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September 1, 2025 24 mins

Casi wrote into “Ask Amy and T.J.” in their latest Yahoo relationship advice column, wondering if she should give a man 25 years older than her another try, now that she’s older and wiser. She met him when she was a freshman in college and he was in his 40s… Now she’s about to turn 40 herself and thinks they may be ready for love. 

 

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:02):
Hey, if folks, sit is Monday, September first, and age
a nutting but a number when it comes to dating.
But what if she is an eighteen year old freshman?
Because age still matter if the gap is twenty five years?
But oh, the story gets oh so much more complicated

(00:23):
than that. And with that, welcome to this relationship edition
of Amy and TJ. We're going over Robes, a question
that a reader sent into us on our yahoo dot
com column asking for some advice. You can find it
yahoo dot com, a new one every week in the
life section. Let's start with that, Robes, there is an
age gap here twenty five years. Now. When you first

(00:47):
hear that, is that a big deal?

Speaker 2 (00:49):
Oh, it's a pretty big deal. I mean that's a
parent to child generational gap.

Speaker 1 (00:53):
Okay, so you would have a follow up question immediately, Hey,
thinking about dating somebody he's twenty five years older? Your
first question question, you need to know how old the
woman is right now? Right?

Speaker 2 (01:03):
Yes, one hundred percent, Because well, there's already going to
be a literally a generation gap between the two of you.
But if you've lived enough life where you can go
into that relationship with enough experience, you won't obviously ever
catch up with your partner, but you've had enough life

(01:24):
experience that you can navigate your way through it potentially successfully.
If you're young, if you've just started off in life,
if you've just left your parents home, it's like you
just went from your dad to your boyfriend. Like it's
almost as if you are still seeking that same sort
of relationship where you've got that dynamic where someone is

(01:46):
a parental figure to you, because how could he not.

Speaker 1 (01:48):
Bekay, it's hard to endorse, is it not at that age?

Speaker 2 (01:52):
No?

Speaker 1 (01:52):
Okay, details are different, and there are a lot of
people out there with age gaps in their relationships. But
it's a hard I would say, as I'm looking at
it a couple of different ways. It's hard as a
parent especially, but it's hard to endorse a relationship when
somebody is seventeen, eighteen, nineteen, twenty, even up to twenty five,
and somebody has a twenty five year age gap. It

(02:14):
can work, People can fall in love, that's from the outside.
When it's somebody you care about, a family member, especially
a kid. If somebody you love a child, it's difficult
to stomach.

Speaker 2 (02:29):
Frankly, I think it's very hard, and yes, there are
plenty of examples of successful relationships where they've met in
their early twenties and he's twenty years older and they're
still together to the end. So I would never say
it couldn't happen. But yes, my daughters who are nineteen
and twenty two, I would not want them to date
out of their decade basically up until they're thirty period.

Speaker 1 (02:53):
Okay, So we mentioned all this, folks, because we had
a young lady writ into us Carrie Cassie. Excuse me,
Cassie wrote in Now, yes, there's an age gap, she
wrote in and asked us about. But I have kind
of been messing with you all because there's another very
significant detail to this story that needs to be added
before you kind of just come to a conclusion. This
isn't just a simple hey, there's an age gap? Should

(03:16):
we date? No? No, no, no, no. There is much
more to this.

Speaker 2 (03:19):
One wrote Yes. Here is the actual question or letter
that was written into us Amy and TJ. When I
was a freshman in college, I fell in love with
a man twenty five years older than me. The connection
was unshakable, but I was young and he was newly divorced.
Co parenting eight kids. It didn't work. It's been thirteen years.

(03:42):
I'm about to turn forty, and he stepped back into
my life. I think we've both grown a lot and
might be ready for a real relationship. He worries that
my parents and my friends won't approve, but I don't
want to crowdsource my relationship. If we try again, will
it be the same old story or could it be
for real this time? Cassie.

Speaker 1 (04:05):
Now, folks didn't see, but I wish they could have
seen you at a particular moment as you were reading this,
you stopped, you made a little face, you looked up
at me, you scratched your notes. You had a whole thing.
And the line was I was young. He was newly divorced,
co parenting eight kids.

Speaker 2 (04:25):
That's a huge twist in the story. The twist is,
yes they had or he had eight kids, but that
now they want to try again. And now she's older,
Now she's pushing forty. He's in his sixties. I guess
his children have been raised. She's lived a lot of

(04:47):
her life. So my advice to her was to go
for it, yes, but to really you know, obviously, she
has to ask herself if she wants kids. At this point,
it's kind of do or die. At the age she's at,
she has to kind of that ship is either sailed.
I'm guessing he probably is not too into having more
kids if he already has eight. I can't even that guy,

(05:08):
can't even give my head around that. But yeah, So
as long as she has come to peace with the
fact that she doesn't want any more kids and she's
okay being a step mother figure ish even though she's
probably a peer in terms of age to his kids, Like,
as long as she's gotten all that space in her

(05:29):
head figured out, I don't see the harm. She's lived
enough of her life at late thirties, she can make
a grown up decision.

Speaker 1 (05:38):
What problems do you have then? You don't have that?
She can make this decision now, but not then. My
question is so much of my advice, if you will,
was based on I need to understand a dynamic that
what forty three year old man is pursuing and has
fallen in love with and think his life and his

(06:01):
future is with an eighteen year old freshman in college.
I need that answer before I move to the next thing,
because I'm trying to understand where his head is and
where in his life he places an eighteen year old
freshman sweetheart. He clear he probably has kids her age.

Speaker 2 (06:21):
Oh, I'm sure he does.

Speaker 1 (06:23):
Where that dynamic I'm trying to understand how do we
go from that to this? A lot of things have
happened in both of their lives in those years, but
I needed to understand and I want to desperately understand
that initial dynamic. Does it matter? And I might be
not looking at this the right way? Ropes, What doesn't matter?
How it was then, this is now? She's a grown

(06:45):
ass woman. He is now sixty early sixties.

Speaker 2 (06:48):
Yeah, I mean for her to want to be with
someone like that, I would also obviously she I'm sure
can do the math. And it's one thing for someone
to be in their sixties, but ma'am, when you get
into your seventies and your eighties, it's a big difference.
And if you're in your forties or your fifties, like
obviously that's the age we're in right now. We're very active,
We're very we you know, can run have marathons and
climb mountains and go all day shopping, and you know,

(07:10):
you start choosing to go through life with someone who
is twenty five years older than you. While it didn't
seem like a big deal, funny enough in terms of
vitality and just probably energy when she was in her
early twenties and he was in her forties, that actually
probably felt pretty normal and pretty similar. It's now, Yes,

(07:31):
you might be more mature as if as a woman,
and be able to make a better decision, but now
you're gonna be dealing with other issues, physical issues that
maybe you aren't prepared for. There's just a lot to
think about. And look, plenty of these relationships have been successful.
I know people who have age gaps like this and
they're they're just soulmates and it's okay. So I would

(07:52):
never I don't discourage her from seeking it out. I
can only imagine she's gone through and figured out all
the rest. My issue was being worried. He's worried about
her friends and her family not approving. I think that
should be the last on her list of things to
be considering.

Speaker 1 (08:10):
I'm with you one hundred percent. And this thing she
wrote in here is the crowdsourcing. What was her line here.

Speaker 2 (08:16):
About she doesn't want to crowdsource her relationship? Basically, you know, yes,
let other people have an impact on what she does
or doesn't do.

Speaker 1 (08:26):
And they should and you are ultimately responsible. But I
hate using the word crowdsource because it sounds negative, like
I'm gonna put it in somebody else's hands. No, anything
you do in your life that's that important, you should
absolutely get counsel. You should go to the people that
you love most and the people that love you most,
and they're going to give you good counsel. Don't please,

(08:48):
I encourage everybody. Don't label anything as crowdsourcing or thinking
you're giving somebody outside of your relationships or input in it. Yes,
they should listen to them, listen to it closely, and
then you make the decision. But absolutely she'd be talking
to other people. I as a as a parent, my
answer is different than a guy on the outside. It

(09:09):
would be tough robes. It just is she has to
I don't know if she has kids. It's possible she
could already, Yes, it's possible.

Speaker 2 (09:15):
She didn't mention that she had another relationship with that
she ended up having children. She did not mention that.

Speaker 1 (09:19):
Doesn't it begin in with that? At this point what
the kid question? Isn't it begin and in with that
question if she wants to have kids, it's likely he
does not. Yes, doesn't it begin in with that question?

Speaker 2 (09:31):
And she didn't bring it up, So it didn't seem
like this was an issue for her, because if it were,
I'm sure she would have brought that up in the question.
She would have said, Hey, what do you think if
I still want to have kids, should I be willing
to throw away my shot at having or becoming a mom. No,
she didn't talk about any of that, so I actually
think because she chose not to speak about it, it's
not an issue.

Speaker 1 (09:50):
Okay, comments are starting to come in about this, and
encourage all of you all again. Go to Yahoo dot
com Life section. You'll see the article there. You can
see what other people starting to write in, and we
love and we encourage you to chime in as well
with your advice. But this robe seems so far we're

(10:11):
not going to get into it yet. Some of the
comments we've seen, but so much of a question of
simply taboo. It feels when there's an age gap in
a relationship, it's taboo for some reason. We accept it
to a certain degree when it's the man older than
the woman, but it's still this thing we haven't gotten

(10:32):
a good handle on yet. How love can look different.

Speaker 2 (10:36):
Yes, and I think a lot of it is. Look,
we're all different ages mentally. I really do believe that. Yes,
we have a physical age, Yes we know when we
all came into the world. But I think so many
of us have different energy ages, like significantly. And there
are older folks who have that youthful vitality, that younger spirit,

(10:56):
and they want to be around people younger than them
and that feels comfortable to them. And I get that.
I think I'm one of those people. I like to
be around younger folks. I tend to gravitate towards younger people.
My friends all tend to be younger than me. You're
a little younger than me. I do feel like I
have that younger energy. However, I do think like within

(11:21):
a decade that makes sense. When you're talking two decades,
twenty five years, that is a significant difference. It's again
not that it can't work, but that is a that's
just a huge, a huge change. And there it's not
even a physical because I think that's fine. Obviously, whatever
or whoever you're attracted to isn't necessarily just physical it's
emotional obviously, and it's spiritual, but there is an experience gap,

(11:45):
and there is a power dynamic. I'm curious, like you
pointed out, when she met him, if she was a
freshman in college and he was twenty five years older
than her, how did she meet him? Was it? It
could have been at a bar, it could have been
at a bookstore, but see her professor, was there some
sort of a power dynamic that played a role in

(12:06):
her relationship with him? And that's just something that she
should examine because that would be the unhealthy part of it.
If she's trying to find a father figure, if she
wants somebody to take care of her. There's nothing wrong
with wanting someone to take care of you, but it's
just a question that when you have that big of
an age gap, you have to be cognizant of and
ask yourself, why am I attracted to someone who is

(12:27):
significantly older than me with a very different experience in life?

Speaker 1 (12:32):
You know that is you just hit on exactly why.
You probably articulated it or helped me put it together
better than I can. It's at eighteen years old. My
problem with their relationship is the dynamic when she was eighteen.
What is a forty three year old man doing with
an eighteen year old child? So let's take it back

(12:54):
a year. What is a forty two year old man
doing with a seventeen year old high school senior? Go back?
And then the year was a forty one year old
man doing with a six There's no age as you
keep going back that it feels appropriate right now that
time of her life, there is nothing as a forty me.
I'm forty eight, I have nothing an eighteen year old,

(13:16):
nineteen year old twenty.

Speaker 2 (13:17):
Twenty one, forty eight, So you'd be with the twenty
three year old? How would that feel? That would be
Ava is about to turn twenty three, so that age
Ava's friends, that would be the age date her friends.

Speaker 1 (13:30):
I can't stand any of them. I can't stand being
around them. We don't have anything to dog go out.
You're fey, just kidding, love y'all, gummy, Marcus all crew.
You know I love you, But what I'm saying to
you we don't have necessarily things in common. We've done
fun things together and were going to hang out, but
we have different interests, we have different schedules we have
It just doesn't work.

Speaker 2 (13:49):
It's funny because I think about, like you, dating in
that age group, it wouldn't look inappropriate. You look young,
they look, you know, kind of ambiguous, like you don't know,
mid to late twenties. You could you could pass for
someone in their thirties, so it wouldn't raise eyebrows the
look at all, which is funny, But the difference in

(14:11):
experience and interests and likes and all of that is vast.

Speaker 1 (14:17):
Well, whoever's listening right now, if you're over the age
of thirty five, imagine dating an eighteen year old. No,
it just so when if.

Speaker 2 (14:27):
It's one thing, I was gonna sorry, I was gonna
say it's one thing to date or have a physical
relationship with them. Fine, I can see why you'd be
attracted to maybe, but to have a significant relationship where
you're saying this is my soulmate, this is who I
want to spend the rest of my life with, this
is who I want to marry. That's very different.

Speaker 1 (14:42):
And this is why I'm trying to be always mindful
and respectful of people who do have age gaps, because
it doesn't automatically mean it's a disaster or automatically mean
it was untoward or that was a problem. I just
know what it means what an eighteen year old is,
and I know what it's like to be in your forties, right,
I know those two people should not be socially out.

Speaker 2 (15:03):
I mean, it's fun to hang out with Annalys and
her friends. It's fun to hang out with am and
her friends. But that's where it begins and ends.

Speaker 1 (15:09):
It's not our dating pool. No speak about all those
kids we have in the house. This is our dating
so weird, that would be absolutely weird.

Speaker 2 (15:17):
And again, he has eight kids, So okay, you did
the math forty three. If he had eight kids at
forty three, he had kids her age period. There's no
way he had to have started having kids in his
early twenties.

Speaker 1 (15:31):
Huh. Yeah, you know what. Look, we have an opinion,
You have an opinion. Everybody seems to maybe have an opinion.
We don't have all the details, but hey, if you
want to be encouraged, look no further than the president
of France.

Speaker 2 (15:52):
Welcome back to this edition of Ask Amy and TJ,
where we had Cassie right in and ask if she
should start up a relationship she ended thirteen years ago.
There was a twenty five year age gap. She was
in her well, she was a freshman in college, so
eighteen nineteen years old, started a relationship with somebody who

(16:13):
was newly divorced, who was twenty five years older than her,
who had eight kids. So it was co parenting eight
kids with his ex wife. It didn't work out, but
now thirteen years later, she wants to know if she
should try again. He's come back into her life. She's
almost forty, and maybe the timing was wrong and the
person was right. And so our advice to Cassie was

(16:36):
slightly different. I told her to go for it. I
thought that she should proceed with caution, even with skepticism,
but why not give it a try. What if he
was and is her person and she just needed to
mature a little bit, He needed to take care of
his family for a little bit and be focused on

(16:58):
his eight kids. Now that enough time has passed, this
might be the right time, the right place, and the
right man who knows.

Speaker 1 (17:07):
Okay, I am totally on board you putting it that way.
I'm totally on board with your advice. I'm saying, why not,
Like I stop, and I caution, And maybe that is
a dad having daughters. I pump the brakes a little
bit when I hear certain things when it comes to girls.
But what you're saying makes sense, Then why not you
say something that in particular always jumps out if this

(17:29):
is your person? Like who are we? Who am I?
Who is anybody to say what? And who this person is?
And if this works and how it works and why
it works? And who are we to say? It's just
I always want to caution myself. You are very good
at that. You'll say it out loud, but you always
want to make just You don't have to judge. You

(17:52):
can hear. You can hear and listen and maybe even disagree.
But we don't always understand all the dynamics and what's
happening and what works for them might not be what
would work for me. So I think your advice is
probably the best in what you just said, then why
not give it another shot? If you think this is
your person?

Speaker 2 (18:09):
Yeah, I mean, and we have one of the biggest
examples you teased it before we went to the break
is the president of France. I mean, if you really
look into his story, it's kind of jaw dropping. I
don't know that it would fly in the United States,
But hey, I don't know. We have President Trump with
a very storied, interesting history in dating and divorces and
women and.

Speaker 1 (18:28):
All of that.

Speaker 2 (18:29):
But yeah, the story of President Macrone and his wife.
She was his teacher, was it his English teacher, history teacher?
Which one? Was it theater teacher? Okay, yes, you're right,
it was the theater teacher. But he waited until he
got out of school.

Speaker 1 (18:45):
Correct, nothing was going on, And they say when now, yeah,
but he's what's the age gap? I can't remember.

Speaker 2 (18:53):
Oh it's twenty something years.

Speaker 1 (18:54):
Is really okay, but still he the president of France
is currently married too, and has been married for quite
some time to a woman who was one of his
teachers in high school. And do I have it right, ropes,
wasn't she married with kids at the time.

Speaker 2 (19:10):
Yes, so their relationship so he she is his senior
by nearly twenty five years. This is almost exactly in
reverse the same story. And that is her name is Brigitte,
and yes, she was his high school teacher and he

(19:31):
was a student. And yeah, they said that they love
each other and they've always loved each other and they
had to wait for the right time, but they've clearly
made it through some tough times.

Speaker 1 (19:44):
We always don't. We have that tendency to question any
relationship that doesn't look a certain way. It doesn't look
the way we think it should look, it doesn't follow
along a certain trajectory that we think it should, and
that's too bad. I understand so a certain degree, but
I don't like the cynicism where we don't Why can't
we start with giving even love the benefit of the doubt?

Speaker 2 (20:07):
Yeah, no, I hear you. If you, if you look
at the story, this is pretty remarkable. Brigitte and Manuel Macrone.
So his parents found out they thought that he was
seeing her daughter, but when they found out that he
had feelings for the teacher. She was thirty nine, he

(20:27):
was fifteen, they sent him to boarding school to get
him away from her. Okay, she you're right. She had
three children and was married and they were around Emmanuel's age.
So her children were the same age as Emmanuel Macrone
and that lasted for ten years. So that's pretty remarkable.

Speaker 1 (20:48):
But wait, what lasted ten years? So?

Speaker 2 (20:51):
Oh, he was born in December of nineteen seventy seven.
That's amazing. So you're the same age. So the two
kept in touch over the years, but Brigitte was married
at the time and had three children who were around
a manual's age, and she chose to prioritize them. That
lasted ten years, so they had feelings for each other,
but they didn't act on it. So this is actually

(21:12):
almost identical to their relationship. And then they came back
revisited it, and then they decided to get married and
they've been together.

Speaker 1 (21:21):
How is it possible. No one would accept, No one
that a fifteen year old boy could have the proper instincts,
maturity experience to know what love is like or supposed
to be like with a thirty nine year old woman.
That's wild. It's no one would say, yeah, it's possible.

(21:44):
We just don't. But here they are and look at that,
and should I judge? I don't know.

Speaker 2 (21:49):
They've been married for eighteen years.

Speaker 1 (21:50):
Now, one of w which is most of the most
marriages in the eights.

Speaker 2 (21:53):
Yeah. So they got married in two thousand and seven,
and that was a year after she divorced her ex husband.
So yeah, they had that ten year period where he
went and lived his life. She kept raising her kids,
worked on her marriage, or tried at least to maybe
save her marriage. Who knows. They ended up divorcing, and
then Emmanuel and his wife ended up marrying. And we

(22:15):
did see that little incident on the plane a couple
months ago, but short of that, seems like they have
a good relationship. So who's to judge?

Speaker 1 (22:23):
What do you do? Because there are people that are
listening to us and saying, give me a freakin' break. Stop.
This is ridiculous, it's inappropriate, it doesn't work. How dare
you even? There are some like you just can't get
your head around how that's okay and why it's pop?
Do we need to get our heads around now? We
don't need to.

Speaker 2 (22:41):
I don't think we need to understand everyone's relationship, but
I think we can respect it if real you know
it just to know that we don't know, and to
know that we don't understand, and to know that it
wouldn't be something that we would be interested. But I
think we can respect it. And especially when you see
two people who seem to be in love with each other,
who work at it each and every day, it can be.
It can seem bizarre, it can seem unusual and strange.

(23:03):
But I actually did not realize how many similarities there
were between Cassie's relationship and this one is just the
genders of reverse. So you know, she could look to
President Macrone's relationship and think, you know what, it worked
for them, why couldn't it work for me?

Speaker 1 (23:20):
So Cassie, take that with you, and these are fascinating questions.
Please keep your comments coming. We are starting to collect
and see already, but we'll do another episode in which
we will we will share some of the comments that
you all have written in began to say Yahoo dot
com in the life section. Please please please comment in Cassie,
good luck to you. So still we are pulling for you.

(23:42):
These things are hard. Relationships are hard, no matter what
it looks like, doesn't robes they're soul are difficult.

Speaker 2 (23:50):
Yeah, but there's something pulling those two together and you
shouldn't ignore it because that is special, that is magical,
that doesn't happen every day. Think about it. She's lived
a ton of her life thirteen years was he, and
they still feel this pull towards one one another. So
explore it, Cassie, and hopefully you can let us know
how it goes. We appreciate it, and we appreciate you
listening to us, Thank you for listening to this episode

(24:12):
of Ask Amy and TJ. On'm Amy Robock alongside TJ Holmes.
Have a great day, Everybody,
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