August 29, 2025 • 11 mins
On this episode of “Tommy Talk,” Tommy discusses who should pay for the first date. First dates can be nerve-racking. Sometimes slightly awkward. When that bill comes, what do you do? Tommy shares a story from dating in his early 20’s that has stayed with him to this day.
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:02):
Hey, guys, welcome to Tommy Talk. This is a new
weekly series that is part of my I've Never Said
This Before podcast, where I am talking about things that
I've never really publicly talked about before. It's a wait
for you to get to know me better and hopefully
get a little insight into the advice I am offering
to hopefully make your life a bit easier. And today's topic,
(00:22):
this is a hot topic because I have a lot
of friends who have stories related to this topic, and
that topic is being asked to split the bill on
a first.
Speaker 2 (00:33):
Date, a deal breaker.
Speaker 1 (00:36):
Okay, there is a lot to unpack here, and you
guys are getting some stories from my single dating days,
because sometimes you need to learn from what I've gone
through to help you make decisions for your future.
Speaker 2 (00:52):
I am here to.
Speaker 1 (00:52):
Help you, all right, So let's unpack this for a minute.
I was asked to go on a date by somebody
in my early twenties. For quite a lot long time.
They were pursuing me hard, and for whatever reason, I
was busy. I was working. I was doing a lot
in the modeling world at the time, and I was
on shoots and traveling and whatever. So I just wasn't around,
and finally one night I was around and this person said,
(01:12):
can I please take you out to dinner? And I thought, okay,
why not? Like I have nothing to lose. I think
I was like twenty two maybe. So we go to
this restaurant and it was not inexpensive restaurant, by the way.
So this person picked a very nice place and we
sit down and the server comes over and says, can
(01:32):
I get you guys a cocktail? I think I ordered
a Vaka sota. I think I ordered a double vodka soda.
If I'm being honest. It was in my twenties. And
then this person ordered themself a drink, and the server
began walking away, and then my date said, oh, excuse me,
server comes back, can you please put our orders on
(01:54):
separate tabs?
Speaker 2 (01:59):
I literally was like, wait, what.
Speaker 1 (02:02):
We just sat down seven minutes ago. Why are you
worried about the bill? So then the server walks away.
I'm kind of sitting there awkwardly because now I feel like,
what is this? Like this doesn't feel like a date anymore.
And the person I was on a date, which said, oh,
this just makes the bill easier when it comes like,
(02:25):
kind of laughed it off. So immediately I was a
little turned off by it because I thought, how could
someone be that worried about a bill within five minutes
of being together, yet you asked me to go to
a fairly nice restaurant, Like, what is going on? What
is the vibe here?
Speaker 2 (02:44):
Is this? Is this even a date? Do you just
want a friend? Like? What is this?
Speaker 1 (02:48):
Because I got the vibe you were kind of into me,
but now I'm feeling like maybe you're not.
Speaker 2 (02:54):
So I thought it was super weird.
Speaker 1 (02:56):
It wasn't even at the end of the meal, which
is also in my opinion, and a little odd to say,
will you split the bill with me if you're being
asked on a date? So it just created this super
strange environment. And then what was really weird is for
the rest of the date, it was like it was
like a date, Like this person was trying to be
flirty and was very complimentary and seemed clearly very interested
(03:17):
in me. And then the end of the dinner comes
and the server brings over the two bills, and I
looked over and this person didn't tip very well at all,
which to me is also a deal breaker, like give
a good tip to a server they work so hard.
It is not an easy job, like tip somebody, well
twenty percent minimum for server. Come on, I mean you
(03:40):
just have to. But that's a whole other time we talk,
I guess. So then we pay and this person says,
can I walk you, you know, to wherever you're going next?
Because I made it clear I had plans after, and
I said, oh, you know what.
Speaker 2 (03:53):
I'm good. I'm good. I'm just kind of in a rush.
I'm gonna do a phone call after.
Speaker 1 (03:57):
And they were super insistent, like come on, like, let
me just want I'm not ready for the night to end.
Let me just walk you. Let me just walk you.
And I literally was like what do I say now?
Speaker 2 (04:05):
Now? This is just awkward.
Speaker 1 (04:07):
So I let the person walk me to know the
subway and then they were like, I really hope we.
Speaker 2 (04:11):
Can do this again again.
Speaker 1 (04:13):
I can't even say it right because it was so
it was so weird, and I just remember thinking like,
I will not be calling you. This is totally strange vibes.
And I kind of like hurriedly went down the subway
steps after dodging what I thought was like a kiss
and coming. I'm like, no, no, we're not playing that game.
So get on the subway and go. And this story
(04:36):
got me thinking, is it a deal breaker for you
if somebody wants to split the bill with you on
a first date? And I guess there's a few different caveats, right, Like, listen,
we're in twenty twenty five. I am all for a
quality for all my ladies listening, for all of my
gay men listening, Like if you were like, I don't
need to be bought. I want to be seen as
an equal. I don't need someone to pay for my meal.
(04:59):
Power to you. Yes, yes, yes, I love that. For you,
that's great. But on a first damn date, you shall
let someone take you out. I'm sorry you should. If
you are being asked to go on a date, I
think that that person is responsible for taking you out, period,
point blank. Now that doesn't mean that if you continue
(05:19):
seeing this person on date number two, you say you
got me last time, let me get you this time.
Speaker 2 (05:24):
I love that.
Speaker 1 (05:25):
I am all for a little ping pong in the
relationship like that, or in the dating ship, I should say,
But for a first date, if somebody is setting the restaurant,
which by the way, they're choosing the price point of
the restaurant. They're choosing the location. Maybe you have to
go a little further for this location. They're choosing the time.
It's like a lot on you to accommodate them and
(05:47):
leave everything up to their planning. So the least somebody
can do is pick up a tab if they want
to go out with you, if they want your time,
if they want to take up your Thursday or your
Friday night. It's very simple. Otherwise, don't ask somebody on
a date if you don't intend to take them out right.
Speaker 2 (06:06):
It's just to me.
Speaker 1 (06:07):
Maybe I don't know, maybe it's a little old school
or antiquated, but if I sit down at a table
and we are on a first date and the first
thing you say to me is let's have separate checks,
or if at the end of what I think is
a really great date you say, can we split the bill,
I'm instantly going to think you're not interested instantly, or
that I did something wrong to turn you off from.
Speaker 2 (06:29):
The date, or that you're cheap, which.
Speaker 1 (06:32):
To me is not great because you know, you don't
need to be extravagant, but you also don't want to
come off as like super cheap. That's not fun. So
it just sends the wrong message as well. It's a
very very confusing thing. I think that in this day
and age also a lot of people feel like there's
(06:53):
mixed signals when it comes to dating.
Speaker 2 (06:55):
Right.
Speaker 1 (06:55):
You don't know if someone is super interested in you, you
don't know if they're not. There's a lot of options
are online dating, going on four dates a week. So
if you're really digging someone, as the person who asks
somebody out, show them, like show them by a simple
gesture of covering their tacos and a margarita. That's it,
very very very simple. I think dating is such an
interesting thing, and I think that there's a lot of
(07:16):
people who kind of form these rules in their mind
about dating that really come from nowhere, but then they
stick to them. And I do have a friend who
said on a lot of first dates they always go
in on halves for the bill, and I thought why,
Like I don't understand that. Why And they're like, well,
I don't know if I want to see this person again,
or I don't know if it's going to lead to anything.
So why am I going to waste my money on
(07:37):
somebody if I don't intend or if I don't know
if there'll be anything else with this person, Like I
don't know if they'll say yes to another date with me,
or I don't know if I'm going to want to
go on another date with them if I meet someone else,
And all of that I understand. But it's the game
of dating. It's the price of dating, right. You got
to get in the arena to see what can happen.
If potentially meeting the love of your life means spending
(07:59):
an extra forty bucks on a dinner, then I think
it's worth it. I think it's worth it. And if
you're choosing to go on dates with different people five
nights a week, well that's your decision, bro, Like, that's
up to you.
Speaker 2 (08:10):
You're choosing.
Speaker 1 (08:11):
That doesn't mean that you should make all of these
people you're asking out split the bill. I am so
gung ho on. If you ask somebody out, you need
to pay the bill, period. And I think money's a
really interesting topic in general, especially between friendships and like
should you talk about money?
Speaker 2 (08:27):
Should you not? What do you do when bills come?
Speaker 1 (08:31):
When you're in a group of friends and one friend
got the eighty dollars stake and you got a fifteen
dollars taco Like, that's all different. That's different. That's for
another Tommy talk. There's a lot of Tommy talks that
can come from this, but I am specifically talking about
a one on one date. You ask somebody out, you
take them out. It's very simple to me. I also
think that when you do go on that first date,
(08:54):
there's a lot of a lot of emotion to navigate, right.
You're like, in the we're getting to know you phase,
you're trying to share things about yourself but also seem.
Speaker 2 (09:05):
Not overly open or.
Speaker 1 (09:11):
Crazy or emotional or all the things right, because you're like,
oh my god, I want this person to maybe like me.
So the least that you can do is take the
money out of it, take the money out of the conversation, Like,
just don't make it a thing, pay the bill, have
a great net. If you don't want to see the
person again, fine, it's the price of dating, and move on.
(09:31):
But let me tell you if almost single people out there,
what you don't want to do is sit down at
a restaurant and tell the server to give you separate
checks upon sitting down, because you will not ever, ever
ever date that person again.
Speaker 2 (09:46):
If you are interested in them.
Speaker 1 (09:47):
It is the number one way to run out the door.
I should have run out the door. There were those
little bells on the door, and I should have had
those bells ringing because I was like, why the hell
am I still here. I did not have enough alcohol
at that dinner to get through it, but you know what,
I made it out alive. And you got to go
through some rough dates to meet the right one. And
I am so happy I have met my right one
(10:10):
because there's never been anything like that with this person
in my life.
Speaker 2 (10:15):
Right now.
Speaker 1 (10:15):
My husband has been nothing but wonderful and generous and kind,
and so have I. And like I said, it should
be reciprocal. But a first date, Come on, guys, Come On, guys.
By the Damn Tacos and the Vaka Soda. I've Never
Said This Before is hosted by Me Tommy Dedario. This
podcast is executive produced by Andrew Piglisi at iHeartRadio and
(10:37):
by Me Tommy, with editing by Joshua Colaudney. I've Never
Said This Before is part of the Elvis Duran podcast
network on iHeart Podcasts. For more, rate review and subscribe
to our show. And if you like this episode, tell
your friends. Until next time, I'm Tommy de Dario
Hey, guys, welcome to Tommy Talk. This is a new
weekly series that is part of my I've Never Said
This Before podcast, where I am talking about things that
I've never really publicly talked about before. It's a wait
for you to get to know me better and hopefully
get a little insight into the advice I am offering
to hopefully make your life a bit easier. And today's topic,
(00:22):
this is a hot topic because I have a lot
of friends who have stories related to this topic, and
that topic is being asked to split the bill on
a first.
Speaker 2 (00:33):
Date, a deal breaker.
Speaker 1 (00:36):
Okay, there is a lot to unpack here, and you
guys are getting some stories from my single dating days,
because sometimes you need to learn from what I've gone
through to help you make decisions for your future.
Speaker 2 (00:52):
I am here to.
Speaker 1 (00:52):
Help you, all right, So let's unpack this for a minute.
I was asked to go on a date by somebody
in my early twenties. For quite a lot long time.
They were pursuing me hard, and for whatever reason, I
was busy. I was working. I was doing a lot
in the modeling world at the time, and I was
on shoots and traveling and whatever. So I just wasn't around,
and finally one night I was around and this person said,
(01:12):
can I please take you out to dinner? And I thought, okay,
why not? Like I have nothing to lose. I think
I was like twenty two maybe. So we go to
this restaurant and it was not inexpensive restaurant, by the way.
So this person picked a very nice place and we
sit down and the server comes over and says, can
(01:32):
I get you guys a cocktail? I think I ordered
a Vaka sota. I think I ordered a double vodka soda.
If I'm being honest. It was in my twenties. And
then this person ordered themself a drink, and the server
began walking away, and then my date said, oh, excuse me,
server comes back, can you please put our orders on
(01:54):
separate tabs?
Speaker 2 (01:59):
I literally was like, wait, what.
Speaker 1 (02:02):
We just sat down seven minutes ago. Why are you
worried about the bill? So then the server walks away.
I'm kind of sitting there awkwardly because now I feel like,
what is this? Like this doesn't feel like a date anymore.
And the person I was on a date, which said, oh,
this just makes the bill easier when it comes like,
(02:25):
kind of laughed it off. So immediately I was a
little turned off by it because I thought, how could
someone be that worried about a bill within five minutes
of being together, yet you asked me to go to
a fairly nice restaurant, Like, what is going on? What
is the vibe here?
Speaker 2 (02:44):
Is this? Is this even a date? Do you just
want a friend? Like? What is this?
Speaker 1 (02:48):
Because I got the vibe you were kind of into me,
but now I'm feeling like maybe you're not.
Speaker 2 (02:54):
So I thought it was super weird.
Speaker 1 (02:56):
It wasn't even at the end of the meal, which
is also in my opinion, and a little odd to say,
will you split the bill with me if you're being
asked on a date? So it just created this super
strange environment. And then what was really weird is for
the rest of the date, it was like it was
like a date, Like this person was trying to be
flirty and was very complimentary and seemed clearly very interested
(03:17):
in me. And then the end of the dinner comes
and the server brings over the two bills, and I
looked over and this person didn't tip very well at all,
which to me is also a deal breaker, like give
a good tip to a server they work so hard.
It is not an easy job, like tip somebody, well
twenty percent minimum for server. Come on, I mean you
(03:40):
just have to. But that's a whole other time we talk,
I guess. So then we pay and this person says,
can I walk you, you know, to wherever you're going next?
Because I made it clear I had plans after, and
I said, oh, you know what.
Speaker 2 (03:53):
I'm good. I'm good. I'm just kind of in a rush.
I'm gonna do a phone call after.
Speaker 1 (03:57):
And they were super insistent, like come on, like, let
me just want I'm not ready for the night to end.
Let me just walk you. Let me just walk you.
And I literally was like what do I say now?
Speaker 2 (04:05):
Now? This is just awkward.
Speaker 1 (04:07):
So I let the person walk me to know the
subway and then they were like, I really hope we.
Speaker 2 (04:11):
Can do this again again.
Speaker 1 (04:13):
I can't even say it right because it was so
it was so weird, and I just remember thinking like,
I will not be calling you. This is totally strange vibes.
And I kind of like hurriedly went down the subway
steps after dodging what I thought was like a kiss
and coming. I'm like, no, no, we're not playing that game.
So get on the subway and go. And this story
(04:36):
got me thinking, is it a deal breaker for you
if somebody wants to split the bill with you on
a first date? And I guess there's a few different caveats, right, Like, listen,
we're in twenty twenty five. I am all for a
quality for all my ladies listening, for all of my
gay men listening, Like if you were like, I don't
need to be bought. I want to be seen as
an equal. I don't need someone to pay for my meal.
(04:59):
Power to you. Yes, yes, yes, I love that. For you,
that's great. But on a first damn date, you shall
let someone take you out. I'm sorry you should. If
you are being asked to go on a date, I
think that that person is responsible for taking you out, period,
point blank. Now that doesn't mean that if you continue
(05:19):
seeing this person on date number two, you say you
got me last time, let me get you this time.
Speaker 2 (05:24):
I love that.
Speaker 1 (05:25):
I am all for a little ping pong in the
relationship like that, or in the dating ship, I should say,
But for a first date, if somebody is setting the restaurant,
which by the way, they're choosing the price point of
the restaurant. They're choosing the location. Maybe you have to
go a little further for this location. They're choosing the time.
It's like a lot on you to accommodate them and
(05:47):
leave everything up to their planning. So the least somebody
can do is pick up a tab if they want
to go out with you, if they want your time,
if they want to take up your Thursday or your
Friday night. It's very simple. Otherwise, don't ask somebody on
a date if you don't intend to take them out right.
Speaker 2 (06:06):
It's just to me.
Speaker 1 (06:07):
Maybe I don't know, maybe it's a little old school
or antiquated, but if I sit down at a table
and we are on a first date and the first
thing you say to me is let's have separate checks,
or if at the end of what I think is
a really great date you say, can we split the bill,
I'm instantly going to think you're not interested instantly, or
that I did something wrong to turn you off from.
Speaker 2 (06:29):
The date, or that you're cheap, which.
Speaker 1 (06:32):
To me is not great because you know, you don't
need to be extravagant, but you also don't want to
come off as like super cheap. That's not fun. So
it just sends the wrong message as well. It's a
very very confusing thing. I think that in this day
and age also a lot of people feel like there's
(06:53):
mixed signals when it comes to dating.
Speaker 2 (06:55):
Right.
Speaker 1 (06:55):
You don't know if someone is super interested in you, you
don't know if they're not. There's a lot of options
are online dating, going on four dates a week. So
if you're really digging someone, as the person who asks
somebody out, show them, like show them by a simple
gesture of covering their tacos and a margarita. That's it,
very very very simple. I think dating is such an
interesting thing, and I think that there's a lot of
(07:16):
people who kind of form these rules in their mind
about dating that really come from nowhere, but then they
stick to them. And I do have a friend who
said on a lot of first dates they always go
in on halves for the bill, and I thought why,
Like I don't understand that. Why And they're like, well,
I don't know if I want to see this person again,
or I don't know if it's going to lead to anything.
So why am I going to waste my money on
(07:37):
somebody if I don't intend or if I don't know
if there'll be anything else with this person, Like I
don't know if they'll say yes to another date with me,
or I don't know if I'm going to want to
go on another date with them if I meet someone else,
And all of that I understand. But it's the game
of dating. It's the price of dating, right. You got
to get in the arena to see what can happen.
If potentially meeting the love of your life means spending
(07:59):
an extra forty bucks on a dinner, then I think
it's worth it. I think it's worth it. And if
you're choosing to go on dates with different people five
nights a week, well that's your decision, bro, Like, that's
up to you.
Speaker 2 (08:10):
You're choosing.
Speaker 1 (08:11):
That doesn't mean that you should make all of these
people you're asking out split the bill. I am so
gung ho on. If you ask somebody out, you need
to pay the bill, period. And I think money's a
really interesting topic in general, especially between friendships and like
should you talk about money?
Speaker 2 (08:27):
Should you not? What do you do when bills come?
Speaker 1 (08:31):
When you're in a group of friends and one friend
got the eighty dollars stake and you got a fifteen
dollars taco Like, that's all different. That's different. That's for
another Tommy talk. There's a lot of Tommy talks that
can come from this, but I am specifically talking about
a one on one date. You ask somebody out, you
take them out. It's very simple to me. I also
think that when you do go on that first date,
(08:54):
there's a lot of a lot of emotion to navigate, right.
You're like, in the we're getting to know you phase,
you're trying to share things about yourself but also seem.
Speaker 2 (09:05):
Not overly open or.
Speaker 1 (09:11):
Crazy or emotional or all the things right, because you're like,
oh my god, I want this person to maybe like me.
So the least that you can do is take the
money out of it, take the money out of the conversation, Like,
just don't make it a thing, pay the bill, have
a great net. If you don't want to see the
person again, fine, it's the price of dating, and move on.
(09:31):
But let me tell you if almost single people out there,
what you don't want to do is sit down at
a restaurant and tell the server to give you separate
checks upon sitting down, because you will not ever, ever
ever date that person again.
Speaker 2 (09:46):
If you are interested in them.
Speaker 1 (09:47):
It is the number one way to run out the door.
I should have run out the door. There were those
little bells on the door, and I should have had
those bells ringing because I was like, why the hell
am I still here. I did not have enough alcohol
at that dinner to get through it, but you know what,
I made it out alive. And you got to go
through some rough dates to meet the right one. And
I am so happy I have met my right one
(10:10):
because there's never been anything like that with this person
in my life.
Speaker 2 (10:15):
Right now.
Speaker 1 (10:15):
My husband has been nothing but wonderful and generous and kind,
and so have I. And like I said, it should
be reciprocal. But a first date, Come on, guys, Come On, guys.
By the Damn Tacos and the Vaka Soda. I've Never
Said This Before is hosted by Me Tommy Dedario. This
podcast is executive produced by Andrew Piglisi at iHeartRadio and
(10:37):
by Me Tommy, with editing by Joshua Colaudney. I've Never
Said This Before is part of the Elvis Duran podcast
network on iHeart Podcasts. For more, rate review and subscribe
to our show. And if you like this episode, tell
your friends. Until next time, I'm Tommy de Dario
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