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Brooke
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Ryan Seacrest
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Alexis
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Brooke
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Jeffrey
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Carson
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Carson
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Brooke
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Carson
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Jeffrey
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Brooke
Hey, it's Brooke and Jeffrey in the morning and we've got a brand new second date today. And yes, it's really proof why you need to keep your car clean. Yeah, you know, this guy's date pulled something out from between the seats of his car that ruined literally their entire night.
Jeffrey
Oh, no.
Brooke
Yeah, I know, I know. It's. You're gonna hear it in just a second. We're gonna start. Of course. Always with your comments though. What do you see? Ale. Yeah. Bibs said your show is the reason I'm late for work every day. With a heart emoji. Tell your bosses.
Leanne
Hi.
Brooke
Yeah, you're gonna get fired.
Jeffrey
But you'll laugh.
Brooke
Hey, not unless you get the boss to listen too. Yeah, like, sorry I'm late, but let me tell you what just happened. You know, you gotta do it. Exactly. Exactly. There it is. And here is your brand new second date update.
Carson
Second date update. For a lot of guys on the dating apps, coming up with the perfect opener is like painting the Mona Lisa.
Brooke
Wow.
Jeffrey
Takes a lot of time, huh?
Brooke
Pure art.
Carson
You just put something down, stand back, you study it, add a little word here, adjust that line there, take off the eyebrows there. Yeah. Toss in an extra emoji. Delete that pun. And after four hours, you finally send her.
Jeffrey
Four hours.
Carson
Hey, what's up?
Brooke
Yeah.
Carson
Wow. No response.
Brooke
But you put hay in there, which I know, like, so personal.
Jeffrey
You shouldn't have used the apostrophe.
Carson
Is that what it was? I thought the three question marks were going to work, but today we have a listener who says he actually put in some work, real work, into figuring out an opening line with a 60% reply rate, which is extremely high for guys on these apps.
Brooke
Is it?
Carson
That's very, very high. Yeah. OK, what's the average? Like 2% reply rate? Maybe lower.
Brooke
How many messages are you guys sending?
Carson
It's very difficult. His name is Carson. So, Carson, welcome to the show, ma'.
Brooke
Am.
Leanne
How are you doing, guys?
Brooke
Oh, are you going to let him deliver the line?
Carson
Yeah, I don't know what the Line is.
Leanne
I'm curious.
Carson
I don't have it written. So, like, what kind of line are we working with here, Carson?
Leanne
Like, we don't even need to talk. But I was wondering if you would critique my profile. I'm new here.
Brooke
Oh, Alexis.
Jeffrey
Okay.
Carson
What do you think about that, Alexis? An invitation to critique his profile?
Brooke
I don't know.
Jeffrey
But they're tricking you into looking him up.
Brooke
Yeah. Aren't they? Then looking at your profile with a negative viewpoint, because you're only going to pick out negative stuff to be funny about. You're not going to say.
Carson
Okay.
Jeffrey
But it's a conversation.
Carson
So Alexis is in the 40 that would not reply to this.
Brooke
Probably reply something so rude that they don't reply back. Well, even, like, I'd be like, this photo's terrible.
Carson
Even that. I mean, that's a response in itself. That's a win, right, Carson? Even if it's mean.
Leanne
Yeah, I mean, it did lead to someone. Her name is Leanne.
Carson
Okay, Leanne. Okay.
Brooke
She said. Yeah.
Carson
What was her critique?
Leanne
She said I should smile more in photos because I look too serious.
Brooke
Oh, that's a nice one. Yeah.
Carson
Okay. Yeah, if you have a good smile, then you should be showing that off. And women would like that.
Jeffrey
And pro tip, girls will love it when you tell them that, too. You should smile more. You look so good when you smile. Right, ladies?
Carson
Just in the photos. Yeah.
Brooke
So did you send her a personal pic of you smiling?
Leanne
I did not. I said, well, you should see my smile in person.
Brooke
Oh, even better.
Leanne
She said, okay.
Brooke
Oh, she said okay.
Carson
And you're like, look to your left out your window right now.
Brooke
Here it is.
Carson
And you're smiling.
Brooke
So what did you guys do for your date then?
Leanne
I offered to pick her up. We ended up going to a steakhouse.
Jeffrey
That's awesome.
Brooke
Wanting to impress her with the steak dinner. I mean.
Jeffrey
Yeah.
Brooke
You must really like this woman.
Leanne
You know what? She's. She's great. You know, we went to the steakhouse. Things went really well. It was everything I hoped it would be.
Brooke
I want to hear some highlights.
Carson
Did you smile at her the whole time?
Leanne
I tried to smile more. Yes. Good.
Carson
Okay. So she sees that it could be.
Brooke
Creepy if it's too much.
Jeffrey
That's all he did.
Carson
Hey, how's your steak?
Brooke
With a steak knife in hand. What did you guys connect over?
Leanne
Well, she's a real. In the sports, I'm a big sports guy, so that was an instant connection. We like similar kinds of music.
Brooke
Okay.
Carson
I mean, this all sounds really good. There was Nothing awkward that happened on the date.
Leanne
Everything was great. The awkward moment was on the way home. She saw something between the seats of my car.
Brooke
Uh. Oh.
Leanne
And she reached down, she pulled it out, and it was a canister of lipstick.
Carson
No.
Leanne
Oh, I know, I know that looks really bad. It probably looked like I was on another date, but.
Jeffrey
Or you just tell her, like, look, that's not my shade. Yeah, a little bit.
Carson
I have mine at home.
Brooke
Yeah, I mean, anyone could have dropped it in your car. It fall out of a pocket?
Jeffrey
I don't know. Sister or friend or.
Brooke
What did she say?
Leanne
Well, she. She certainly wanted to know where it came from. And I was. I was. I was honest with her. You know, I borrowed my ex girlfriend's car.
Brooke
Wait, you were driving your ex girlfriend's car?
Jeffrey
No, it wasn't your car.
Brooke
Oh, no. That's worse than.
Bubba Wallace
Just.
Carson
Did that totally smooth everything over for the conversation.
Leanne
Tell her that, you know, mine was in the shop. I was trying to be straight up with her. Obviously the vibe kind of changed at that point.
Brooke
Why didn't you just say a friend?
Leanne
If I could go back and change it, I think I would.
Jeffrey
That is it.
Leanne
Yeah, it looked like I. Look, I thought I was getting a good night kiss. Everything was great. Obviously that didn't happen. Yeah, that's. That's why I'm here. I'm hoping maybe you guys can help me.
Jeffrey
Wait, and now she's not calling you back? Like you haven't smoothed it over yet?
Leanne
No, I haven't heard from her since. This has been about a week or so.
Jeffrey
So everything was going good circumstance.
Brooke
What's the relationship with you and your ex? Before we call her, they're on good.
Carson
Terms enough for her to let him borrow the car.
Brooke
Yeah. How good of terms?
Leanne
Like, we were always friends. We tried to date. It didn't work out. We're still friends.
Jeffrey
That's so cool you guys can do that.
Brooke
Okay, that sounds different when you try to date somebody. Yeah, so, I mean, like, you could describe her as a friend instead of an ex. For sure.
Leanne
Yeah.
Brooke
Did you get a chance to explain that to Leanne?
Leanne
I didn't get a chance to because we were so close to her house. That was kind of the end of it.
Carson
Honestly, it's probably for the best. You don't probably want to be gloating about how great of a relationship you have with your ex girlfriend on a first date with somebody else.
Brooke
I'm sorry. If you're driving her car, you're going to want to explain playing something like it's better than we're still sleeping together.
Jeffrey
What answer is good? When you're like, she's the best, or you're like, oh, I hate her.
Carson
Yeah. You're driving her car.
Brooke
No, I think it's a green flag if someone can get along with their ex. For sure.
Carson
Absolutely.
Leanne
You know, well, that's why I'm hoping you guys can get her on the phone and help me explain that to her, because I don't know if she's gonna listen to me.
Brooke
Okay.
Carson
All right, I'm gonna let Brooke tackle that. I was gonna say the girls need.
Brooke
To handle this, cuz, like, I'm friends with all sorts of exes.
Carson
Yeah, yeah.
Jeffrey
Coming from you, it's good. It's easy for a guy.
Brooke
Oh, yeah?
Carson
Yeah. What's wrong with him hanging out with that?
Leanne
So, yeah.
Carson
Yeah, yeah. Anyway, we'll call Leanne for you after this and try and help you get your second date update in just a minute. Second date update. If you're just joining us, let's quickly recap Carson's first date with a little game of Good or bad steakhouse dinner.
Brooke
Good idea.
Carson
Good. Lots of smiling. Good. Picking her up in your ex girlfriend's white Jetta. I don't know.
Brooke
I had a white Jetta. That's good. Every blonde had a white Jetta.
Carson
Every ex girlfriend drives that.
Brooke
I had a blue Jetta.
Carson
So we're thinking that's probably the big red flag that's been scaring Leanne away from a second meetup with Carson. But Brooke wisely pointed out, actually, it could be seen as a green flag that he doesn't have a toxic relationship with past love interest. Right, Brooke?
Brooke
Dude, I think that if you can be friends with an ex, it doesn't mean that you still have feelings for them. It's when you still have feelings is when things get dicey and you can't talk to them and you're angry and everything.
Carson
Okay, but what about friends with benefits? No feelings.
Brooke
Well, I mean, it's an X, so it doesn't really count.
Carson
All right, Carson, does that feel good? Does it give you a little bit of hope before we make this call?
Leanne
I'm optimistic.
Brooke
Okay, but there's no benefits with your ex, right?
Leanne
No, no, no, no, no.
Brooke
Okay. Okay, good. Good.
Carson
Yeah.
Brooke
Well, besides the car, he does get to borrow her car, right? I meant the different types of.
Carson
Not the ph benefit. So let's reach out to Leanne. Hopefully she picks up and we can explain this whole thing and get her to go out with you again.
Leanne
Okay, sounds great, guys.
Brooke
Here we go.
Carson
Dialing you right now. Let's do it.
Leanne
Hello?
Carson
Hey, is this Leanne?
Bubba Wallace
Yeah, this is her. Who's this?
Carson
Well, this is actually a lot of us. Yeah, a whole ensemble of people called Brooke and Jeffrey in the Morning. We're a radio show.
Jeffrey
Hi, Good morning.
Bubba Wallace
Good. Good morning.
Jeffrey
Thanks for saying it back. People don't say it back a lot. I appreciate that.
Brooke
It's like when you say you're welcome or thank you. Yeah.
Jeffrey
You're a nice person.
Carson
Leanne, we're hoping that this can be a good morning for you because we're doing something called a second date update.
Bubba Wallace
Okay. All right. You know, I've seen it. I see it with social media.
Carson
Oh, you don't sound like you're a fan.
Brooke
Yeah. So. Well, thank for finding on social media. You can go to our podcast too.
Carson
She doesn't sound. She didn't sound like she liked it.
Brooke
Comes up in the algorithm. She doesn't look for us. Always be promoting. All right.
Bubba Wallace
It's always a disaster. It's always some nightmare case.
Brooke
Not. That's not true. No, that's not true.
Jeffrey
No, we only air the disaster.
Brooke
Just the ones that go viral.
Carson
Yeah.
Brooke
Yeah.
Carson
And we're hoping this is not one of those. That you'll never even see this in your feed because we're reaching out based on a date you went with with a guy named Carson.
Bubba Wallace
Oh, okay.
Brooke
Would you call it a disaster, your date with Carson?
Bubba Wallace
I don't know. Carson.
Leanne
What are you doing?
Bubba Wallace
Carson?
Carson
Yeah, so we spoke to Carson earlier, and he had really glowing reviews about the date. Just. What we know from it is that you two connected on a dating app. You said you really like to smile, had a nice dinner at a steakhouse. There was no kiss at the end. He was a little surprised by that, but.
Brooke
No, Disappointed, I think.
Carson
Disappointed. But now you're not open to another one. So he's trying to figure out if there's a reason.
Bubba Wallace
He must have left something out.
Carson
I left something out.
Brooke
I think you did. Yeah. You did, actually.
Bubba Wallace
I mean, I would be embarrassed, but he was driving his ex girlfriend's car.
Carson
Okay. Yeah, yeah, he did tell us that. I just didn't want to recap that part in case it wasn't a big issue for. So I was kind of hoping.
Brooke
What was your reaction when he told.
Bubba Wallace
You that that's not okay. Why that's not okay? Like, okay, that just means that someone special in your life is still in your life.
Jeffrey
I mean, technically, it sounds like you.
Carson
Feel threatened by the ex girlfriend a little bit.
Bubba Wallace
I know. Not that I've just. I've dated guys in similar situations and it always ends bad in my. My personal situation.
Carson
Okay, well, that's okay that you can think that, but let Brooke explain to you why you're wrong.
Brooke
That's not what I'm trying to do. But I do think that you could maybe change your stance on a little bit if you thought of it more as like a green flag. Like, here's a guy who still respects someone that he dated that he. That was. He was close to, and it's good that they can still have a non romantic relationship, right?
Bubba Wallace
Yeah, I guess. I never considered it that way.
Brooke
I mean, have you ever, like, had a friend and then got your feelings kind of mixed up in that friendship? Like, it's hard to have opposite gender friends because you're like, oh, my God, how much do I like this person? And then you try out dating and you're like, whoa, I didn't like him that much.
Carson
Did you know that was the case with Carson, that he was friends with that girl first before they tried dating, and then it didn't work out?
Brooke
Yeah, they realized that they weren't meant to be together.
Bubba Wallace
I mean. No, no. I mean, this is all kind of like a lot in general, but Good point.
Brooke
Okay.
Carson
Okay.
Brooke
Look at you being a reasonable human. I love it.
Carson
Okay, so. So is that something that would maybe change your mind a little bit about possibly seeing him and giving him another chance?
Bubba Wallace
Possibly. The radio person. I don't know her name, but like, she did bring up some pretty decent.
Brooke
Points, so I feel like I didn't deliver that well.
Jeffrey
Her name is Alexis. Give her all the credit.
Carson
I. I mean, this all sounds to us in the room here, but I bet it sounds even better to Carson, who's been quietly listening on the other line, hoping to talk to you.
Bubba Wallace
Carson has been listening this whole time.
Brooke
Are you kidding me? I can hear you smiling through the phone.
Carson
Yeah, I think he's there. Carson.
Leanne
Hey. Hey, guys. Yeah, I'm here.
Bubba Wallace
Carson, what are you doing? What are you doing all of this for?
Brooke
What is this look? They are so cute.
Leanne
I felt a connection with you that I haven't felt with anybody. And I really want to try to make this work.
Jeffrey
That's adorable.
Bubba Wallace
That's really sweet to hear that from you. Yeah, it is.
Brooke
See, he's not like those other guys that you dated that were yucky, you know, with their exes and things.
Jeffrey
Yeah, yeah, yeah.
Leanne
All right, well, look, I need to be 100% honest with you. We're getting it all out there right now.
Brooke
Okay?
Leanne
I do live with. I do live with my ex.
Carson
Wait, wait, wait, wait, wait, wait, wait, wait.
Leanne
That's how I was able to borrow the car.
Carson
Brooke, Brooke, how dare you support this and say that it was totally innocent and no red flags.
Brooke
Why do you live with her?
Carson
Yeah, Brooke, he's different, right?
Leanne
He's like a sister. It's really not a big deal.
Brooke
A sister that you slept with?
Carson
No, but they're in a good place now. Brooke, you said it yourself.
Brooke
You don't live with your ex. That's like. That feels like you were living together and then you broke up and you never moved out. Did you move in together when you were in a relationship?
Leanne
I mean, I don't know. I don't really remember. There was a lot going on. It just kind of happened. I mean, it's like a timeshare situation for us. We split the rent, we rotate the car. It's a good setup.
Bubba Wallace
I seriously, like I told you guys, this is all disastrous.
Leanne
Leanne, look it. Trust me when I say this, it's not a disaster.
Jeffrey
Oh, God, That's a big trouble.
Brooke
That's a. Famous last words.
Leanne
Why don't you come over this weekend? We can. We can hash it out and. It's my weekend to have the master bedroom.
Brooke
Wait, what? Oh, there's only one bedroom.
Carson
You guys swap the bed. That's a good living situation.
Leanne
Hey, it works for us. Don't judge.
Brooke
Where do you sleep when you don't have the bedroom?
Leanne
I mean, the car. That's what it's for.
Carson
A car slash bedroom.
Bubba Wallace
You're living in your car?
Leanne
Well, only part time.
Carson
And remember, it's her car, not his car.
Brooke
I have a headache, Leon. I'm sorry about that whole green flag thing.
Carson
No, it is a green flag. It's a green flag that he is such a good roommate that his ex doesn't even want to let him go. That's how awesome he is to live with.
Brooke
Dude, you share a bed that you guys rotate on the weekends.
Leanne
Hold on. We don't share the bed. When she's in it, I'm not. When I'm in it, she's not. We have a calendar. It's set up.
Brooke
The bed calendar. Organized community ticket. I can't say it, man.
Carson
Even Alexis is coming around on him now, so.
Brooke
Girls love you, bro.
Bubba Wallace
I mean, this is a nightmare.
Carson
It could be your nightmare if you say yes to another date with Carson. And we would pay for that date if you're open to it.
Brooke
It will be your nightmare if you say yes.
Jeffrey
No, it's not going to be your nightmare until it goes viral.
Carson
Yeah.
Brooke
Oh, yeah.
Bubba Wallace
I don't want this to go viral. I don't want to go on another date if you're.
Carson
Oh.
Jeffrey
If you're seeing this on socials, do not comment. Do not like this.
Carson
Oh, man, Carson, it sounds like a no from Leanne there.
Leanne
Oh, Leanne. You know, you didn't complain when I used the ex's debit card to pay for dinner.
Carson
Wait, you share that, too?
Brooke
Get out of here.
Bubba Wallace
You never told me that.
Brooke
How would it come up in conversation?
Carson
Yeah, all right, well, wow. I mean, Carson, you were worried that the problem was that you picked her up in your ex's car, and turns out the issue is that you actually swap beds with your exes because you live together.
Brooke
Oh, and your ex pays for everything?
Carson
Well, half of. Half of the time.
Leanne
I mean, when you say it like that, I think I sound like a pretty good dude.
Carson
Oh, you're a catch, buddy.
Brooke
Brooke and Jeffrey in the morning.
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Carson
I mean, dude, how did Carson think that it was okay to withhold that information from us in part one?
Jeffrey
Has he said a lot of information?
Carson
Cause Brooke literally asked him, what's your relationship with your ex? And he said, oh, we're still friends. Didn't mention, oh, yeah, we share the same master bed off of a rotating calendar. Would have been a little bit of a different story for us.
Brooke
Sorry, if you have a one bedroom apartment, you can't call it a master bed. It's the only bed.
Jeffrey
I didn't want the call to end because the more he's kept talking, the more codependent he is. He uses her debit card, her car, her house.
Brooke
Oh, I know. What else? Her clothes? No, the same toothbrush.
Jeffrey
I think we switch knives.
Carson
Wouldn't be surprised. But honestly, honestly, just be truthful with us up front. So Brooke doesn't come off looking as bad as she did.
Jeffrey
Yeah, and that poor girl didn't want this to hit the air. And now because of him, you know.
Carson
What'S going on, so. And that's why I just want to be honest right now with all of our listeners and tell you the truth, that we do have a second date podcast.
Brooke
Yes, it's real.
Carson
Somehow it gets millions of downloads every month. Even I did not believe that.
Jeffrey
Go look for yourself.
Carson
Brooke showed me the number, so if you want to check it out and subscribe.
Jeffrey
And Brooke always lies. Yes, she was really telling the truth.
Brooke
I don't lie.
Carson
It's a green. It's a green flag to listen to our podcast though. Binge away at Brooke and Jeffrey.
Brooke
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Alexis
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Jeffrey
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Brooke
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Podcast Summary: Brooke and Jeffrey: Second Date Update – "Lipstick Dipstick"
Episode Title: Second Date Update: Lipstick Dipstick
Release Date: August 1, 2025
Podcast Series: Brooke and Jeffrey: Second Date Update
Host/Author: iHeartPodcasts
In the August 1, 2025 episode of Brooke and Jeffrey: Second Date Update, hosts Brooke and Jeffrey delve into a compelling listener story titled "Lipstick Dipstick." This episode explores the complexities and unexpected challenges that can arise in the early stages of dating, particularly when past relationships intersect with new romantic endeavors.
The episode centers around Carson, a listener who recently went on a promising first date that seemed to be going well. Keen on securing a second date, Carson faced an unforeseen hiccup when his date discovered a lipstick canister in his car, leading to confusion and concerns about his relationship status. The incident raises questions about transparency and the potential red flags that can derail budding relationships.
First Date Success:
Leanne (Listener): "We went to the steakhouse. Things went really well. It was everything I hoped it would be." [06:23]
The Discovery:
Leanne: "She reached down, she pulled it out, and it was a canister of lipstick." [07:10]
Carson: "I borrowed my ex-girlfriend's car." [07:37]
Brooke and Jeffrey dissect Carson's situation, emphasizing the importance of honesty and clear communication in dating. They explore how Carson's decision to borrow his ex-girlfriend's car without full disclosure may have inadvertently cast doubt on his intentions and relationship status.
Brooke on First Impressions:
Brooke: "If you can be friends with an ex, it doesn't mean that you still have feelings for them. It's when you still have feelings that things get dicey." [14:31]
Jeffrey's Insight on Perception:
Jeffrey: "When you're driving her car, you're going to want to explain if it's better than saying you're still sleeping together." [09:11]
To provide clarity and resolution, Brooke and Jeffrey invite Leanne to join the show live. During the call, more layers of Carson's personal life are unveiled, revealing a complex living arrangement with his ex-girlfriend that goes beyond simply borrowing a car.
Revelation of Shared Living Space:
Leanne: "I do live with my ex. That's how I was able to borrow the car." [16:20]
Brooke: "A sister that you slept with?" [16:44]
Complex Living Arrangements:
Leanne: "We split the rent, we rotate the car. It's a good setup." [17:11]
Brooke: "You share the bed? That's a good living situation." [16:44]
As the conversation unfolds, Brooke and Jeffrey highlight several red flags in Carson's behavior, including financial entanglements and shared personal spaces with an ex. They stress the importance of setting boundaries and ensuring that past relationships do not interfere with new ones.
Brooke's Concern:
Brooke: "Why do you live with her?" [16:37]
Jeffrey: "He uses her debit card, her car, her house." [22:18]
Carson's Transparency Issues:
Carson: "I left something out." [21:50]
Jeffrey: "He was driving his ex's car, swapping beds, using her debit card." [22:25]
The episode concludes with a reflective discussion on the importance of honesty and boundaries in dating. Brooke and Jeffrey advise listeners to be upfront about their past relationships and current living situations to foster trust and avoid misunderstandings.
Brooke's Final Thoughts:
Brooke: "Be truthful with us up front. So Brooke doesn't come off looking as bad as she did." [21:36]
Jeffrey's Takeaway:
Jeffrey: "This whole setup is a disaster." [17:11]
This episode of Brooke and Jeffrey: Second Date Update serves as a cautionary tale about the complexities of modern dating, especially when past relationships are still intricately woven into one's present life. Through engaging discussion and real-life storytelling, Brooke and Jeffrey offer valuable insights into navigating the murky waters of second dates and beyond.
For more engaging and insightful discussions on dating and relationships, tune into the full hour-long show available on iHeartRadio, Apple Podcasts, and Spotify.