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Jeffrey
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Jeffrey
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Jeffrey
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Jeffrey
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Brooke
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Olympics where doping is not only legal but encouraged. It's the Enhanced Games. Some call it grotesque, others say it's unleashing human potential. Either way, the podcast Superhuman documented it all, embedded in the games and with the athletes for a full year.
Mike
Within probably 10 days I'd put on 10 pounds.
Jeffrey
I was having trouble stopping the muscle growth.
Ad Host
Listen to Superhuman on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
Sofia
My mother in law spent years sabotaging our relationship until karma made her pay for it.
Jeffrey
All right Sofia, tell me about how we started this story.
Sofia
She moved in for two weeks, lasted five days, left a mess and then pressed her ear against their bedroom door and burst in screaming. When kicked out to a hotel, she called her son in law's workplace pretending his partner had been rushed to the hospital by ambulance.
Jeffrey
She faked a medical emergency and spoiler,
Sofia
that was just the beginning. To find out how it ends, listen to the okay Storytime podcast on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
Brooke
You've got texting problems and we've got solutions.
Alexis
Yeah, seriously.
Brooke
Brand new episode today on the second Date podcast. You found it. The official one. All right you, it's Brooke and Jeffrey in the morning and today we got a brand new textual Healing, where someone has a texting problem and we help them out. So you're gonna hear that in just a second. But we always love to start by highlighting our listeners. Yes.
Alexis
And Tintin Tin Joy said, I use your podcast as my daily shower timer. The second I skip the ads, it's go time. I need to be out before it ends or I'm late for work. Y' all are responsible for my hygiene and my paycheck at this point. Please read this during second date update so I can hear it mid shampoo.
Mike
Yay.
Brooke
There you go. Oh, you missed a spot.
Sofia
Ye.
Alexis
By the way, that reminds us, for the editors, we can never do like a 30 to 40 minute second date or this person will be very late.
Brooke
Yeah, she'll be in the shower for a long time.
Alexis
Yeah.
Brooke
All right, well, enjoy your shower and enjoy this brand new episode starts right now.
Jeffrey
There are certain things in life that require a huge leap of faith. Whether you're moving across country for a new job, proposing to a woman you just met earlier that day. Whoa.
Alexis
Wow.
Jeffrey
Or ordering delivery from a two star rated food truck in a strip mall. Because with big risk comes big rewards.
Brooke
That's right.
Alexis
Awesome food. Probably not, but it could be. Could be.
Jeffrey
That's why one of our listeners needs help today. He wants to take a huge leap of faith with a very special person in his life. And if he doesn't do it right, their six year friendship could possibly be ruined forever. Big risk, big reward. We're going to try to help him out in a brand new textual healing feeling next. Textual healing? Textual. Is it different texting your mom versus texting your love interest? For some of us, we could take the same cues, be polite, also playful, and put funny over flirty.
Brooke
No, no, no, no.
Jeffrey
Be more flirty first with your mom.
Brooke
None of it.
Jeffrey
Oh, well, I agree. Nobody wants to be like, bro, can you hurry up? And you're like, hold on, I'm flirting with my mom. Okay, Peach emoji. See?
Brooke
But it sounds just as bad if you say, hold on, I'm being funny with my mom.
Jeffrey
Yeah, the differences can be very subtle, a little tough to navigate. And that's where we can step in and help with a little textual healing, the segment where we help a listener craft the perfect message to send to whoever they need for whatever unusual situation they find themselves.
Brooke
We're hanging up. If they say they need help with their mom.
Jeffrey
Today, one of our listeners has reached out seeking some tender textual gratification with one of his love interests. Definitely not his mom.
Brooke
Sweet.
Jeffrey
At Least I hope not. His name is Mike. Mike, welcome to the show.
Mike
Hey, thanks, guys.
Brooke
Yeah, sorry about that. Weird start.
Alexis
Yeah, that was.
Brooke
We're going to get back on track for you.
Jeffrey
We do have a mom on this show that could help give you advice if that makes you feel more comfortable.
Brooke
Comfortable.
Mike
That'd be good. Yeah, a mom would be good.
Jeffrey
Nice. See, Brooke, did you hear that? He's into moms. He's pro mom.
Brooke
Keep going, Jeff.
Jeffrey
Keep going. On the mom stuff or into the love interest?
Brooke
Into the love. Interesting.
Jeffrey
Yeah, let's talk about that. Who do you want help texting?
Mike
I want him texting my friend Chloe.
Brooke
Oh, you say friends. Oh, you guys, is this one of those things where you're ready to make the jump from friendship to something more? With Chloe,
Mike
I mean. I don't know. I don't know. I don't know.
Brooke
I love that nervous energy.
Jeffrey
How long have you and Chloe been quote unquote friends?
Mike
Like six or seven years.
Brooke
And how long have you wanted more with Chloe?
Mike
I don't know. We've always been friendly, but like, I think from the beginning is the full
Jeffrey
six or seven years.
Mike
Okay.
Ad Host
Yeah.
Alexis
I feel like you got to tell us a little more than I don't know because we can't just text her that eight times.
Jeffrey
Yeah. Like, what's the nature of the friendship? Been like.
Mike
Yeah, yeah. I mean, we've just always been pals and she's always been in relationships and. Okay.
Brooke
And your window has opened.
Mike
Yes, it has. I just feel like she always has these, like, really handsome boyfriends. And like. Like a few months ago we were at a another friend's birthday and she basically just like talked to me in. In the corner like the whole time. And this has happened before. Like we always kind of wind up together in the corner of a room and I just feel like there's something
Jeffrey
there where she's not spending time with her boyfriend, she specifically hanging out with, using it to hang out with you instead.
Mike
Yeah.
Jeffrey
Yeah. Well, that's a good sign.
Brooke
See, all I'm hearing is she has handsome ex boyfriends and that's what matters.
Mike
Yeah, she's an awesome girl and she's the one who breaks up with them because she's great.
Brooke
Oh, that's cute.
Alexis
She's single now though.
Jeffrey
Yeah. What happened? How did this come out so that like, now is the right time to make your move?
Mike
It just is the first time I think since I've ever known her that she's like 100% single. There's no situationship. There's no. There's no other person. And I'm just wondering if it's the right time to be vulnerable and see if she'd be open to something. I just have no clue how to do that. Yeah.
Brooke
Have you ever gotten any vibes or
Alexis
any friends have said anything?
Brooke
Yeah, that Chloe may feel the same about you.
Mike
No one said anything, but it's just the thing I told you about the party. Like that I have 10 more examples of that where it's just. There's no need for her to like, be with me. Like, she could be with her literal boyfriend and it seems like she'd rather be with me.
Brooke
Yeah, that's cute.
Mike
You know, I'm just a guy, but like, I feel this attraction towards her and I like, this can't be one sided. This can't be just me.
Alexis
Yeah. Okay, you gotta get a feeler out there to see if she likes you.
Jeffrey
Right. So. But I'm just wondering, where in this puzzle piece does your mom come in?
Brooke
Mom out.
Jeffrey
There's no mother involvement whatsoever.
Mike
No, no, no mom involved.
Jeffrey
Okay, well, that takes my area of expertise out of this. It's gonna be more on Brooke now to come up with something good to send your love interest.
Brooke
I was going to say, where have you left your last text with her? Because I assume you guys are friends, so you text. I mean, are you at a friendship level where you text individually or is it always group chats?
Mike
No, no. Like, we'll send each other funny videos and stuff or like little things.
Jeffrey
Yeah, but how do you move the relationship now from a friendship into a potential romance? That's what you're wondering to do via a text message. So let's start brainstorming.
Alexis
Let's just break the ice with. So you're single, huh? Okay, maybe not.
Mike
Ye.
Jeffrey
Alexis.
Ad Host
What?
Jeffrey
Do you have any ideas of what he should send? Okay, moving on.
Brooke
That was good. Thank you. Inside joke?
Alexis
Oh, that's vague, but that's all I got.
Okay, send each other memes and videos. You may have an inside joke of something.
Mike
I mean, they're so like circumstantial, you know, they like fade in. Yeah. No, no.
Jeffrey
Okay.
Alexis
Okay. We almost had something.
Brooke
I mean, maybe you bring up the fact that she's single and it's like self deprecating, like, oh, you dropped another model boyfriend again, huh? I hope he's not. He's not too heartbroken or, you know, like something sarcastic, you know what I mean?
Jeffrey
Hey, lonely party of you.
Brooke
No.
Alexis
Wow.
Jeffrey
What are you doing?
Brooke
She's doing the breaking up. She's not heartbroken about it, so it's
Alexis
like a backhanded compliment. Yeah, you could actually leave that into more like, good thing you and me could never get together. I'm way too attractive for you or something like that.
Jeffrey
Okay. But silly playful, like you would with your mom. Yes.
Brooke
I think. I think if we start by bringing up the fact that she's single right now, then it'll help us lead to the mental. Yeah.
Jeffrey
Okay. Go ahead.
Alexis
Towards that.
Jeffrey
Start typing. Remind her that she's single.
Brooke
No.
Jeffrey
Go for it, Mike.
Alexis
Woke up without a boyfriend.
Brooke
Yeah. Wow. Heard you dropped another from, I don't know, America's Top Model.
Jeffrey
What do you think about that, Mike?
Mike
I mean, yeah, that could work.
Jeffrey
I would start typing.
Mike
Okay.
Jeffrey
Hey, like, heard you had to drop another beautiful model boyfriend.
Brooke
Another heartbroken, gorgeous man out on the streets.
Jeffrey
Laugh emoji.
Alexis
I'd ask if you're okay, but I know you're fine.
Brooke
Yeah, that's good. You know, I'd ask if you're okay, but I know you're fine.
Alexis
Yeah, like, you're also being a good friend.
Mike
Heard you had to drop another beautiful model boyfriend. What was the next thing I'd ask
Brooke
if you're okay, but I know you're probably fine.
Alexis
Yeah. And then an emoji.
Jeffrey
Laugh emoji.
Alexis
Laugh emoji.
Mike
Yeah. I'd ask if you were okay, but I know you're probably fine. Laugh emoji. Okay, got it.
Alexis
Nice.
Mike
All right.
Brooke
And then she can write back something sarcastic about how the hot ones are not always the smart ones or something.
Jeffrey
Yeah, or it causes a rift in your friendship because you accused her of being single. So we'll see how it goes.
Brooke
She dumped him. Jeff, not all breakups are bad. Yeah, I don't know if you know
Jeffrey
that when they're beautiful model boyfriends. I would think it hurts a little
Brooke
bit more, but she's going through them, dude.
Jeffrey
Yeah. So we've sent that. We'll see if your friend Chloe responds when we come back and we do more Textual healing Non mom edition coming up.
Alexis
Why do you.
Jeffrey
It's not moms we're doing right after this.
Mike
Hold on.
Jeffrey
We're in the middle of textual healing with our overly talkative listener Mike, who would just not shut up about his longtime friend Chloe, who he's hoping to become more than just friends with now that she's finally single and moved on from her hunky, well endowed model boyfriend.
Brooke
We didn't know that part.
Jeffrey
Well, we can assume. I don't know so how do we get the friend ball rolling in the romantic direction? We suggested he start by first reminding her that she's single in a playful way by saying, wow. Heard you had to drop another gorgeous model boyfriend. I'd ask if you're okay, but I know you're fine. Laugh emoji.
Ad Host
Yes.
Alexis
Yeah, yeah.
Jeffrey
So we sent that a little while ago. Has she responded yet, Mike?
Mike
Yeah, she actually did.
Brooke
Oh. I can never tell if you're excited, Mike, like, what your emotions are.
Alexis
You must be just so nervous right now.
Jeffrey
Or whatever medications you're on, they're totally working.
Alexis
There you go.
Jeffrey
But she wrote back. What did she say?
Mike
She said, yup. Guess I need to go to the GQ store at the mall and find another.
Jeffrey
Another model boyfriend.
Alexis
Sense of humor. That's funny.
Brooke
That's pret funny. What if you wrote back and said, but have you ever tried the Boot Barn? Oh, yeah. And that's where we go on to say that I'm the guy at the Boot Barn.
Alexis
Does it.
Jeffrey
Do we have to go all the way to the basement from the models all the way down to, like, backwater?
Alexis
You ever been thrift shopping?
Jeffrey
What about the middle? The Gap?
Alexis
The Rack Gap?
Jeffrey
Yeah.
Brooke
Okay,
Jeffrey
Mike, hopefully you're not getting offended by any of this.
Mike
No, no, no. All right, so, like, we're going with Boot Barn or the Rack.
Alexis
Wait, don't, like, take us literally. We're kind of kidding you.
Brooke
I wasn't.
Jeffrey
I'm actually supporting Brooke's idea a little bit here because the humor's there. It's still a little flirty, playful.
Alexis
Okay.
Jeffrey
And the insinuation is. Look at me.
Brooke
This is what I think you should say. But have you ever tried shopping at the Boot Barn? I'm still with boot Barn. I think it's funnier, but emoji. Yeah, but whatever. The Rack.
Jeffrey
Whatever low class store you want to, like, refer to as. Yeah, put that in.
Alexis
She still kind of likes, though.
Yeah, yeah, like, make it a good one.
Mike
Yeah, I do like boob barn. So I am going to say Boobart.
Alexis
Oh, he likes Boobart.
Jeffrey
The question is, do you think that she'll 100% understand the subtle messaging that he's trying to put out there?
Alexis
Yeah, I friends and they have humor.
Brooke
She's dropping hot boys because she's emotionally intelligent. Okay, she gets it. She's the one that brought up the GQ store.
Alexis
Okay, Funny.
Jeffrey
All right, cowboy, send that Boot Barn text and see what she says.
Mike
All right. Someone say, maybe you should try shopping at the Boot Barn. And then boot emoji.
Jeffrey
Oh, I like that.
Brooke
Yeah.
Mike
All right, Send.
Alexis
And she's gonna be like, great idea. I love cowboys.
Brooke
Yeah.
Alexis
Darn it. Didn't think of that.
Jeffrey
Or she's just gonna go, like, get a wardrobe thing. Like, takes it too literally.
Brooke
So, I mean, we may need to then follow up immediately with saying that you're the option. Yeah, right.
Jeffrey
Like, I am the boot in question.
Brooke
Yes.
Alexis
Yeah.
Are we just gonna name stories back and forth with her?
Brooke
Because the joke will go on. Like, now we've been playful. I think next we need to be direct.
Alexis
Yeah. And hopefully she just gets it, and it's like, oh, really?
Brooke
Or just say, actually, I would love to take you out on a date.
Mike
I mean, honestly, guys. Hold on, hold on. She responded. She responded.
Jeffrey
Oh, okay. What'd she say?
Mike
I'm actually starting to realize the pretty ones aren't as pretty on the inside. Yeah, see, they're actually pretty boring. Eye roll. Yeah, more like a temporary cat toy. Play with them for a while till it gets old. Yeah, okay.
Brooke
Oh, I like her.
Jeffrey
She's getting sick of the pretty boys, so she's looking for this.
Alexis
This is still just two friends talking, though. I mean, how do we get it to be a little more flirty?
Brooke
Yeah, I mean, I think this is part of the more direct line. Right. Because she's getting more serious right now in this. In this text exchange. We can drop the humor now.
Alexis
Maybe just ask. You said drop the humor. Maybe it's like, have you ever considered dating a friend? Yeah, literally. That's a general question.
Brooke
I love it.
Jeffrey
Mike, what do you think?
Mike
I'm scared, but, yeah, let's do it.
Jeffrey
I mean, Mike, I could tell by your emotions that you're super scared. You're all over the place. You got to calm down a little bit. Refocus. Okay.
Alexis
Squirrelly over there.
Brooke
Was that his big energy? Is that what you were?
Jeffrey
It was kind of overwhelming, Mike. So let's temper that and write this message. What should he say?
Alexis
Jose, just tell her. Have you ever considered dating a friend?
Jeffrey
And what about the guy shrugging emoji?
Alexis
Yeah, that's playful.
I don't think it matters.
Brooke
Yeah, okay.
Jeffrey
Buff guy shrugging. There we go.
Brooke
Now.
Alexis
Now I feel like it's false advertisement
Brooke
for what he said that he's offering.
Alexis
Do both arms.
Mike
Have you ever considered dating a friend?
Jeffrey
Shrug emoji.
Mike
Shrug emoji.
Brooke
Send it.
Alexis
She's got it. Talking about you.
Well, I hope you don't have other hot friends in your group, because.
Jeffrey
Oh, shoot. I was thinking About? Oh, I wish you hadn't sent it, because I was thinking of adding something about a mom. Like, something really funny about it. Oh, it's too late.
Alexis
Ever dated a friend? A mom? A mom who's a friend?
Brooke
You get on one thing, and we just can't let it go, can we, Jeff?
Alexis
It's like he's holding in his back pocket.
Brooke
Yeah, come through.
Jeffrey
Okay. Boot lady. Jeez.
Ad Host
Fine.
Brooke
Dude, that was clutch. I did, right?
Alexis
It got us to here.
Mike
Oh, my God. Guys, she texted back, oh, my God.
Alexis
Oh, my God good or oh, my God bad?
Jeffrey
What did she say?
Mike
Okay, she said, oh, so you want me to date down? Wink face.
Brooke
She knows it's you down.
Jeffrey
No.
Alexis
Or she doesn't know it's him.
Jeffrey
Why would she say the wink face?
Alexis
Maybe joked about boot bar.
So she's cheating.
Brooke
She's flirting back. You don't send a wink emoji without being flirting.
Jeffrey
So you want me to date down?
Alexis
Wings.
Mike
There's more.
Brooke
There's more.
Mike
There's more. She said I'd be lying if I said it hadn't crossed my mind.
Brooke
Oh, my gosh.
Alexis
Wait, I do we need clarification. I'm too excited. Like, but you're talking about me, right?
Brooke
So this is what you write back. You got to check right back. Does this mean I can take you to dinner and the discount Ben this weekend?
Alexis
Oh, that's good. You're bringing. It's called a callback.
Jeffrey
You know, Brooke, Alexis has no idea what you're saying.
Sofia
How about clearance rack? Would that work for you?
Alexis
If you want to throw in a coupon joke.
Jeffrey
She's giving you the green light to go for it. It sounds like so just go for it. You don't have to be cute about it.
Alexis
We do need to confirm, though, it
Jeffrey
has to be you.
Brooke
Does this mean I can take you to dinner, though, this weekend?
Mike
There you go.
Jeffrey
All right, Mike, please calm down. You are all over the place right now.
Mike
All right, all right. Does this mean I can take you to dinner this weekend?
Alexis
Oh, I'm scared. This is too bold.
This could be super smooth for a train wreck.
Brooke
Yeah, I'm excited.
Jeffrey
Your voice did crack when you say it. Are you sure you want to go through with this?
Alexis
It's not going to cry.
Brooke
Do it. She opened the door.
Mike
I sent it. I sent it, I sent it.
Jeffrey
Well, no turning back now.
Brooke
I'm so excited.
Jeffrey
This is either going to make a whole new wonderful relationship or ruin the friendship forever.
Brooke
She sent a wink emoji. It has to be him.
Alexis
You're Right. Yeah, the wink emoji.
Jeffrey
I send my mom wink emojis all the time. It doesn't mean anything.
Brooke
We're back here.
Jeffrey
Okay, Mike, I'm gonna give you some instructions first. Lay on the ground.
Alexis
Oh.
Brooke
What?
Jeffrey
Close your eyes.
Brooke
What?
Mike
What?
Alexis
Yeah, don't do it.
Jeffrey
We're just killing time until we get a message back. Close your eyes. Unzip.
Brooke
What?
Jeffrey
We don't know. I'm just trying to fill the empty space.
Mike
Okay. Oh. Oh, my.
Jeffrey
Okay, he unzipped.
Alexis
Wait, why'd you say oh, no?
Brooke
He got the response jack.
Mike
Detect it back. Detect it back. Detect it back.
Brooke
What'd she say?
Jeffrey
What did she say?
Mike
She said if you can keep your emotions in check, you can come over and spend the night.
Alexis
Whoa.
Wait a minute.
Hey.
Jeffrey
What?
Mike
That's engaged.
Alexis
This is good, right?
Brooke
She's obviously being sarcastic about his emotions because we've seen how emotional this guy is.
Jeffrey
Yeah, definitely. I mean, Mike, you're not spending the night. You want a long term relationship. Relationship. You don't want to be a cat toy.
Brooke
Dude, they've been friends for six or seven years. You could spend the night.
Alexis
Yeah, you go right over there right now.
Mike
I want. I 100 want to be a cat toy.
Brooke
That's right.
Alexis
They've had plenty of dinners together.
Jeffrey
Okay, well, I think so.
Brooke
Cute.
Jeffrey
Our job is done.
Brooke
You have a slumber party.
Mike
Thank you, guys.
Alexis
You're welcome.
Wait.
Brooke
Reply yes or something.
Jeffrey
How are you feeling right now, Mike?
Mike
Mike? Three boots, three boot barns.
Brooke
Yes.
Mike
Really good.
Alexis
Don't text that back.
Jeffrey
You've ruined him.
Brooke
I would write back. Just warning you, I'm not bringing my own sleeping bag.
Alexis
What?
Jeffrey
What? Okay, you've lost Alexis again.
Ad Host
Brooke and Jeffrey in the morning.
Imagine an Olympics where doping is not only legal, but encouraged. It's the enhanced games. Some call it grotesque, Others say it's unleashing human potential. Either way, the podcast Superhuman documented it all, embedded in the games and with the athletes for a full year.
Mike
Within probably 10 days.
Jeffrey
I put on 10 pounds. I was having trouble stopping the muscle growth.
Ad Host
Listen to Superhuman on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
A win is a win. A win is a win. I don't care what y' all say. Yep, that's me. Clifford Taylor iv. You might have seen the skits, the reactions, my journey from basketball to college football or my career in sports media. Well, somewhere along the way, this platform became bigger than I ever imagined. And now I'm bringing all of that excitement to my brand new Podcast the Clifford Show. This is a place for raw, unfiltered conversations with some of your favorite athletes, creators, and voices that not only deserve to be heard, but celebrated. One week I'll take you behind the scenes of the biggest moments in sports and entertainment, and the next we'll talk about life, mental health, purpose, and even music. The Clifford show isn't just a podcast. It's a space for honest conversations, stories that don't always get told, and for people who are chasing something bigger. So if you've ever supported me or you're just chasing down a dream, this is right where you need to be. Listen to the Clifford show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. And for more behind the scenes, follow at Clifford and at Tick Tock Podcast network on Tick Tock.
Jeffrey
You know, it's been about a week since we recorded that and we still have not heard how it went when he went to her place.
Alexis
Is that a good thing or a bad thing?
Jeffrey
I don't know. Either it went amazing and he's never left, or it went horrible and he doesn't want to talk to us. Oh yeah, we gotta get an update date from him at some point.
Brooke
But I will say they were so cute.
Jeffrey
They were cute. I have visited the Boot Barn, though, since the call. That place is cute.
Brooke
I'm gonna tell you, I have some other shopping hot tips for you too, if you need.
Jeffrey
What other store do we have to visit that's discount low budge.
Brooke
This one doesn't actually have a brand name attached to it, but it is in a back alley and there's a guy who sells an incredible deal.
Alexis
Jeff, you really asked Brooke this right now?
Yeah.
Jeffrey
I'm sold. Blindfold me and lead me into that back alley. Sometimes nothing bad will happen.
Brooke
That's.
Jeffrey
And nothing bad will happen. If you email our show for help. We can help you with your textual healings. Your second date updates, your awkward Tuesdays sometimes end good. Sometimes that's pretty good for us. Find us online wherever you get your podcast. It's Brooke and Jeffrey in the morning.
Episode Title: Textual Healing: America's Next Top BF
Date: April 30, 2026
Host: iHeartPodcasts
Main Hosts: Brooke, Jeffrey, Alexis
Listener: Mike
This episode features a brand new segment of "Textual Healing" on the Second Date Update podcast. Listener Mike seeks help from the hosts to navigate a high-stakes text conversation—he wants to move from a six-year friendship with his friend, Chloe, to something romantic now that she is single for the first time since they've known each other. The hosts step in to help Mike craft the perfect texts to make his intentions clear without risking their friendship, blending humor and vulnerability.
“I just feel like she always has these really handsome boyfriends, and like...we always kinda wind up together in the corner of a room...there's something there.” – Mike (06:33)
The hosts brainstorm how to start the conversation in a lighthearted, non-threatening way.
Brooke and the team land on a smart, slightly self-deprecating approach referencing Chloe’s dating history with “model” boyfriends.
Final Text:
"Heard you had to drop another beautiful model boyfriend. I'd ask if you're okay, but I know you're probably fine. 😂" (10:51)
Chloe responds positively with a witty retort referencing "shopping at the GQ store" for another boyfriend (12:51).
"Yup. Guess I need to go to the GQ store at the mall and find another." – Chloe (12:58, via Mike)
“I love it.” – Brooke on the direct question strategy (15:58)
"I 100 want to be a cat toy." – Mike (20:08)
| Timestamp | Segment/Topic | Highlights | |-----------|----------------|------------| | 03:15 | Episode Theme Launch | Jeffrey intro about risks for big rewards—setting up Mike’s situation | | 05:11 | Listener Joins | Mike introduced – “pro mom” jokes begin, Mike clarifies he wants to text Chloe | | 06:33 | Friendship Background | Mike shares history and highlights their repeated, intimate party interactions | | 10:51 | First Playful Text | Hosts help Mike send first banter-filled message referencing Chloe's exes | | 12:58 | Chloe’s Response | Chloe responds with humor, referencing the "GQ store" | | 14:28 | “Boot Barn” Text | Further playful banter, Mike suggests Chloe “shop” at Boot Barn (himself) | | 15:16 | Chloe’s Sincere Text | Chloe admits pretty guys are boring, hints at wanting something different | | 16:37 | The Direct Ask | Hosts prompt Mike to ask “Have you ever considered dating a friend?" | | 17:47 | Chloe’s Flirty Response | Chloe says it’s crossed her mind, jokes about “dating down” | | 18:31 | The Dinner Invite | Mike asks Chloe to dinner; they await her reply | | 19:41 | Chloe’s Invitation | Chloe invites Mike to spend the night—very positive, flirty outcome | | 20:22 | Mike Expresses Excitement | Hosts (and Mike) celebrate the win, wrap up the episode’s main segment |
In this Textual Healing segment, Mike’s leap from friendship to potential romance with Chloe is a success—thanks to well-crafted texts and some moral support (and jokes) from the Brooke and Jeffrey team. The episode is a masterclass in using banter to break the ice and the power of being direct when the time is right.
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