Second Date Update: First Time Tinderer

Summary

Podcast Summary: "Brooke and Jeffrey: Second Date Update" Episode: Second Date Update: First Time Tinderer
Release Date: February 19, 2025
Host/Author: iHeartPodcasts

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Introduction

In this engaging episode of Brooke and Jeffrey: Second Date Update, the hosts delve into the intricate world of modern dating through the lens of Rachel, a listener experiencing the dating app scene for the very first time. The episode provides a comprehensive exploration of her journey, the dynamics of her first date, and the subsequent challenges she's facing with ghosting. Through insightful discussions and real-time interactions, Brooke and Jeffrey offer both entertainment and valuable dating insights for their audience.

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Rachel’s First Foray into Online Dating (02:24 - 05:19)

Rachel, who had not dated since 2010 and was new to dating apps, reached out to the show to share her experience of meeting Jack through a dating platform. She describes the overwhelming nature of diving into the digital dating pool after a long hiatus.

Notable Quote:

• Rachel (02:37): "Like, ever. It's like a time warp."

Brooke introduces Rachel's story, highlighting her transition from traditional dating to app-based connections, setting the stage for a relatable discussion for many listeners navigating similar experiences.

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The First Date Experience (05:19 - 07:34)

Rachel recounts her first date with Jack, emphasizing the thoughtful gestures and the positive atmosphere they shared. Jack’s approach was described as gentlemanly and respectful, which initially boosted Rachel’s confidence in online dating.

Notable Quote:

• Jack (03:24): "So, like, I just completely new for me. And when I got flooded with all these guys, it was exciting. It kind of boosted my ego."

Rachel and Jack discuss their plans for the date, which culminated in a dinner outing facilitated by modern conveniences like Uber, marking Rachel’s first real in-person date after a decade.

Notable Quote:

• Rachel (04:53): "It's her first dating app. It's the first guy she's met on this. Like, I would be so nervous if I were you."

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Setting Boundaries: The Index Card Incident (07:34 - 14:18)

A pivotal moment in Rachel and Jack's date was when Rachel presented Jack with an index card outlining her physical boundaries. This unconventional method sparked a debate among the hosts and highlighted the importance of clear communication in dating.

Notable Quote:

• Jenny Garth (13:02): "First dates are supposed to be a little more chill and steer the conversation toward things that are maybe more fun and getting to know each other. And it was just basically at one point, I was like, look, I just want to get to know you."

The card included a structured timeline for physical interactions, which Jack found surprising and somewhat off-putting. The hosts explore whether this approach hindered the natural flow of the date and contributed to Jack's subsequent lack of communication.

Notable Quote:

• Dylan (13:51): "Wow."

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Analyzing the Aftermath: Ghosting and Mixed Signals (14:18 - 17:56)

Following the date, Jack ceased contact, leaving Rachel puzzled and seeking closure. The hosts engage in a detailed analysis of the situation, debating whether the index card was the primary reason for the ghosting or if other factors played a role.

Notable Quote:

• Jack (15:09): "We had such a great time. I mean, you're such a sweetheart. You just told me that you, like, you think I'm attractive. You know, I'm trying to be a great communicator. You know what I mean?"

Brooke and Jeffrey discuss the balance between setting personal boundaries and maintaining spontaneity in early dating stages. They emphasize the importance of reading social cues and ensuring both parties are comfortable with the pace of the relationship.

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The Call to Jack: Seeking Clarity (10:41 - 17:56)

In a bold and interactive move, Brooke and Jeffrey decide to call Jack live on air to gain his perspective on the first date and the reasons behind his silence afterward. Jack explains his side, expressing confusion over Rachel’s extensive boundary setting and asserting that he felt the chemistry was lacking despite initial positive interactions.

Notable Quote:

• Jack (15:45): "It's just, even though I think you're a great person, you are clearly physically attractive, and it's just like the chemistry was just not there."

The live call serves as a dynamic pivot in the episode, offering listeners firsthand accounts and fostering a transparent dialogue about dating challenges. Rachel is encouraged to approach Jack for a possible second date, emphasizing the potential for growth and understanding.

Notable Quote:

• Rachel (17:56): "Maybe you could just change a few things. She's funny. She's funny, Jack."

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Conclusion and Takeaways (17:56 - 18:19)

The episode wraps up with reflections on the importance of open communication, understanding personal boundaries, and the adaptability required in the evolving landscape of dating apps. Brooke and Jeffrey encourage listeners to remain positive and proactive in their dating endeavors, highlighting Rachel’s experience as both a cautionary tale and a beacon of hope for new daters.

Notable Quote:

• Dylan (18:05): "Yeah, just don't say that code word that makes her cry."

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Key Insights

• Communication is Crucial: Clearly articulating personal boundaries can prevent misunderstandings but may also hinder the natural progression of a relationship if not approached delicately.

• Adaptability in Dating: Transitioning from traditional to digital dating requires flexibility and a willingness to embrace new methods of meeting and connecting with potential partners.

• Balancing Structure and Spontaneity: While structure in dating can provide clarity and safety, it's essential to balance it with spontaneity to foster genuine connections.

• Overcoming Ghosting: Understanding the reasons behind ghosting and addressing them openly can lead to closure or the opportunity to rekindle interest.

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Notable Quotes with Timestamps

• Rachel (02:37): "Like, ever. It's like a time warp."
• Jack (03:24): "So, like, I just completely new for me. And when I got flooded with all these guys, it was exciting. It kind of boosted my ego."
• Rachel (04:53): "It's her first dating app. It's the first guy she's met on this. Like, I would be so nervous if I were you."
• Jenny Garth (13:02): "First dates are supposed to be a little more chill and steer the conversation toward things that are maybe more fun and getting to know each other. And it was just basically at one point, I was like, look, I just want to get to know you."
• Dylan (13:51): "Wow."
• Jack (15:09): "We had such a great time. I mean, you're such a sweetheart. You just told me that you, like, you think I'm attractive. You know, I'm trying to be a great communicator. You know what I mean?"
• Jack (15:45): "It's just, even though I think you're a great person, you are clearly physically attractive, and it's just like the chemistry was just not there."
• Rachel (17:56): "Maybe you could just change a few things. She's funny. She's funny, Jack."
• Dylan (18:05): "Yeah, just don't say that code word that makes her cry."

---

Conclusion

This episode of Brooke and Jeffrey: Second Date Update offers a nuanced look into the challenges of modern dating, particularly for those re-entering the scene after a long hiatus. Through Rachel’s story and the live conversation with Jack, listeners gain valuable insights into communication, boundary-setting, and the emotional complexities of forming new romantic connections in the digital age. The blend of personal anecdotes and expert commentary makes for a rich and engaging discussion, resonating with anyone navigating the unpredictable waters of dating.

Transcript

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[Jeff]

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[Eddie]

Download the app today.

[Rachel]

High Five Casino okay, we just need to apologize right now for taking over your TikTok for you Paige yeah, sorry. Not sorry. My God. Yes, all the old ones are going viral but the new ones are so much better. Okay. I'm so glad you found them. Follow, like, whatever you're supposed to do on these podcasts and just sit back and listen.

[Brooke]

Second date update. You know, we've talked about people getting back into the dating game after being out of it for a while, but we don't normally speak to people on this segment who are using dating apps for the very first time.

[Rachel]

Like, ever.

[Brooke]

Ever. It's like a time warp.

[Rachel]

Yeah.

[Brooke]

If you haven't dated since 2010 and you met somebody at a grocery store nowadays, you're getting an eggplant. All right. But it's a digital one, and I don't know if you even wanted it in the first place. But that's what happened with Rachel recently. She emailed us saying this is her very first time being on a dating app, and she actually met a great guy who's somehow not calling her back. So. Rachel, welcome.

[Jack]

Hey, thanks for having me.

[Rachel]

I'm just curious because I've never been on dating apps.

[Brooke]

Right.

[Rachel]

Because I met my husband, like, before. They were huge.

[Dylan]

Oh, yeah.

[Rachel]

Like, what is it like for your first time?

[Jack]

Well, it made me feel kind of old, too, though. I mean, yeah, I had been in a relationship since college, so, like, 2007. You know what I mean?

[Rachel]

Yeah.

[Jack]

So, like, I just. Completely new for me. And when I got flooded with all these guys, it was exciting. It kind of. It boosted my ego. But it took me about, like, two and a half weeks to find someone that actually fit all of my criteria. And that was Jack. Yeah.

[Rachel]

So you messaged him.

[Jack]

So he reached out to me at. So I thought that was vulnerable. You know what I mean? Like, that's pretty hardcore. And not at all.

[Brooke]

But thousands of other guys did, but it's okay.

[Dylan]

He said, hey, like, oh, my God, he's so formal, so confident.

[Rachel]

I mean, how long did it take you to go out with him, like, between talking to him on the app and then the actual date?

[Jack]

Actually, about five days. So we started kind of like Sunday, Monday talking, and then that weekend, he was free and I was free, so. Nice.

[Rachel]

I feel like a weekend date is a big commitment date. I don't know, like, using your weekend for that.

[Dylan]

I'll take a date any day of the week.

[Brooke]

I think single people think anytime is a good time. Married people. Like, my weekend is my only time. So what did you guys end up doing? Rachel?

[Jack]

So we ended up going to dinner.

[Rachel]

Okay.

[Jack]

It was really, really sweet. We. We met there. So I took an Uber.

[Rachel]

And what. What was that like for you? Because it's like your first dating app.

[Brooke]

An Uber ride. You've never been in an Uber. Technology's amazing.

[Dylan]

They can deliver food.

[Rachel]

It's her first dating app. It's the first guy she's met on this. Like, I would be so nervous if I were you. Just because, God, that's a lot. It's a lot.

[Jack]

I'm a huge fan of Broad City and I felt like I was in Broad City.

[Rachel]

What was the actual date like?

[Jack]

Oh, well, he was just such a gentleman. Like, he was dreamy. He was such a good listener to you guys.

[Dylan]

Oh, that's important.

[Brooke]

He was what?

[Dylan]

Yeah, yeah, it's important.

[Rachel]

Did your ex come up a lot? Because, I mean, you did mention to us that you were together for a really, really long time.

[Jack]

It did, because like I said, it was over a decade. And each thing that came up, he seemed to roll with it. And it didn't seem to bother him. I mean. Cause here's the thing, I was upfront with him from the get go and I told him straightforward, that I'm not going to go home with him.

[Brooke]

Oh, this is like immediately after the handshake or when is this.

[Jack]

This was like after the first appetizer because I wanted to kind of loosen things up, but I just didn't want to get too loose, if you know what I mean.

[Dylan]

But that also sounds good. You want to set boundaries and he should respect boundaries.

[Rachel]

It could also come across as rude, though. Like, you're also a assuming that that's all that he's looking for.

[Brooke]

You know, like, Brooke's only saying that because she never would have said that to a guy. Those words have never crossed her lips.

[Dylan]

She's like, I'm surprised you haven't slept.

[Rachel]

So we finished the first nap. Is it time? He could have been insulted by that.

[Brooke]

What was his reaction? Were you able to gauge it?

[Jack]

He was taken aback, but he said he wasn't expecting anything. So maybe like you said, it just kind of threw him off or whatever. And I mean, here's the thing. When you talked about bringing up my ex for the first time, I didn't. I didn't cry, guys. You know, I was on the date.

[Rachel]

Oh, honey, I'm glad.

[Jack]

I mean, I teared up whenever I think of Dylan. You know, that's my. My ex.

[Dylan]

And I'm sure I'm with you. It's been fun. I know I've been broken up.

[Brooke]

I hear Rachel crying right now. Even just mentioning him, that's hard.

[Rachel]

You probably were still emotional then. If you're just like just now, not crying, talking about Him.

[Jack]

I think maybe that the drinks didn't help, you know?

[Rachel]

Do you think that that's why Jack isn't calling you back?

[Jack]

I don't think so. No, he was like I said, he didn't feel like. He didn't seem like he was weirded out by it at all. And. No, it seems fine.

[Dylan]

We all know you obviously didn't hook up, but did you guys like kiss or hug or like do anything else that's like intimate?

[Jack]

No, we. He was a gentleman, so we did like this side hug thing.

[Rachel]

The side hug, like I do with all my friends. Like a one armed hug.

[Dylan]

Okay.

[Rachel]

I don't know that that's a good sign.

[Jack]

It was my first date. Like I haven't been in a real in person date in over a decade. Like, give me a break.

[Brooke]

Yeah, we're used to side tongue on this, so we're just.

[Jenny Garth]

Sorry.

[Brooke]

We've heard a lot of dating stories, but yours sounds very nice, especially for your first time back into the dating pool. First time on a dating app. So let' let's play a song. We'll give. Not Dylan.

[Rachel]

Jack.

[Brooke]

Jack.

[Rachel]

Excuse me.

[Brooke]

I am so sorry. I promise you, Rachel, I will not call him Dylan.

[Rachel]

Okay.

[Brooke]

In fact, this is going to be the last time I ever say Dylan on this show.

[Rachel]

You just said it again.

[Brooke]

Okay, sorry.

[Dylan]

All the Dylan's out there.

[Brooke]

Play a song, we'll come back and we'll call Jack for you. Not Dylan. Right after this second date, we'll be.

[Dylan]

Dylan is number. Dialing his number.

[Brooke]

Yeah, sorry.

[Dylan]

Coming up.

[Brooke]

Second date date. If you're just joining us for the second date, we're talking to Rachel, who went on her first. First date in a very long time. Yeah, she said it's been more than a decade since she's gone on one and she's never been on a dating app before. This was her first time on a dating app and that was a little bit overwhelming, which is understandable.

[Dylan]

Totally.

[Brooke]

In fact, I'm going to do an impression right now of a guy seeing fresh meat on a dating. Let's take the music down. Oh, yeah. Oh, a newbie. We're going to stay at Applebee's for 20 minutes and then go back to my mom's house and she's going to watch me play Mario Kart.

[Rachel]

Oh, man. So it's like she was dating in college all over again.

[Brooke]

Jack, who she met, wasn't like that. He was different. He was a gentleman. And how do I know that they were a good match? Because Rachel said she didn't cry once during their entire date.

[Rachel]

Cry about her ex?

[Brooke]

Well, cry in general. No tears. That's love. So, Rachel, we're about to give Jack a call. How are you feeling?

[Jack]

Honestly, I'm. I'm hoping for the best. There was nothing but positive vibes, so I feel like something happened, maybe at his job or family. I don't know. I hope everything's okay, but he's just perfect.

[Rachel]

And also, it's like, you know, this is new to you. There's a lot of options out there that you haven't even explored.

[Brooke]

Here it is. Here's Brook's pep talk to go out on the town and sleep around.

[Rachel]

That's how you get over people. People.

[Dylan]

Joe, there is one thing that doesn't change in dating, and that's vibes. Like, you can tell if something happened on the date. You can pinpoint a moment usually. So if you don't feel like there was something, then maybe there wasn't.

[Rachel]

She hasn't even really dated in her adult life. I mean, you've had the same boyfriend since you were in college. You know, like, just want you to make up for lost time, but.

[Brooke]

Okay, let's call Jack. You know what? We're just going to stop projecting our feelings and our failed relationships onto you. We're just going to dial Jack and see what he has to say. Okay?

[Jack]

Okay.

[Rachel]

Okay.

[Brooke]

Here we go.

[Jenny Garth]

Hello?

[Brooke]

Hey, is this Jack?

[Jenny Garth]

Yeah, this is Jack. Who's this?

[Brooke]

Hey, Jack. My name is Jeff from the radio show Brooke and Jeffrey in the Morning.

[Rachel]

Hello?

[Brooke]

Oh, that's my co host, Brooke, who just jumped in with a weird voice.

[Rachel]

No, it just sounded like how he was hitting on us when he answered the phone, so I was, like, returning the favor. Jack. Oh, yeah, I just think it's interesting because, like, it was an unknown number, Right? Were you expecting someone else on the phone? Jack?

[Jenny Garth]

I'm sorry. What is this all about?

[Brooke]

Yeah, no, I'm sure you're very confused. This lady is talking at you and kind of hitting on you at the same time. We're a morning radio show, and we're doing a segment called A Second Date Update where we're trying to help one of our listeners get in touch with you after you went out.

[Jenny Garth]

Oh, geez.

[Brooke]

Sounds like fun, right?

[Jenny Garth]

All right, what do you need from me?

[Rachel]

Well, we heard a lot of good things about you, so that's a good start.

[Brooke]

And we heard them from one of our listeners named Rachel.

[Jenny Garth]

Oh, okay.

[Brooke]

Yeah, yeah. So tell us what you thought about Rachel.

[Jenny Garth]

I mean, Rachel was. She's cool. She's nice.

[Rachel]

Was she attract? I mean, were you attracted to her? Did you feel like you guys had some chemistry?

[Jenny Garth]

Yeah. You know, I think she's beautiful. She's really cool, and I think maybe she's just going through a lot right now and working through stuff, but.

[Brooke]

What do you mean?

[Jenny Garth]

I was not prepared to talk about this.

[Rachel]

It's okay. I mean, she told us some stuff about, like, her ex and maybe how she talked about that on the date.

[Brooke]

She said a lot of really nice things about you, about how you're a.

[Rachel]

Great guy and a good listener. She said you're a great listener.

[Jenny Garth]

Well, that's super nice of her. She was just really specific about what she wants in a guy and kind of went on and on about how I fit those things.

[Rachel]

And that was. That wasn't good to you?

[Jenny Garth]

I mean, it's nice. It is nice. I think it was just, like, a little much at some point.

[Brooke]

What was much?

[Jenny Garth]

Like, I don't know. First dates are supposed to be a little more chill and steer the conversation toward things that are maybe more fun and getting to know each other. And it was just basically at one point, I was like, look, I just want to get to know you. And she smiled, and she reached in her purse and handed me an index card.

[Rachel]

Okay, what was on the index card?

[Brooke]

Index cards are sexy.

[Rachel]

Who has index cards? Is it a recipe from her grandma or something?

[Jenny Garth]

I kind of wish it was. On top, it said physical boundaries and kind of listed all these physical things that she would allow. And she also listed them by date.

[Rachel]

Oh, you mean like. Like first kiss, three dates in. You can touch my butt. Four dates.

[Jenny Garth]

Exactly. It.

[Dylan]

Wow.

[Brooke]

Really?

[Dylan]

Oh, my gosh.

[Rachel]

A lot of planning.

[Brooke]

Do you have the card?

[Jenny Garth]

Yeah. Oh, yeah. Date one, fist bump. Fist bump, side hug, and high five.

[Dylan]

Oh, my God.

[Brooke]

I wouldn't even show up.

[Dylan]

Send me the card before the date.

[Rachel]

From.

[Brooke]

From what we heard, it sounded like you did that side hug on the first date.

[Dylan]

Yeah.

[Jenny Garth]

Oh, yeah. Yeah, we definitely. We did actually. We did do the side hug.

[Brooke]

Yeah.

[Jack]

How?

[Brooke]

Was.

[Jenny Garth]

Was exactly what you'd expect from a side hug.

[Eddie]

Okay.

[Dylan]

Okay.

[Brooke]

All right.

[Rachel]

So it wasn't necessarily her boundaries. It was the way they were presented. Is that what you're saying?

[Jenny Garth]

I think it's cool. Like, her therapist says, always create boundaries, which she told me, you know, And I think it's super healthy. That's great, but it's just not what I'm looking for. It's just a little much to me, and especially talking about on the first date like that, you know, maybe there's.

[Rachel]

A more organic way to work in your boundaries rather than a five by seven.

[Brooke]

Like, what's more organic than having her be on the radio with you and tell her her boundaries right now? Because she's been on the other line listening, Jack, and she wants to talk to you.

[Jenny Garth]

No.

[Rachel]

Yeah. No, she's not respecting your boundary in that way.

[Brooke]

Rachel.

[Jenny Garth]

Oh, no, Jack. Oh, my God.

[Jack]

We had such a great time. I mean, you're such a sweetheart. You just told me that you, like. You think I'm attractive. You know, I'm trying to be a great communicator. You know what I mean? Like, no gray areas. I thought you would appreciate to know exactly what I want, what I needed. You know, Like, I'm. I'm not. I'm not trying to play games.

[Rachel]

Yeah, that's a hot pitch right there. I liked it.

[Brooke]

Jack, feel free to respond.

[Jenny Garth]

Rachel. Rachel. Okay, look, this is a. I can't believe you're on. We're on the radio right now. This is ridiculous. I know.

[Brooke]

Ridiculous is a little offensive to me.

[Jack]

Yeah, I think it's very offensive.

[Jenny Garth]

It's just, even though I think you're a great person, you are clearly physically attractive, and it's just like the chemistry was just not there, you know? And, like, the way this. This whole boundary note card thing was. Was brought up, it just kind of killed the vibe and. I know. Maybe.

[Brooke]

Do you know how many times a note card would have saved me on one of my Craigslist meetups? Whether or not, like, you think it's if it's going too far or it's like, taking the spontaneity out of it. She's just trying to show you what she's comfortable with doing before things get awkward.

[Dylan]

But your car, by the hour. I think she's over the second hour.

[Brooke]

I mean, Rachel, it's date in a really, really long time. So she's just trying to get her feet back under her.

[Jenny Garth]

It doesn't mean you need to be a robot, though. It's like when I walk into your car, I have to pull out the note card and check what I can do. If it's like, side hug or small.

[Jack]

You said we didn't have any chemistry, but I guarantee that server would have told you different. And to be honest, it's your loss, because after date number five, things really open up.

[Rachel]

Was that on the card? No. I mean, the thing about Rachel, she sounds like someone who's very organized and maybe very different from you and could really bring some other aspects to your life that you don't have right now.

[Brooke]

Let's get to the second day on your note card so we can get to some of that other stuff, because we'd like to pay for that. Hey, what do you say, Jack? Give it another shot.

[Dylan]

Lock it up.

[Jenny Garth]

Rachel, I just. I think it's cool that you think we had chemistry. I just think that, like, a lot of the fun was kind of drained out of it as soon as those boundaries came up and.

[Rachel]

Come on, give her a second chance on the second date. She knows that already. She doesn't have a second note card. Do you, Rachel? You have another note?

[Jack]

Not anymore. No pencil.

[Rachel]

Maybe you could just change a few things. She's funny. She's funny, Jack.

[Jenny Garth]

All right. You know, if we can start over. If we can start over.

[Dylan]

It'S like a punch card. You're gonna get, like, a free latte.

[Rachel]

So are you just saying yes? Is that what you're saying, Jack?

[Jenny Garth]

I mean, yeah, okay, I'll say yes, but I'll pretend like the card never happened.

[Dylan]

Okay?

[Rachel]

She still wants you to remember the boundary. Still respect her.

[Jack]

Zach, I'm actually excited. And I'm really happy that I was vulnerable and called the station. Thank you, guys.

[Brooke]

You barely cried once during this entire call. That must mean it was a positive experience.

[Dylan]

Yeah, just don't say that code word that makes her cry.

[Brooke]

It's Dylan. Oh, God.

[Rachel]

Brooke and Jeffrey in the morning.

[Eddie]

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[Eddie]

You know more about the PayPal debit card than you did at the start of this podcast. You know that the PayPal debit card gives you the ability to pay everywhere. You know that you earn 5% cash back on a category of your choosing on up to $1,000 of monthly purchases. And you know that you get to pick a new category every month. Apparel for back to school. Groceries for the holidays. Start earning 5% cash back with the PayPal debit card today. Don't just pay. PayPal terms apply. See PayPal app. This card is issued by the Bancorp Bank N.A. pursuant to license by MasterCard International, Inc.

[Brooke]

Clorox Sentiva Smells like lavender.

[Eddie]

Cleans like.

[Brooke]

Clorox, and feels like hmm.

[Rachel]

All right.

[Ashley Kinetic]

That could go on for a while.

[Rachel]

Experience the long lasting freshness of Clorox Centiva.

[Ashley Kinetic]

Now available in Clorox Scentiva Lavender Scented Bleach.

[Brooke]

Use as directed.