All Episodes

April 10, 2025 19 mins

We take a deep dive into regrets that have shaped our lives, exploring the moments that haunt us and the lessons they've taught us along the way. From financial missteps to spending too much time on other people, we share personal stories about the experiences we wish we could do over.

• Weekly What If: Could you erase one moment in your life if you'd lose all the lessons from it?
• Financial regrets and the power of teaching the next generation to start saving early
• The cost of caring too much about what others think and spending years seeking validation
• Friendships we held onto too long versus ones we wish we hadn't let go
• The science behind gut feelings and why our bodies know the right choice before our minds do
• This or That: Would you rather regret posting something or not posting when you had the chance?
• Hot takes on regrets including "People who say they have no regrets are lying or insufferable"

Tell us about your biggest regret, or something you didn't mind doing but the consequences were worse than expected. We want the real talk - that's why we're doing this podcast. Zero chill.


Send us a text

Thanks for hanging out with us on Brother Sister Whatever, your no-BS guide through the messy middle!
If this episode made you laugh, cringe, or question your entire existence as a GenX/Xennial — please hit subscribe and leave a review. It genuinely helps more unhinged humans find their people.

Keep the Real Talk going:
➡️ Follow @brothersisterwhatever on YouTube for video episodes, Instagram for Reels & rants, and Facebook for community!
📧 realtalkzerochill@gmail.com
🌐 www.brothersisterwhatever.com

🗓 New episodes every other Thursday.
Bring your feelings. We’ll bring ours.

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Okay, welcome back to Brother, Sister.
Whatever, today's episode isall about regrets the ones that
haunt us, the ones we laughabout now and the ones we
pretend don't exist.

Speaker 2 (00:11):
We know you have some guys.

Speaker 1 (00:13):
I have plenty.
I could do this episode soloand carry it.
Let's start with the weeklywhat if?

Speaker 2 (00:20):
Let's do it Weekly.
What if let's do it Weekly?
What?

Speaker 1 (00:23):
if Okay, so what if you could erase one moment in
your life, but you'd lose allthe lessons that came from it?

Speaker 2 (00:32):
Oof.

Speaker 1 (00:33):
Right.

Speaker 2 (00:34):
Yeah, that one's tough, that's tough yeah.

Speaker 1 (00:38):
Do you want me to start while you think?

Speaker 2 (00:40):
Sure.

Speaker 1 (00:44):
Okay, here's the thing I don't regret Much.
Because I appreciate all thelessons that came out of it,
even though they were tough atthe time.

Speaker 2 (00:51):
Yeah Well, I think that's you growing.

Speaker 1 (00:54):
Well, yeah, I think every decision you make leads
you somewhere, in some way downa growth path.

Speaker 2 (01:01):
Yeah, but a lot of people don't look at it like
that, you know Well, yeah, so Ithink that that alone speaks a
lot.
You know, I actually think it'svery like taboo's not the right
word, but it was almost likefailure had to be avoided at all

(01:25):
costs and a lot of people wereprogrammed like that and it's
only been, maybe like what thepast 10 years, where you hear
about it way more now, whereit's like failure is what got me
to where I am.
Failure is this Failure?
Is that, like now, we're happyabout failure, right?

Speaker 1 (01:47):
Yeah, In a way it's true.

Speaker 2 (01:49):
So to say what have you failed at, like, what could
you take away?
You know, saying that to peoplelike us who know what failure
does for us, I think that'sthat's really tough.
So I guess I would say for meum is there's a couple of

(02:13):
scenarios in the back of my mindwhere I wouldn't mind getting
rid of because it didn't teachme anything.
But hear me out, it didn'tteach me anything because I
didn't have that mindset,because you still need to take
something away from that.
Well, you still need to take itaway, right, that's true.
So I could basically say that Icould have done without my

(02:36):
first relationship.
That one was a real toxic one,my first, first ever
relationship.
It was in high school and like,if I could go back in time, I
would just completely remove it.
And I would completely removeit because I didn't learn
anything moving forward.
You know, and maybe it's even asubconscious thing, like, even

(02:58):
though I'm saying I didn't learnanything, maybe I, maybe I did,
but I'm're not making theconnections, or something.
Maybe, but I don't think so I'mpretty sure I was completely out
to lunch.

Speaker 1 (03:11):
Okay.

Speaker 2 (03:12):
So I'd say that that's probably the one I would
erase if I could.

Speaker 1 (03:17):
Okay, so yeah, weekly .
What if that's a pretty goodone, that's a really good one,
yeah.

Speaker 2 (03:20):
Yeah, that's a really good one.

Speaker 1 (03:23):
Yeah, I'm going to start us off by saying that I
think one of the biggest regretsthat I have is not being better
financially, not just, but notknowing.
Do you know what I mean?
And kind of you know whenyou're younger and you're like I
have plenty of time, yeah, meanand and kind of you know when

(03:47):
you're younger and you're like Ihave plenty of time, yeah, and
then you literally blink youreyes and you're in your 40s and
your life is over.
No, I'm kidding and you're likeoh shit, I'm not as far into my
rsps as I should be, or you haversps shit.
So biggest regret definitely Iwish I had been smarter.
Even just $20 a month, justsomething.

Speaker 2 (04:13):
It's not over though.

Speaker 1 (04:14):
No, it's not.

Speaker 2 (04:16):
But yeah.

Speaker 1 (04:17):
But think of how far, much closer I could be to my
goal if I had started young,closer I could be to my goal if
I had started young.
So, but that regret is going tolead me to teach my kids how to
do it better.

Speaker 2 (04:30):
For sure.

Speaker 1 (04:31):
You know, think about those things.
It's never too fucking early.
That's my for sure.
My top one, one of my topregrets over the years.
I know what about you.

Speaker 2 (04:44):
Well, you know, I know it's cliche to be like, you
know I have no regrets and brr,brr, brr, brr.
But if I had to pick a regret,I would say you know that,
probably say my biggest regretis spending too much time on
other people.
You know, I'd say that that'sprobably my biggest regret.

(05:05):
Not, you know, I mean if, if Ihad to like accumulate it in
like a sense of like years oflife, it's probably half my life
.
You know what I mean, just ingeneral, right.
So I think, um, you know thatthat's probably a big regret.
You know, caring about whatthey think, whether it's trying

(05:29):
to, you know, get validation outof them, you know, whatever it
is, it's about the focus onothers as opposed to yourself.
You know that would be probablya big regret.

Speaker 1 (05:41):
Yeah.

Speaker 2 (05:42):
You know, you live and learn.
But yeah, that's how it worksright, yep For sure.

Speaker 1 (05:47):
Boundaries why, like I'm just discovering what real
boundaries look like at thisstage of my life, imagine if I
had really discovered that.

Speaker 2 (06:01):
Yeah.

Speaker 1 (06:02):
When I was younger, in my 20s especially, oh my god
yeah, yeah, same.

Speaker 2 (06:08):
Well, I mean, you know we're siblings, right,
we're not identical, but clearlythere's certain things that are
the same yeah, or relativelyyeah, so yeah, I'm in the same
boat yeah, that's crazy.

Speaker 1 (06:22):
What about relationships?

Speaker 2 (06:24):
Like in what way?

Speaker 1 (06:26):
Friendships, romantic relationships.
Are there any regrets there?
Half the people that I dated Iwould not have dated.

Speaker 2 (06:33):
Well, I mean our weekly.
What if was me saying my firstrelationship?

Speaker 1 (06:39):
Oh, that's true.

Speaker 2 (06:40):
So I'd say that, yeah , for sure, that's definitely a
big thing there for me for sure.

Speaker 1 (06:45):
Yeah, I think there are some.
I don't think I can sayanything about friendships,
though I don't have anythingthat stands out to me.

Speaker 2 (06:53):
I could say a couple things about friendship, I think
.
I think that there's definitelysome regret there in
friendships Friendships that youknow, I wish I didn't hold on
to, and then friendships I wishI held on to, kind of thing.

Speaker 1 (07:12):
Which one stings worse?

Speaker 2 (07:16):
Which one stings worse?

Speaker 1 (07:17):
Yeah.

Speaker 2 (07:18):
That's a good one, I think, the ones that I held on
to longer than I should have.
And so the reason why I wouldpick that over the other one is
because I think in my mind ofthe regret of people that I wish
I stuck around with.
I think the lesson that Ilearned from that is that, and

(07:45):
because whether it was me orthem that said like okay, fuck
off.
Kind of thing.
I think it was meant to be inthe sense that if it was a true
friend, they would haveunderstood you or you would have
understood them, and hence thatwould have never happened,
regardless of what your actionswere that maybe have caused that

(08:06):
friendship to crumble.
So the reason why I pick theother one is because the other
one is much more of a lesson inthe sense of like, uh-uh, like
when I'm done, I'm done, kind ofthing, and I need to end that
charade right then and there.

(08:27):
So to me that's why that one ismore important.

Speaker 1 (08:31):
See, when I look back on past relationships or
friendships, for me it's the oneit stings.
You always think about the onethat got away, right, you always
think it's almost like a FOMOof regrets, right, when you
think about it, fomo, you likeyou, you, you don't know what

(08:54):
you're missing out on.
There's so many possibilities,but the one that you, you waited
too long maybe to to get rid ofthere's, there's nothing else.
You can't milk that cow anymore than you milked it.
Right, it is what it is.

Speaker 2 (09:10):
But yeah, and it makes you think of other things
though Like if you didn't waitas long as you did, then maybe
that connection or friend orwhatever that you had in the
interim, but now it's not there,right, like there's so many
scenarios.

Speaker 1 (09:27):
It all depends on how you look on it and what makes
the most impact for you.
Do you have any regrets aboutnot listening to your gut?
Specifically, yeah.
And it could be waiting toolong, right, yeah, to add
something, or whatever I willtell you something though.
Okay, what that I?

Speaker 2 (09:45):
know now that I know now, and if you don't know this,
I mean you should be.
You know, you should get thisinto your head, right?

Speaker 1 (09:55):
now.

Speaker 2 (09:56):
Okay, I'm probably going to botch the study.
Okay, like I'm going to botchit, but I'm going to explain,
just like, my logic behind it ofhow it went down.
Okay, they did a study on yourgut feeling.

Speaker 1 (10:14):
Okay.

Speaker 2 (10:14):
Okay, and like you making a choice, kind of thing
All right, okay.
And I'll explain to you whatthey did.
They had cards red, blue andyellow Okay.
Do you know this story?
No, okay, okay.
And so each one had a value,and the point of the game was
that you have to get the highestvalue out of a certain amount

(10:35):
of cards.
Like, you get 50 cards, okay,and so you get to pick.
You get to pick red, yellow,you know.
And so what they didn't knowwas that, believe it or not,
each stack, like the blue onesones, was like the highest pot
of, like a ratio like, let'sjust say, 75 to 100 okay and

(10:56):
then the yellow cards were 25 to50 and then the blue, the.
The last cards were like 1 to 25, in the sense of like a numeric
number okay, like let's say,it's cash, okay, and so you
would pick one, so I would pick.
Like the yellow.
It would be like a fouricnumber, okay, like, let's say,
it's cash, okay, and so youwould pick one, so I would pick.
Like the yellow.
It would be like a four right,and so you're picking the cards,
you know, and obviously aroundcard 35 or 25 or whatever,

(11:21):
everyone was a little different.
But around the 25, 35, theystarted realizing like holy shit
, okay, the blue ones have thehighest pot.
And so clearly, everyone justkept picking the blue card
because it was the highest oneright yeah.
Now here's the thing.
This was all recorded.

(11:41):
Obviously you know everythingthey were doing.
The body reacted on card numberfive and started subconsciously
.
They started taking the, thehigher pot cards more frequently
before they caught on and theywere clearly like blue, blue,
blue blue but listening to theirgut yeah, but their gut, at

(12:01):
card five, they, they almostwere drawn more to taking the
blue card, so they didn't takeit every time because they
didn't know consciously.
So they were still like, oh,maybe I'll get lucky with the
yellow, you know, you know, orwhatever.
But by card five the body wasalready the gut, was already

(12:22):
taking that higher pot card andso, needless to say, the moral
of this little story here isthat your body already knew on
card five that that was thehigher pot, and so the point is
that you got to follow that gut.
And when I heard that storyobviously it was said a lot

(12:45):
better than what I just did, buthearing that story I was like,
wow, like it makes so much sensebecause there's been so many
times where I was like why thefuck didn't I listen to what I
was thinking, you know, orwhatever, and like now I
actually try to be veryconscious of my gut, and so

(13:11):
that's kind of what I've beendoing now.
So if my gut says it's like,okay, I go with it.
You know, versus like you getthe gut, and then you're kind of
like, oh, now I do it onpurpose.
The moment I feel the gut, I gowith it, I throw the cards in,
you know, or whatever, and it'sbeen working.

Speaker 1 (13:31):
So yeah, it's interesting that you say that,
because siblings maybe you feelthe same way here is.
For a long time I didn't allowmyself to even think about
something.
I was so impulsive that Ididn't even have enough time to

(13:54):
allow my body to even have thatinstinct or that intuition.
Do you ever feel like you'vegone through?

Speaker 2 (14:04):
periods like that in your life.
You mean like when we wereteens.
Teens and 20s for sure In my20s.

Speaker 1 (14:09):
Yeah, it's so interesting because those are
the times.
Those are the years in which Ihave the most regrets.
My regrets have gotten a lotless as I've gotten older.
Right, because I choose tolisten now more to my gut.

(14:30):
I choose to pause and reallythink about things, as opposed
to just yeah.

Speaker 2 (14:34):
Right yeah.

Speaker 1 (14:35):
It's interesting.

Speaker 2 (14:36):
It is interesting.
It is yeah, okay, it's good.

Speaker 1 (14:40):
Yeah.

Speaker 2 (14:42):
All right, this or that.

Speaker 1 (14:43):
Okay, yes, this or that.

Speaker 2 (14:46):
All right, you starting or me.

Speaker 1 (14:48):
You go.

Speaker 2 (14:50):
Okay, how about this Regret posting it or regret not
posting it when you had a chance?

Speaker 1 (14:56):
I'll probably regret posting it.

Speaker 2 (14:59):
Regret posting it.
Yeah, okay.

Speaker 1 (15:03):
Regret saying I love you too soon, or regret never
saying it at all too soon, orregret never saying it at all
Too soon, yeah, yeah, I've neverbeen in a situation where I've
never said it like or that I'veregretted not saying it.

Speaker 2 (15:18):
Yeah yeah, it's always been too soon.
Yeah, yeah, ooh.
Regret what you said out loudor regret what you kept to
yourself.

Speaker 1 (15:27):
Always regret what I kept to myself.
Hands down.

Speaker 2 (15:30):
Same.

Speaker 1 (15:31):
I never speak up enough.

Speaker 2 (15:33):
Yeah.

Speaker 1 (15:33):
So that's yeah Same.

Speaker 2 (15:37):
Oh yeah.

Speaker 1 (15:37):
Yeah, regret ghosting someone, or regret giving them
another chance.

Speaker 2 (15:43):
Shit, that one's tough, I'm gonna say regret
ghosting them Really.
Yeah, how come?
Because by the time, because Idon't do that, so because by the
time I'm ready to ghost them.
I gave them so many fuckingchances, or wait.

Speaker 1 (16:03):
Actually, it would be the other way.
Yeah, sorry I'm giving them toomany chances, exactly.

Speaker 2 (16:06):
Okay, that's what I meant.

Speaker 1 (16:08):
I'm with you because, for the exact same reason.
Yeah, I'm, like you know, theperson kicking the dead horse in
the corner there.
Yeah, one more chance.

Speaker 2 (16:15):
Yeah, yeah, that's me Regretting regret trusting
someone too fast, or regretnever trusting them at all.

Speaker 1 (16:25):
Definitely regret trusting somebody too fast.

Speaker 2 (16:28):
Okay, yeah Same.

Speaker 1 (16:30):
Yeah, regret a job you didn't take, or regret the
job you stayed in too long.

Speaker 2 (16:38):
I've never really had that yeah.
That one's a tough one for me.
So I guess I'm going to sayregret the job that I didn't
take, like if I had to.

Speaker 1 (16:50):
Okay, had to okay you know, for me it's the opposite.
I've never turned down a job.
Do you know what I mean?
Like it's always been theopportunity that I've seeked,
and so, therefore, if I'vereceived it, then I took it.
So it's always stayingsomewhere too long, but that's
like a standard throughout allthe aspects of my life regret

(17:11):
something that you did drunk, orregret something you didn't do
because you were too sober.

Speaker 2 (17:17):
Oh, 100% the first one there Regret something I did
when I was drunk.

Speaker 1 (17:20):
Drunk I know 100%, it's so bad.

Speaker 2 (17:24):
All right people.
So now we are going to do someof those hot takes, let's go.
So here we go.
Your gut was right, you justdidn't listen again.

Speaker 1 (17:35):
Yeah, hands down, I bow to that one.
You don't learn from yourmistakes, you just learn to
regret them quieter.

Speaker 2 (17:45):
That's a good one.
Yeah, people who say they haveno regrets are lying or
insufferable.
Insufferable People that don'thave any regrets, like fuck off.
You're just being defensivebecause you said that before,
that you have no regrets.

Speaker 1 (18:05):
Maybe no.

Speaker 2 (18:08):
I didn't say I didn't have no regrets.
You did, for you technicallydid.

Speaker 1 (18:11):
Well, but it was with a clause.

Speaker 2 (18:13):
I know I'm just messing with you.
You're messing with me.

Speaker 1 (18:17):
If it didn't result in emotional damage?
Was it even a real mistake?
What did we say about trauma?

Speaker 2 (18:25):
Yeah, seriously, sometimes the right decision
still comes with regret, andthat's wild.

Speaker 1 (18:32):
Last one.
I don't regret the decision, Iregret the consequences.

Speaker 2 (18:40):
Yeah, yeah, that's a good one too, that is a good one
.

Speaker 1 (18:43):
That's a good one to end up.
Like to end the episode with.

Speaker 2 (18:48):
Yeah.

Speaker 1 (18:48):
Why don't you guys write your biggest regret, or
one that you actually didn'tmind doing, but the consequences
were worse?

Speaker 2 (19:00):
And don't sugarcoat it.
We want to hear the real talk.

Speaker 1 (19:05):
Yes.

Speaker 2 (19:06):
Okay, that's why we're doing this podcast, yeah.

Speaker 1 (19:08):
Real talk Zero chill.

Speaker 2 (19:10):
Exactly All right, so we want the serious comments.

Speaker 1 (19:15):
We want the goods.
All right, All right guys.

Speaker 2 (19:18):
We are going to take off.
This is brother, sister,whatever.

Speaker 1 (19:22):
Bye guys, bye, see you next week.
Advertise With Us

Popular Podcasts

Crime Junkie

Crime Junkie

Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

24/7 News: The Latest

24/7 News: The Latest

The latest news in 4 minutes updated every hour, every day.

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.