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June 10, 2025 19 mins

Is it ever okay to date your friends EX? Don’t ask us, in fact, just get ‘em on the phone for an Awkward Tuesday Phone Call instead!

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Speaker 1 (00:00):
All right, it's your brand new well I guess it's

(00:02):
not a second Date today, but it's your second Date
podcast with a brand new Awkward Tuesday.

Speaker 2 (00:07):
We're here, we're here, We're here.

Speaker 3 (00:10):
And we got a new episode and that's so fun.

Speaker 1 (00:13):
And I gotta say, I surprise myself even today how
quickly I changed.

Speaker 3 (00:16):
You did? You were one side on the other side,
she was just so convincing. Really, don't for you. I
would have given her whatever she wanted. She's my friend.
I mean, you're gonna understand.

Speaker 1 (00:26):
We'd love to hear what your thoughts and comments are.
Of course eat him in that comment section. And what
do we see in today Alexis?

Speaker 4 (00:33):
Yes, I saw one from Jen five ninety who said, Wow,
I've been listening to you guys since my freshman year
and now I'm a high school graduate.

Speaker 2 (00:40):
Can't wait for another four years of last with y'all
in college.

Speaker 5 (00:45):
I hope you chake so.

Speaker 3 (00:47):
Many college parties, please, I would like to go back
to some frat parties you like the dining hall. We
were trying to raise her, right, okay, Well, you know
we've been with her since she.

Speaker 2 (00:57):
Was like twelve, teaching her how to skip class.

Speaker 3 (01:00):
Yeah, so much fun in college together.

Speaker 1 (01:03):
Jen, sit back, and here's your brand new offer Tuesday
phone call.

Speaker 2 (01:09):
You always hear people say I'll do anything for my friends. Yeah,
but honestly, would you yes anything anything? Would you lie
to would judge for them under oath?

Speaker 4 (01:21):
Not under oath?

Speaker 3 (01:22):
Jeb Well, cross your fingers.

Speaker 2 (01:26):
Maybe you get away with that. Would you let them
practice tattooing on your baby's lower back? There's a cute
little tramp stamp that says made in the back seat.
That's adorable. No, okay, So there is a limit, and
one of our listeners is definitely going to push the
limits today because she needs to ask her friend a

(01:47):
very controversial question that could easily throw a wrench into
their relationship. But she has to try because if she doesn't,
she might regret it for the rest of her life. WHOA,
you're gonna hear it your brand new awkward Tuesday phone call.
It's coming up next. It's awkward.

Speaker 5 (02:06):
It's Tuesday.

Speaker 2 (02:08):
It's awkward Tuesday phone call. What are the unspoken rules
of friendship? Oh, nobody else, not those ones. That's a
different set, you know, rules like you have to hate
the same people as I do, but never tag me
in any ugly photos, you.

Speaker 3 (02:30):
Just don't post them to begin with dove. If you're
a good.

Speaker 2 (02:33):
Friend, that too. And also, before any night out, we
have to practice kissing on each other for at least
twenty minutes.

Speaker 3 (02:40):
Oh, this is why we never go out.

Speaker 2 (02:43):
With you friends do. They're just some of the sacred
rules that must never be broken. But today one of
our listeners wants to violate one of the holy laws
of friendship, and she needs our help to do it.
Her name is Monica. Monica, please tell me you're not
breaking the kissing rule.

Speaker 5 (03:02):
Isn't that the kissing rule?

Speaker 2 (03:04):
Thank god? Okay, well, we're not friends yet we were? Okay, No,
maybe by the end of this call we'll get there. Okay,
But first, let's try to help you out with your situation.
What's going on in your life that made you email
the show for help?

Speaker 5 (03:19):
Well, like you said, I do need to break an
unspoken rule.

Speaker 3 (03:24):
I'm curious about.

Speaker 6 (03:27):
This already.

Speaker 3 (03:28):
Is that unflattering picture thing? Is that what it is?

Speaker 6 (03:30):
I have a feeling it's not no.

Speaker 5 (03:32):
I want to date my friends.

Speaker 3 (03:35):
Actually, oh god, there's so many men out there. Why
they can there's ones? It's clearly not good, Why would
you want to do that?

Speaker 5 (03:45):
Well, okay, so they only am I defense, they only
dated for like a year?

Speaker 2 (03:51):
What weeks?

Speaker 4 (03:54):
Was it?

Speaker 3 (03:54):
In high school? They dated? That might be the only time.
It's like, oh that's a good Okay, it was old.

Speaker 5 (03:59):
No, okay, woke up like a year ago.

Speaker 2 (04:03):
Well time, isn't it.

Speaker 1 (04:05):
No, you don't ever date your friends at it's just
what you just you just don't.

Speaker 2 (04:11):
But if it's been forty years and you're in the
retirement home together, does it?

Speaker 3 (04:15):
I mean you're not going to be You're not gonna
be friends anymore. Yeah, you know what I mean.

Speaker 2 (04:19):
But remember this is an awkward Tuesday phone call. We're
here to help, not to judge a right, right, that's
what If that's what Monica wants to do, we need
to be there lifting her up.

Speaker 3 (04:31):
I would rather talk her out of it.

Speaker 2 (04:34):
I doubt that that's that's even possible, Monica. So tell
us why do you want to date him?

Speaker 5 (04:42):
I mean? Okay, so first of all, his name is Ben. Okay,
we just have like this, Bob, and I don't want
to just say okay because he dated my friend that
we shouldn't explore this thing.

Speaker 2 (04:55):
Care Okay, keep an open mind, brook whatever.

Speaker 1 (04:59):
You say, maybe your friend isn't that close with you, Like,
maybe it's like a friend.

Speaker 3 (05:04):
Like a coworker.

Speaker 2 (05:05):
I said, keep an open nine friendship.

Speaker 3 (05:08):
That's a positive to me in the situation. Yeah, Like
if it's not your best friend in the whole.

Speaker 5 (05:13):
Yeah, okay, Well actually we are pretty close.

Speaker 2 (05:17):
Okay about even closer possible.

Speaker 6 (05:19):
I feel like this happens in any friend group, Like
if you got along with your friends, you tend.

Speaker 3 (05:23):
To it's like a family member. You just put a
no go.

Speaker 2 (05:31):
Yeah, well we're moving forward from this. Is there something
that made you feel like this connection was possible? Like,
was there a moment that stood out to you?

Speaker 6 (05:40):
Yeah?

Speaker 5 (05:41):
I mean so we were like outside hanging out or whatever,
and while we were talking, like we had like one
of those beer ping pong things or whatever, and it
bounce of forehead and he did the dumb thing where
he like bent over and kissed the spot where it
hit to make it feel better and.

Speaker 2 (05:58):
Allow he's got healing powers.

Speaker 3 (06:01):
He made the first move.

Speaker 5 (06:03):
I mean kind of you know, it's just like.

Speaker 1 (06:05):
A bob Okay, Okay, Can I ask before we get
too far down the road, why did they break up?

Speaker 5 (06:11):
I mean, there are theories out there, but I don't
know exactly what happened, you know.

Speaker 2 (06:15):
Okay, So besides the beer pong forehead kiss that was
completely medicinal for healing purposes, has anything else happened between
you and the ex?

Speaker 5 (06:25):
I mean, we've just been texting a lot since that night.
Oh talks around the idea of us we've been hanging out.

Speaker 2 (06:33):
Okay. Does your friends know anything about this, that this
is going on?

Speaker 5 (06:39):
She does not, okay, And I mean that that's the
whole thing. That's why I want to call my friend
about this. We haven't done anything. I kind of want
to get her permission to move forward.

Speaker 3 (06:49):
I mean, not a great move, but you're doing it
in the right way. Yeah, so you should be proud
of yourselves.

Speaker 2 (06:54):
Most people wouldn't even ask permission, They would just go
right forward, wouldn't.

Speaker 3 (06:58):
Do it in the first place.

Speaker 1 (06:59):
Well, again, if you want to keep the friendship, yeah,
you know, you got.

Speaker 3 (07:03):
To decide what's more.

Speaker 6 (07:03):
Almost like if I wanted to steal from Brook, but
I asked first, like, can I take twenty bucks out
of your pocket? At some point today?

Speaker 1 (07:09):
She probably say no, But like that I asked, I
guess that's an analogy we could use.

Speaker 2 (07:16):
So do you want to give them twenty bucks or.

Speaker 1 (07:17):
No, nobody's getting you can't have.

Speaker 3 (07:22):
My exes though, to go around.

Speaker 2 (07:29):
Okay, so it's okay when you're in high school or
when you're super old, but right now you no gotcha?
So why did you reach out to our show for help?

Speaker 4 (07:40):
Like?

Speaker 2 (07:40):
What are you looking to get from us?

Speaker 1 (07:42):
Well?

Speaker 5 (07:42):
I'm terrible at confrontation. I would rather just avoid it.
But I'm really hoping it doesn't come to any confrontation.
I hope that I come up with some valid points.
You guys help me, and she's just like, sure, go
for it.

Speaker 3 (07:55):
Okay, you know what, that.

Speaker 2 (07:57):
Wouldn't be the best. If she was like disgusted with him.

Speaker 6 (07:59):
I can see it and be like, oh that guy's awful.

Speaker 5 (08:02):
Girl.

Speaker 6 (08:02):
Go ahead, you're gonna find out real quick, like I
could see it.

Speaker 3 (08:05):
Yes, I mean the vibe from her is important. How
does she feel about her ex?

Speaker 5 (08:09):
Do you know we haven't talked about him in a while.
I honestly don't know where she is with it.

Speaker 4 (08:15):
So I was going to say, usually if they don't
talk about him, I have a feeling.

Speaker 2 (08:22):
The total opposite's going to happen, and she's not only
going to okay it, she's going to be one hundred
percent supportive.

Speaker 1 (08:28):
He's never been in a friendship, have you not really.

Speaker 2 (08:34):
How this goes? When we come back and call your
friend Aaron and ask permission to date her ex boyfriend,
We're going to do it with your awkward Tuesday phone
call right after this. It's awkward.

Speaker 3 (08:45):
It's Tuesday.

Speaker 2 (08:46):
It's awkward Tuesday phone call. Cool people let their friends
date their exes, and we're about to find out if
Monica's friend is cool. Yes, I mean, I know that
it's not the popular opinion in the room right now,
but you know what, we voiced what we needed to
say that some of us aren't one hundred percent okay

(09:08):
with this question being asked of using voice that I'm
on the fence. But now we're moving on to the
help portion of this call. That's our jobs where we
give our advice on what Monica should do here. So, Brooke,
what's your add.

Speaker 3 (09:24):
To do that she's doing it the right way?

Speaker 1 (09:26):
I will say that if you're going to do it now, listen, Monica,
this is what I think you need to do, is
you need to talk your friend up does that make sense? Okay,
So you need to maybe speak on how easy it
is for her to get a man, and how charismatic
and beautiful she is, and how maybe it's not quite
as easy for you. Oh, this a strategy.

Speaker 3 (09:50):
It's kind of almost a sympathy card.

Speaker 1 (09:52):
You're playing, yeah, and that you have this really great option,
but there's one kind of hurdle with it, and you
need her support.

Speaker 2 (10:00):
Paint her with the pathetic brush. I mean, I have
no option. Okay, can you make yourself seem pathetic, Monica? Okay,
that's good, Jose what's your advice?

Speaker 6 (10:14):
And this is his distraction actually works best. So there's
another guy that she's interested in. Get her focused on
that person that he thoughts about, someone new.

Speaker 2 (10:26):
I feel like.

Speaker 1 (10:29):
Talking to himself because he's easily distracted.

Speaker 3 (10:32):
She's like, what would I do if I was?

Speaker 2 (10:34):
It's like a little magic act illusion, like, oh, look
over here, you won't see what's going on over there.
WHI I'm looking up with your ac What do you
think about that? Monica?

Speaker 5 (10:41):
That works for me? I can do that.

Speaker 2 (10:43):
Okay. So we've got a little bit of compliments, some
self deprecation, and some distraction thrown into them up as
much as you can. What's your friend's name? By the way, Monica,
her name is Erin.

Speaker 1 (10:57):
And if Erin doesn't give her blessing on this, well
used to, We'll go through and date.

Speaker 2 (11:01):
Her ex that's the question.

Speaker 5 (11:03):
I really don't think that I could. I just hope
that she sees it from my perspective and it's her
blessing your good.

Speaker 2 (11:10):
Friends, yes, and if she says no, we will come
after her herd on your that's Brooks promise. So let's die. Wow,
I'm doing there right now.

Speaker 5 (11:26):
Good luck, thank you.

Speaker 4 (11:37):
Hello, hey, hey, wait, who's this?

Speaker 5 (11:44):
It's Monica?

Speaker 4 (11:46):
Hey, wait, so what phone are you calling from. I'm
so confused. Work work? Why are you calling from your
work phone?

Speaker 5 (12:00):
No, I'm at work, girl.

Speaker 4 (12:04):
That is so weird. Just calling yourself phone next time?

Speaker 5 (12:07):
Oh my bad. I mean there's a lot on my mind.

Speaker 4 (12:11):
Okay, like what, Oh, I've a minute. I can talk
through it.

Speaker 5 (12:16):
You're so sweet. You're such a good friend.

Speaker 4 (12:19):
I know. But tell me, okay, I don't have wong,
just tell me what's up.

Speaker 5 (12:24):
Well, you remember Dylan's party the other week, right, I
mean yeah, barely, but yeah, I guess yeah. Oh well
I noticed you were talking to that like really tall guy.

Speaker 4 (12:37):
Uh yeah, little why.

Speaker 5 (12:41):
Oh nothing, I mean I saw you to go outside.
Did anything happen?

Speaker 4 (12:46):
Oh oh my god. No, no, we just like we
made out a little bit, but nothing happened enough more.

Speaker 5 (12:55):
Oh god, I mean he was cute.

Speaker 4 (12:58):
Yeah, it's whatever, though.

Speaker 5 (13:00):
I just feel like, you know, I always see you
hanging out with guys, and you're the pretty one, you're
the popular one, and I want to have fun and
meet someone too. I guess I just yeah, you.

Speaker 4 (13:13):
Totally should, like you deserve whoever you want in this world.

Speaker 5 (13:19):
Well, thank you for that. Like I said, you're such
a good friend, and I kind of am hanging out
with someone.

Speaker 4 (13:28):
Wait stop, no way, you're seeing someone else.

Speaker 5 (13:32):
Well I'm not exactly seeing someone, I mean not yet.
It's it's kind of complicated.

Speaker 4 (13:40):
What do you mean complicated? Like have you looked up
with him?

Speaker 5 (13:43):
But no, definitely not. I've only seen him to excess it.

Speaker 4 (13:48):
Oh oh my god, no, I.

Speaker 5 (13:51):
Mean yeah, just once. It's life.

Speaker 4 (13:54):
Actually, Ben used to always I seek to send him
pick like even of that working stuff. That's a freaking.

Speaker 5 (14:02):
Perb well Aaronessa thing it is been Wait what is Ben?

Speaker 4 (14:11):
What do you mean, so the.

Speaker 5 (14:13):
Guy that I'm kind of talking to it's your ex.

Speaker 4 (14:18):
Then wait, I'm just no, you called me from your
work song to tell me that you are talking to
someone who is my ex boyfriend.

Speaker 5 (14:32):
I mean, I respect you, That's why I call you
could kind of tell you that we were catching feelings
from one another, and.

Speaker 4 (14:40):
But how how can you then? You know he literally
cheated on me?

Speaker 5 (14:46):
Right, come on, girl, that's a theory like then and
I talk about it and he doesn't say that.

Speaker 4 (14:53):
Okay, No, please, please please tell me that you're not
defending my ex boyfriend. Now.

Speaker 5 (15:01):
I get that you guys had history, and I would
never do anything unless I got your permission. I'm asking
you if you'd be okay with it, and that's where
I'm going to leave it.

Speaker 1 (15:13):
Mmm.

Speaker 4 (15:15):
No, no, wow, that TV considering.

Speaker 5 (15:20):
That I gave you a break after you kissed my brother.

Speaker 4 (15:23):
Oh no, he was in the hospital. That doesn't count
at all.

Speaker 2 (15:33):
I didn't know the hospital doesn't count. It's fun to
have an emergency right now?

Speaker 4 (15:41):
Who are these people? Why are they on the phone?

Speaker 2 (15:43):
Hey, you're on the radio right now with a show
called Brooke and Jeffrey in the morning.

Speaker 4 (15:49):
Why why am I on the radio.

Speaker 2 (15:52):
This is very, very tea worthy. There's a lot of
drama going on between you and your friend Monica to help,
drama that we didn't even know about, honestly.

Speaker 1 (16:03):
Honestly, and I'm shocked that you didn't give her your blessing.

Speaker 4 (16:07):
You're what are you?

Speaker 5 (16:08):
Guys?

Speaker 3 (16:10):
I mean, I mean I wouldn't either.

Speaker 5 (16:12):
I wouldn't give anything.

Speaker 1 (16:15):
He's a gross dude, like you don't care about.

Speaker 2 (16:19):
He said, that's a theory. He doesn't believe that he
did remember that.

Speaker 4 (16:24):
You know what, whatever, If Monica wants to date Ben
and be cheated on and have a miserable life, then
go ahead. I don't even try anyone looking.

Speaker 3 (16:35):
That's the best she's gonna get.

Speaker 2 (16:36):
Yeah, it's a half blessing. So it's like a sarcastic one. Look,
the whole reason that Monica reached out to a radio
show for this is because she understands that it breaks
some rules of friendship and she's going to be crossing
some boundaries. She didn't want to do that without like
going through it the right way and asking your permission.

Speaker 5 (16:54):
I think you need a pick.

Speaker 4 (16:56):
I think you just need to pick me or him.

Speaker 3 (16:58):
No, don't do that. Aaron, did you hear her like, listen,
you have every guy is willing to make out with you.
It sounds like, which is great. Good on you, Aaron.
Monica needs somebody.

Speaker 1 (17:11):
And maybe maybe just because this guy cheated on you,
that doesn't mean that he's going to have a bad
relationship with Monica.

Speaker 2 (17:19):
Probably it's funny that Brook's so on board now with this.

Speaker 3 (17:25):
To date the ex, Monica is doing the right thing.

Speaker 5 (17:27):
This is the last time that I'm going to act
like our friendship is more important than any of that.
But I'm asking you one last time.

Speaker 2 (17:35):
Think about you kissing her brother in that hospital back to.

Speaker 3 (17:39):
The hospital part. I have a lot of questions about well,
I don't know that we have time.

Speaker 2 (17:42):
I don't think we have time to Aaron, what do
you say? Are you willing to give your blessing to Monica?
To date your ex is just a lot right now?

Speaker 4 (17:52):
I will think about it.

Speaker 2 (17:55):
The answer could be it's fair, it's fair, But the
at least she's willing to mull it over and come
back with a decision like that's better than.

Speaker 1 (18:02):
We could have accept I think it's going to be
texting the other friends in a group message.

Speaker 2 (18:05):
Without girls who will not believe what Monica asked me.

Speaker 5 (18:13):
Oh my god, Aaron, please don't do that.

Speaker 4 (18:17):
I'll get back to you.

Speaker 1 (18:18):
I just okay, Just remember you don't want this guy, right,
So who cares?

Speaker 2 (18:28):
Really, really good effort.

Speaker 5 (18:32):
Brooke and Jeffrey in the morning.

Speaker 2 (18:35):
We need to try to get an update from these
two and find out if Aaron ever gives Monica her blessing. Yeah,
because our producer has reached out to try and figure
out if there's been any update. No response yet, so
could still be mulling things over or Monica may have
already run off to Thailand with the X.

Speaker 4 (18:52):
See.

Speaker 1 (18:53):
I think you contacted the wrong person. We need to
do have contacted Ben. Oh, we don't have his obviously,
the reliable ex who said he didn't cheat.

Speaker 3 (19:01):
Yes, I trust that that guy.

Speaker 2 (19:03):
Says, because Aaron has every right to say no. I
don't feel comfortable with you doing that. It's too weird
for me. But if she says yes and this relationship
actually works out, just think of the material she'll have
for the made of Honor speech.

Speaker 6 (19:15):
Yeah, let me show you how they met and that
she plays our audio.

Speaker 2 (19:19):
Oh, there's so much potential. But we'll try and keep
you updated on what happens there. But if you ever
need help with anything going on in your life, any
awkward situation, reach out to us. We'll give you a
little bit of advice. Yeah, not necessarily great advice, but if.

Speaker 3 (19:34):
You listen to the show long enough, you'll know that
it's not good.

Speaker 2 (19:37):
We go check out all of our Awkward Tuesdays and
all of our content. They're up wherever you get your
podcasts at Brooke and Jeffrey
Advertise With Us

Hosts And Creators

Brooke Fox

Brooke Fox

Jeffrey "Young Jeffrey" Dubow

Jeffrey "Young Jeffrey" Dubow

Jose Bolanos

Jose Bolanos

Alexis Fuller

Alexis Fuller

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