 2 (05:15):
We're going over a list of the top things you
should never ask on a first date. According to a
relationship expert, why are you still single?
Speaker 1 (05:24):
Oh?
Speaker 4 (05:25):
A bad question to ask. I feel like guys think
that's a compliment when they.
Speaker 2 (05:29):
Ask, I think they're trying to compliment, but it doesn't
sound good at all. No, Oh my gosh, you're still perfect?
How are you still single? Aka? You must be nuts?
Speaker 1 (05:38):
But it's so loaded.
Speaker 3 (05:39):
I'm finding that that question actually is even more loaded
than innocent, because I get it regularly in my DMS,
and I don't know.
Speaker 1 (05:45):
These people what.
Speaker 3 (05:46):
But the thing is is, like so many people have
lived lives that you know. Maybe you've had your heart broken,
maybe you need to be alone. Maybe you just feel
like you're just getting your bearings back, like there are
so many other things and what I don't want to
do when you ask me why I'm still single, this.
Speaker 1 (05:59):
Is our crying. It could be like, you know what,
I'm really proud of myself, right, it's fine while I'm
not divorced. Oh yeah.
Speaker 2 (06:11):
I think guys are trying to say, like, I think
you're amazing and I would date you in a heartbeat.
I can't believe those other guys were idiots and let
you go. I think that's what they're trying to say,
but it comes off like, wow, you have to be
insane because that's the only reason you're single.
Speaker 3 (06:26):
Like I'm crazy say that other part against people can
write it down.
Speaker 2 (06:30):
I think you're amazing, and I'm baffled how anybody is not.
I think they're idiots. For I don't remember what I
said now, I'm I can't go back to that moment. Yeah,
I like it, I like something like that, but yeah,
I like basically I like you a lot, and I
think that if anybody let you go, they're dumb.
Speaker 1 (06:45):
That's it. You could just say that, yeah, that is
the quickest way to get me.
Speaker 2 (06:51):
And the number one question they say you should not
ask on a first date how much money do you make?
Speaker 1 (06:57):
Oh? You kind of ballpark? You don't have to ask
that question. Just ask you about their job? Does it matter?
Look at their shoes? So what cars yours?
Speaker 2 (07:06):
In the parking lot? The Ford Festiva? Hey, I gotta go.
Good morning.
Speaker 2 (00:02):
Well, I don't know about you, but I think this
first date is going great.
Speaker 3 (00:08):
Wow.
Speaker 2 (00:08):
I mean, is this even a wing doome? Because to
me it feels like heaven?
Speaker 1 (00:13):
Side note? Is it coolfy split the bill because I'm
a little trapped for cash right now?
Speaker 2 (00:17):
Ady?
Speaker 3 (00:17):
Who?
Speaker 1 (00:18):
Since it's our first date?
Speaker 2 (00:19):
I just wanted to know a little bit about your family, specifically,
are your parents still married? And would they approve of
us hooking up in this wingdow and bathroom?
Speaker 1 (00:26):
Ah?
Speaker 2 (00:28):
No, wrong answer to that, because if they would, we
can just keep it out or a little secret. You
and these living pepper wings be the only ones that know.
Wait a minute, what's going on?
Speaker 1 (00:38):
You have?
Speaker 2 (00:38):
You're leaving, you haven't even paid your portion of the
bill yet. It's a double show. And let's face it,
first dates can be awkward and sometimes it's hard to
know what to talk about because you want to get
to know somebody, but you don't want to ask something
that will completely ruin the date. Well Around Relationship Expert
just published a list of the questions you should never
ask on a first date, and we'll go over it
(00:59):
right after this so you can know exactly what not
to say on your next date.
Speaker 1 (01:03):
It's a jebile show.
Speaker 2 (01:04):
I had a guy ask me once on a date
if i'd be with a man who had a third nipple.
Then he smiled at me and lifted up his shirt
and pointed at it. A We did not end the
date with a kiss, and yes, I ghusted him. That's
a text message that we just got in at four
to one oh six one. Text us with the worst
thing You've ever been asked on a first date? Because
a relationship expert has just released a list of the
(01:26):
top things you should never ask on a first date.
And I've heard stories of people saying ridiculous things on
first dates. But what are the top things that you
should never say on a first date? Here's the first
question they say you should never ask. How do you
think this date is going so far? That's a weird question.
Speaker 3 (01:44):
I feel like if you have to ask it, it's
not going very well. Oh if you know what I mean,
Like it's kind of awkward, you.
Speaker 1 (01:50):
Don't know what you're doing.
Speaker 2 (01:51):
Yes, I should be like a lull in the conversation,
one of those awkward ones and when everybody just kind
of goes like after I laugh, just like, so, how
do you how do you think this date is going
so far?
Speaker 1 (02:01):
The answer to that is usually going to be bad.
I mean, it gives you an out. Ask that question.
If it's going that way, give yourself an out. I
gotta go. I'm thinking it's going very well. I've been
asked that, I but I've never used it as an out.
You've actually been asked that, Victoria.
Speaker 4 (02:13):
Yeah, but I feel bad saying oh, it's going terrible, Like,
what do.
Speaker 1 (02:16):
You think it's about? Put somebody in a weird spot.
Speaker 3 (02:19):
I think we just need to be empowered to be honest,
because otherwise we're wasting our time, their time.
Speaker 1 (02:23):
And you know, you could just go home, go.
Speaker 2 (02:24):
To sleep, exactly, it would be nice, especially if both
of you guys felt that way.
Speaker 1 (02:28):
Exactly. How do you think this date is going right now? Terrible?
Speaker 2 (02:31):
Yeah?
Speaker 1 (02:31):
Me too? You want to just go? Yeah? It sounds
so nice, isn't it. I would respect you so much more.
Speaker 2 (02:37):
Really, Yes, we're going over a list of the top
questions you should never ask on a first date. But
that doesn't happen to me anyway, keep mine. Are you
seeing anyone else right now? You can't not on a
first date. No, you just assume they are why are
you asking?
Speaker 4 (02:53):
Also, you're only on one date with them, like nothing's exclusive?
Speaker 1 (02:56):
How insecure are you? That is not a card to
play right right.
Speaker 2 (03:00):
I've never had anybody ask me that on a first date,
but I imagine it probably does get asked a lot.
I've seen mostly dudes asking that question.
Speaker 1 (03:07):
For some reason.
Speaker 3 (03:07):
You ask that question, and it's usually not on a
first date, but it comes up with usually in like
then first like two to three, and you just look at.
Speaker 1 (03:13):
Him and I'm like, what do you want me to say?
I'm like, I just go, what do you think? Are you?
Are you seeing anybody else? Because you are? I know.
Speaker 2 (03:21):
I've had friends that like we're upset about it, like
she's totally dating other people, and I'm like, so are you? Yeah,
but like it's different. I'm like, no, it's not. It's
not different at all. It's just that you're jealous. Another
question that says you should never ask on a first date.
Speaker 1 (03:40):
Do you want to split the bill?
Speaker 3 (03:42):
Oh?
Speaker 1 (03:43):
I think that's that bad, really bad. Yeah, I don't
mind that.
Speaker 4 (03:45):
I also feel bad because I feel bad like making
the guy pay for everything that, like if he does
like say no to that and.
Speaker 1 (03:52):
He gets the bill then I'll go get like ice
cream or something.
Speaker 2 (03:55):
If if he does the sweet after, it means I
have more money, so I can go grab an ice
cream cone and go home.
Speaker 1 (04:04):
That actually feels like it's more you. That really does.
Speaker 4 (04:07):
Yeah, if you buy it for both them, but we're
getting our separate ones, like.
Speaker 1 (04:12):
Split up it right, right right.
Speaker 2 (04:13):
There's another question that says that you should never ask
on a first date.
Speaker 1 (04:17):
Do you believe in marriage? They say it's a bad
question to ask on a first date. Why first? Why
do you ask that on the first date? Because why if.
Speaker 3 (04:23):
You don't believe in marriage and you do, and then
you're already starting off this entire little whatever rendezvous depending
on what you want out of a relationship. But if
marriage is your endgame and that person doesn't want it,
don't you want to know sooner than later?
Speaker 1 (04:35):
Not on a first date. I don't mind way too early.
It's probably good to know, I guess to get out
of the way.
Speaker 2 (04:42):
So you're like, Okay, well, if I want marriage and
she doesn't, then I can still date her and we
can just kind of mess around. But I know it's
not gonna anything serious.
Speaker 3 (04:49):
Yeah, exactly, So you kind of at least know where
you're going with it. That one's not weird to me.
Speaker 4 (04:53):
But then also I feel like that's like one of
those questions where like people could run from because like, oh,
she's trying to get married asap, Like I'm gonna try
to do that.
Speaker 1 (04:59):
This is an age thing.
Speaker 3 (05:00):
Oh you're twenty five, and therefore anybody would run away
from you right now.
Speaker 1 (05:04):
That will be the one that says, do you believe
in marriage? Let's do it.
Speaker 2 (05:07):
There's a courthouse right now. You got you kids, This
is great, We've got a family going.
Speaker 1 (05:14):
We're good.
Speaker 2 (05:15):
We're going over a list of the top things you
should never ask on a first date. According to a
relationship expert, why are you still single?
Speaker 1 (05:24):
Oh?
Speaker 4 (05:25):
A bad question to ask. I feel like guys think
that's a compliment when they.
Speaker 2 (05:29):
Ask, I think they're trying to compliment, but it doesn't
sound good at all. No, Oh my gosh, you're still perfect?
How are you still single? Aka? You must be nuts?
Speaker 1 (05:38):
But it's so loaded.
Speaker 3 (05:39):
I'm finding that that question actually is even more loaded
than innocent, because I get it regularly in my DMS,
and I don't know.
Speaker 1 (05:45):
These people what.
Speaker 3 (05:46):
But the thing is is, like so many people have
lived lives that you know. Maybe you've had your heart broken,
maybe you need to be alone. Maybe you just feel
like you're just getting your bearings back, like there are
so many other things and what I don't want to
do when you ask me why I'm still single, this.
Speaker 1 (05:59):
Is our crying. It could be like, you know what,
I'm really proud of myself, right, it's fine while I'm
not divorced. Oh yeah.
Speaker 2 (06:11):
I think guys are trying to say, like, I think
you're amazing and I would date you in a heartbeat.
I can't believe those other guys were idiots and let
you go. I think that's what they're trying to say,
but it comes off like, wow, you have to be
insane because that's the only reason you're single.
Speaker 3 (06:26):
Like I'm crazy say that other part against people can
write it down.
Speaker 2 (06:30):
I think you're amazing, and I'm baffled how anybody is not.
I think they're idiots. For I don't remember what I
said now, I'm I can't go back to that moment. Yeah,
I like it, I like something like that, but yeah,
I like basically I like you a lot, and I
think that if anybody let you go, they're dumb.
Speaker 1 (06:45):
That's it. You could just say that, yeah, that is
the quickest way to get me.
Speaker 2 (06:51):
And the number one question they say you should not
ask on a first date how much money do you make?
Speaker 1 (06:57):
Oh? You kind of ballpark? You don't have to ask
that question. Just ask you about their job? Does it matter?
Look at their shoes? So what cars yours?
Speaker 2 (07:06):
In the parking lot? The Ford Festiva? Hey, I gotta go.
Host
Jubal Fresh
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