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September 4, 2025 23 mins

Amy and T.J. go over the comments and advice their readers left for Casi, a nearly 40 year old woman who wants to give a failed romance with a big age gap another try! In their latest weekly Yahoo column, it was surprising and even inspiring to hear other readers talk about their successful relationships despite the taboo of having a significantly older partner.

 

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:01):
Hey there, folks. It is Thursday, September fourth, and we
have to admit we were a little surprised and taken
aback by a lot of reader's reaction to our ask
Amy and TJ Yahoo advice column for this week and
welcome to this ask Amy and TJ audition of our
Amy and TJ podcast and robes. This had to do,

(00:24):
at least the person that wrote in, had to do
with age gaps in relationships. Who knew that this was
something that really struck.

Speaker 2 (00:32):
A nerve with the right because people seem to have
very strong opinions, and oftentimes I was under the impression
and maybe this is just a sampling with people who
wrote in, but most people tend to be skeptical of
a major age gap because they're concerned about just all
the obvious things that would Relationships are hard enough, putting
a huge age gap between two folks makes it even harder.

(00:54):
So I would have thought that most people would be
discouraging this young woman, Cassie, from trying to start again
with a man who's twenty five years for senior. But
I actually read a lot of very different comments than
I was expecting, you know.

Speaker 1 (01:10):
And a lot of when you talk about age gaps.
Age gaps, you called it experience gaps or.

Speaker 2 (01:16):
Yes, right, I think it's I think that's a good
way to put it, because people are young at hard
and old souls and you can find a lot of commonalities,
but a lot of the issues arise when you have
an experience gap, and there can be a power gap.

Speaker 1 (01:29):
Then that ensues in her dynamic, We're going to read
the full question at least from our reader, but I
think most of the concern often times comes when the
gap has to do with someone who was not just younger,
but eighteen nineteen twenty dating somebody who was fifty sixty seven.
You look at that experience gap. I think if you

(01:50):
talk about it adults who are I don't know, a
thirty year old and a fifty year old or a
sixty five year old, that it feels like two adults
still making a decision.

Speaker 2 (01:59):
Once you've had a experiences enough that you can go
into a relationship with that wisdom. I think that's a
completely different conversation. And this is interesting the reader who
wrote in Cassie she did have the experience when she
was young, a freshman in college, and then after that
attempt at a relationship with a major age gap ended,

(02:20):
she's now considering restarting it thirteen years later. So now
she is almost forty, and so now she is a
bona fide grown up, and so it is different, and
so should we just go ahead and read the question
to refresh? If you all didn't remember, you didn't get
a chance to read the column. Here is what Cassie
wrote to us Amy and TJ. When I was a
freshman in college, I fell in love with a man

(02:42):
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. I love that she
didn't need to make an explanation as to why it
didn't work. It's been thirteen years. 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

(03:03):
real relationship. He worries that my parents and 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?

Speaker 1 (03:14):
Cassie, Yeah, it could be for real. I think we
ultimately gave essentially warnings right heads up about this, it's
up about that. The concern was that she was so young,
and what did they have in common at that time?
And yes, things are different now, but it was essentially
a go for it with caution, Yes, with an open
mind to what your challenges are going to be. But

(03:36):
we're grown folks. Life is too short.

Speaker 2 (03:38):
Yeah, at this point, I feel like she doesn't have
a lot to lose, in the sense that she's had
the experiences on her own, doing her own thing, and
now she's come back and maybe perhaps that connection a
lot of connections, It might be real, but it might
not be the right time, and so maybe it is now.
And I just felt like it couldn't hurt to try.

Speaker 1 (03:55):
And you again, if anybody's been listening to these, you know,
that is the one that usually goes through all of
the reader comments and the theme the first thing I
always ask you, did you get more men than women
this time?

Speaker 2 (04:07):
I definitely, you know what, I actually put a nice
mix of men and women, But still I saw a
lot of men. I actually some of them were so
similar about age gaps, all kind of saying the same thing,
expressing the same experiences that I actually kind of had
to just pick among the many men who all said

(04:27):
and felt the same thing.

Speaker 1 (04:29):
Can I ask, then, did you notice any theme that women,
I guess were less enthusiastic about age gap relationships and
about this question or was it still split?

Speaker 3 (04:41):
I think it.

Speaker 2 (04:42):
I think a lot of most people were for the
age gap. Yeah, I mean that was really that really
took me back. So I'll all jump in with and
some of these folks, I don't know if they're men
or women. Sneed Maker is one of them. I don't know,
but this is what sneed Maker said, and this was.

Speaker 3 (04:58):
One of the skeptical reas.

Speaker 2 (05:00):
If you have to seek advice, then that is a
red flag for me.

Speaker 3 (05:04):
What is the concern?

Speaker 2 (05:06):
If they are both comfortable with the age difference, both
understand and accept their roles, and see the same future
for themselves, why question it?

Speaker 1 (05:14):
Okay, I can understand two degree, but I think it's
healthy to question any relationship if be the same age.
It doesn't matter where you are. Of course, you should
have a little level of skepticism and always seek counsel
from people you trust. Maybe you don't write into Yahoo
dot com, But I think it's always good to seek
some counsel.

Speaker 2 (05:32):
I don't know anyone who, regardless of age difference, who
isn't or who is completely sure, is completely comfortable and
how they feel and how they view their relationship. Most
people want to ask whether it's a therapist, your mom,
your best friend, your sister. Isn't that what we go

(05:53):
in because love can be blind sometimes, and sometimes people
who love us can see things more objectively, or people
who actually I don't even know us can see things
more objectively because you're not looking at things through emotion.
You're actually looking at facts versus feelings. And I do
think that it's I think it's I applaud Cassie and
other people who are willing to be vulnerable and say,

(06:13):
what do you think. I think that's healthy. But sneaed
Meeker thinks it's a red flag all right. Jane Jane
writes in and says this, I'm assuming children are not
in the picture for you. You would have stepchildren and grandchildren,
so that might work. If you still have lots of
things in common, then I say go for it. You
might have to end up taking care of him health

(06:34):
wise sooner than you had hoped for, but that can
happen in any relationship.

Speaker 3 (06:39):
I thought that was such a good point.

Speaker 1 (06:41):
That was very practical, to look at what you're like.
It had none to do with love and feeling. This
is practical. This is what your challenges. These are what
it's going to be, and you have to consider that.
And she didn't mention. I think about a forty year
old woman. Maybe she never wanted to have kids, maybe
she does have kids. Who knows.

Speaker 2 (06:56):
I feel like she would have mentioned that because that
would have been a complicating factor.

Speaker 1 (07:00):
It's a issue.

Speaker 2 (07:00):
Yeah, by the mere fact that she chose not to
even acknowledge it or talk about it, it seems like that
isn't a sticking point. I question that as well when
we were reading through it. But he does have eight
children with another woman, so there will still be lots
of family. Hopefully he's got a good relationship with them,
and hopefully they can come around to her. She didn't
really explain if that was an issue at the time.

(07:23):
Seems like it might have been the fact that she
put it in there initially that he was co parenting
eight children after being recently divorced. So they're all grown
now and potentially around the same age as her, So
you know, it's one of those things where that could
still be a big, full.

Speaker 3 (07:38):
Beautiful family.

Speaker 2 (07:39):
You don't have to give birth to children to enjoy
them and experience them and have them be a big
part of your life.

Speaker 3 (07:45):
So I thought that was really good.

Speaker 2 (07:47):
And the thing about taking care of someone, Yeah, someone
can get in an accident, someone can get sick, someone
can get cancer.

Speaker 3 (07:53):
You never know. And that's love is not about that.

Speaker 2 (07:56):
It's about knowing when you go into it that it's
about taking care of another regardless.

Speaker 1 (08:01):
And she knows she's going to have to look sixty.
He's sixty five now, it would be.

Speaker 3 (08:04):
Somewhere around there. Yeah, that would make sense.

Speaker 1 (08:06):
I mean a forty year old woman forty five, fifty
fifty plus. I mean, you keep going. And they were
very active fault. When you think about a guy in
the next ten years, he's going to be seventy five
or eighty. Fine, you can be, but generally speaking, they're
not as acting.

Speaker 2 (08:22):
No, And someone actually several people wrote in and was
actually doing the numbers game.

Speaker 3 (08:26):
So just think about it.

Speaker 2 (08:27):
When you're fifty, he's going to be seventy five. How's
that going to feel? It might feel fine when you're
forty and he's sixty five. What about when you were
sixty and he's eighty five. How's that going to feel?
Just they were just suggesting she really think about it.
I'm sure she has, but to really actually put those
numbers in front of you and say, am I okay
with this?

Speaker 1 (08:43):
And it might not matter to her anyway, But why
should that factor in? If you feel the way you feel,
that's exactly supposed to be. Oh, something's going to happen
down the road. We hear, we're now and I don't know.
The more I we've talked about this, I'm leaning more
into that area of go for it. My only hesitation
was as a parent, thinking about my daughter at eighteen

(09:07):
dating somebody that was forty three. Yeah, at the time,
I would never get over that with this guy.

Speaker 2 (09:13):
Well, especially if the guy would be your age like
that would be alarming and disturbing. But we have friends
who were in that situation and it turned out okay.
And you know how I think about Kathy Lee Gifford
and Frank Gifford. I actually got to see a little
bit of their relationship up close, and she talked a
lot about it. We would all be in the makeup
room at the Today Show, and she met him when
she was I think in her twenties and he was

(09:34):
in his fifties or forties, forties, fifties, and they had
a beautiful love story. From everything I could hear from
her and everything I saw with my own two eyes,
it was beautiful until the very end, and she was justugh.
I mean when she lost him, she was devastated. So
that was a real love story from my vantage point.

Speaker 1 (09:54):
I think from the did we or do we? If
you take out the college part of story, does it
change how you view it? Yes, it does for me too.

Speaker 3 (10:03):
Yeah.

Speaker 1 (10:04):
She just said, I'm forty and thinking about dating a
sixty three, sixty five year old guy. Okay, yeah, I
think something about the dynamic early on I was trying
to understand and it maybe it doesn't matter, but I
I just think about an eighteen year old girl.

Speaker 2 (10:15):
Yeah, no, that's and that is a big difference. So
here are now a few of the reader's comments who
shared their own experiences, which I think is really cool.

Speaker 3 (10:24):
I think that makes it feel even more.

Speaker 2 (10:27):
Personal, just the fact that other people are in her
boat or have been in her boat and are giving advice.
So Todd wrote in and said, I'm thirty five and
my girlfriend just turned fifty one. All three of her
kids just graduated college. We started seeing each other in
November of last year, and I can't tell you just
how happy we both are together. Neither of us come

(10:47):
from wealth. We both have our differences, including our politics.
It took some time for us to adjust, but it
is worth it in my eyes. We are both we
both are honest with each other, and we look forward
to seeing what the future holds. I make her happy
and she makes me happy.

Speaker 1 (11:02):
Sounds like an adult. Thank you, Todd. Yes, that's what
it's all about. It almost sounds like their situation. It's
he didn't even have to mention his aide. What difference
does it make because take out what he said there.
Everything else is kids out of college, you see each other.
It's just a relationship.

Speaker 2 (11:17):
Yeah, and even with political differences. We've had readers write
in about that and how that's tearing their relationship apart.
He's like, look, it's we had to adjust, but we're
honest with each other and we are focused on making
each other happy.

Speaker 3 (11:30):
Isn't that what it's all about?

Speaker 1 (11:32):
Well, Todd, thank you for that. But man Todd ain't
got nothing on Anita and Pete. Yeah, Jay, who also
wrote in one of them, took very very serious, heated
and even offensive issue with the advice that Robot and
I gave Cassie. You'll see which one.

Speaker 3 (12:01):
Welcome aback.

Speaker 2 (12:02):
I can't get that out of my brain. I think
it's going to happen at least once a week, but
maybe more.

Speaker 1 (12:08):
I hope more, because.

Speaker 3 (12:10):
I'm taken aback.

Speaker 1 (12:12):
You're taking it back?

Speaker 3 (12:13):
Why do I do that?

Speaker 2 (12:14):
It's funny how your brain gets into patterns and then
I can't break out of it. Now I'm going to
start stressing about it. So welcome back.

Speaker 1 (12:21):
Welcome back. Used to have an issue with backlash and
always came out as blacklash. That used to be funny too.
I hope we can bring that one back.

Speaker 2 (12:30):
I hope that one never comes out of my mouth again.
Oh my goodness. All right, welcome back to this edition
of Amy and TJ. This is our ask Amy and
TJ edition, but it's our favorite version of it because
we're talking about what you.

Speaker 3 (12:43):
The reader wrote in.

Speaker 2 (12:45):
Under the comment section to our reader who asked us
a question about what she should do, and so this
of course was Cassie asking if she should give it
a try. There's a twenty five year age gap, and
this is round two. She's now nearly forty. Should she
make it worse? Could it actually work? That's kind of
one of the bigger questions she's asking.

Speaker 1 (13:03):
No, I have a quote. Do you have an indication
of how long they dated the first time?

Speaker 2 (13:06):
Well, it must have been for a while, because some
readers actually put in this so it's funny. Everyone notices
she said she was a freshman in college when they met. Okay,
so that means say that means she's nineteen. Then she
says thirteen years later, she's almost forty. Yep, so they
must have been seeing each other for several several years.

(13:27):
It just didn't work. But it must have gone on
for quite some time. If you do the math, she
had to have been seeing him for at least seven
years or so.

Speaker 1 (13:36):
I have to say I did not initially factor that
in because all I'm thinking when she said it when
I was a freshman, I fell in love and that
was it the connection. But it didn't work. She didn't
say how long it went. Right Now, when you think
about it that way, this wasn't just an eighteen year
old girl. She might have been into her twenties. I
mean she had to have been.

Speaker 2 (13:55):
Oh if she's now almost forty and they were apart,
they were broken up so to speak, for thirteen years,
that tells you up until twenty seven, even me, Yeah,
she was with this guy.

Speaker 1 (14:07):
So to a lot of the argument being made and
the concern I certainly had, she did kind of go
through and have an adult relationship with him, not just
a kid in college.

Speaker 2 (14:19):
Yeah, but she's also had thirteen years on her own
to see what else is out there, what she wants,
who she is, and where she wants to be. So
Anita writes in my late husband was fifteen years older
than me and a very different generation. We met late
in life too. We had twenty eight years total together
when we married, and I retired within a few months.

(14:41):
I knew I had only an unknown period of time.
We had eleven years married. We really enjoyed those retirement
married years evermore, I was very, very lucky to have him.

Speaker 3 (14:53):
That makes me like, actually get emotional.

Speaker 1 (14:55):
It's beautiful, you know we're hearing. Wow, isn't this something
I'm trying to want to single out a couple? But
maybe I will coach Belichick. I have no idea what's
going on in that relationship. But when something like that
comes out, what are people The first thing, the first

(15:16):
voices you hear are the loudest ones making fun and
making comments on Twitter, trying to get followers and doing
all this stuff, trying to just attack, attack, attack, when
we have to realize there are so many other people
out there who have had wonderful experiences that don't look traditional.
What is love supposed to look like. It's supposed to

(15:37):
look like two people who fell in love in college
or right outside of college, that got married at a
beautiful ceremony, They had two kids, and they stayed together
and died in their late eighties surrounded by family. If
it doesn't look like that, you're a bad person. Nobody's
shit looks like that, does it.

Speaker 3 (15:57):
It's extremely rare.

Speaker 1 (15:59):
But we hope while we hold on to that. So
to your point of what this woman is saying, the
number of people who would have attacked Belichick, but there's
a conversation about Belichick that another group of people are
having who can relate to You're living, who are living
and not condemning because they live something that can look different.

Speaker 3 (16:17):
It's okay.

Speaker 1 (16:17):
Yeah, I know it's still taboo, right, age guys, absolutely.

Speaker 3 (16:20):
But I thought it was really cool.

Speaker 2 (16:22):
I was surprised at how many people came out, told
their stories and were in full support of her going
for it for those reasons from actually lived experiences, all right,
So Pete, Pete came out swinging. When he started out
with a little attack on TJ and me, he said,
these two don't know what they are talking about, and

(16:43):
the majority of the comments are lost in the weeds.
I married my wife when I was twenty going on
twenty one and she was thirty eight. We had a
wonderful forty one years, four months and four days together
until I lost her in February of twenty fifth. Haven't
even thought about having a date since that time. So

(17:04):
don't tell me about an age difference being a problem
in a marriage.

Speaker 1 (17:08):
That's his experience, and an emotional one.

Speaker 3 (17:11):
It sounds like he's still grieving an emotional one.

Speaker 1 (17:13):
And that's okay. And so when I you know, I'm
always about words and how we write. It's not usually
what we say is how we say it. Yeah, and okay,
he starts out, and it set me off right immediately
just say what we don't know what they're talking about,
and that's his opinion. Who knows, he's kind of tongue
in cheek and saying it. But every he's even making
the point that I was previously making his experience. Even

(17:35):
though he was taking issue with us, he had a
different experience that was positive. That doesn't mean that there
aren't warning signs or words of caution for people who
do find themselves in relationships with age gaps.

Speaker 3 (17:48):
Yes, age gaps.

Speaker 2 (17:49):
And look, you could look at our relationship and say
an interracial relationship. So the argument people make is an
experience gap, but it's also making relationships which were already
hard hard when you have things not in common like that.
So the same thing could be said about you and
me that we have such different experiences, different cultural experiences,
different reactions to things based.

Speaker 3 (18:10):
On how we look and how we were.

Speaker 2 (18:12):
Raised, And so why would you choose to be with
someone when you already have extra problems that you wouldn't
have if you just married someone who was your age,
who looked like you, who came from your same religious background,
who voted for the same president. And I get that,
but sometimes those differences are what make the relationship better

(18:34):
and sweeter and more interesting, and you learn more and
maybe you even like I don't want to compare, but
the point being, sometimes those differences can actually create a
spark that continues until the very end.

Speaker 1 (18:47):
And you know, a lot of people again not making
a direct comparison, we're not saying that, but people walking
down the street with those big age gaps sometimes might
get looks the way an interracial couple might have decades ago. Yep,
because you're looking at it's not common or it's taboo,
that shouldn't be done for different reasons or whatever reasons

(19:08):
you have to think it's wrong. But yeah, so your point,
and right, that is still I don't care who you
are anywhere you go. I don't. I'm trying to think
of some friends we know with age gaps or something. Now,
there was another couple we knew they're not together anymore,
but still they it worked. But it's always you always
think about it crosses your mind. Oh when you see
an age gap.

Speaker 2 (19:26):
And oh, people go, is he rich? Yeah, right exactly,
I totally get that, all right, an age gap with us,
that's true, that's true.

Speaker 3 (19:36):
I'm four and a half years older. Than you.

Speaker 1 (19:37):
People ask me all the time, you have to have money.

Speaker 2 (19:46):
Yeah, that's funny. All right, let's move on to our
final reader comment. And this is short but sweet, and
I actually liked what he had to say. I say, he,
I don't know.

Speaker 3 (19:57):
It's j Jay. I guess could be a sheet as well.

Speaker 2 (20:00):
My wife of twenty eight years was nineteen when I
met her, and I was a thirty eight year old divorcee.
Seems I had to learn what not to do in
a marriage to finally get it right. He's just saying
he was divorced much like this guy, and he met
someone who was nineteen. They've been together for twenty eight

(20:20):
years and the marriage has worked really, really well versus.

Speaker 3 (20:23):
His other one. Maybe she was more age appropriate. It
didn't work.

Speaker 2 (20:26):
So he's learned just from having had a you know,
I hate to say failed, but a relationship that ended
with someone who might have been his age, and he
took those lessons and it's working. So however, you figure
out what you need to do better, differently whatever to
make a relationship work. The age thing he's saying wasn't
the issue. It was perhaps even it was him having

(20:46):
to correct some behaviors.

Speaker 1 (20:49):
You think he told his ex wife, thank you for
making me a better man. I'm kidding, that's always an
obviously you didn't say that. Well, yes, to his point
thirty eight and nineteen, I bet you her parents and
folks around her raised some eyebrows and pulled her to
the side and had some conversations. You just naturally do
that by somebody that young, And that's okay. We're not
saying anti this or that, but when it comes to

(21:11):
somebody seventeen, eighteen, nineteen years old, that's different type of
an age gap.

Speaker 2 (21:16):
Yes, even my twenty two year old recently told me
she went on a third date, which is a big
deal for her, and I said, what does he do?
And she told me he was he had a profession
upstate and anyway, it just sounded old, and I was like,
please tell me how old he is. And he's like,
don't worry, mom, he's twenty three.

Speaker 3 (21:33):
But it's funny.

Speaker 2 (21:33):
I even started to go, wait, who is this man?
How old is he? Why are you seeing him? It's
just a it's a natural concern of a parent. I
have a nineteen year old, and that's okay. Can you
imagine Ifnnilie said she was dating a thirty eight year
old man.

Speaker 1 (21:45):
We'd be on the way to Colorado right now, So.

Speaker 2 (21:47):
I understand is a natural reaction, but I love hearing
these vantage, like being able to look back and say, hey,
twenty eight years later, we're still going strong. Love is love,
and it might not look the way you think it should,
but it works for us.

Speaker 1 (22:00):
And that's the only thing we're always hoot and holler about.
I do especially just try to respect and give people
a little grace for that situations. You might not agree
with it, but you don't have to attack them for
not being like you, looking like you, talking like you,
thinking like you. Yeah, it's okay, So we always really
this was one of the more interesting ones. But I
want to say thank you to the readers who have
been writing in and being vulnerable. They are sharing details

(22:23):
about their own stories that have helped in part of
the conversation robes. And this is a big one because
it has been a big deal lately Belichick in particular
YEP talking about age gaps and to see a calm,
reason and even loving conversation happening around the same topic
but just in a different environment. Now, I love it.

Speaker 2 (22:41):
Yes, sank you all yes, please. We would encourage you
to please check out Yahoo the Life section for our
Weekly Comments Comments Weekly column, and then please leave your
comments because we would love to feature them in our
next podcast with our Next Question from a Reader, which
again will be on Yahoo next Monday. In the meantime, though,

(23:04):
hope you'll have a great day at Amy Roebuck alongside TJ.

Speaker 3 (23:08):
Holmes.

Speaker 2 (23:08):
Thank you, as always for listening.
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