Second Date Update Classic: Due the Math

Summary

Podcast Title: Brooke and Jeffrey: Second Date Update
Episode: Classic: Due the Math
Release Date: January 11, 2025
Host/Author: iHeartPodcasts

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Introduction to the Episode

In the "Classic: Due the Math" episode of Brooke and Jeffrey: Second Date Update, hosts Kat Dennings and Jeffrey delve into the complexities of modern dating through the lens of mathematical compatibility. The episode spotlights Justine, a listener who recently experienced a unique first date that ended unexpectedly, leading her to seek a "Second Date" with the help of the show.

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Justine's Story: The Dating Math

[02:33 – 05:01]

The episode begins with Justine sharing her experience of using an online test designed to calculate compatibility based on personal preferences. As Justine explains, "It's like this online test. You put in all the stuff that you care about, like your preferences and whatever for, like, finding a partner, and it's supposed to come back with, like, the percentage of men on dating apps who, like, fit those preferences." Despite her seemingly reasonable criteria—such as valuing a partner with a job and independence—the test returned a disheartening result: less than 1% of men matched her preferences.

---

The Meeting with James

[04:42 – 06:18]

Against the bleak statistics, Justine recounts meeting James serendipitously at a coffee shop. Instead of through a dating app, James approached her with an unconventional "boyfriend application" line: "Are you accepting applications?" Initially perplexed, Justine was amused when James produced a "dating resume," listing his interests and experiences. She shares, "He legitimately, like, pulled out a piece of paper."

James extended the interaction by offering to Venmo her for the coffee she had already purchased, demonstrating his considerate nature. This creative approach set the stage for what seemed like a promising connection.

---

The Interview Approach

[06:18 – 07:10]

Justine decided to take the dating interview seriously, leveraging her professional experience to ask James thoughtful questions, such as, "What's one thing you don't want me to know about you?" James responded candidly, revealing a personal vulnerability: "I cry when I watch the Matrix because I'm scared about the future." This honesty impressed Justine, who found his response both funny and genuine.

---

Ghosting After the First Date

[07:49 – 08:18]

Despite the positive interaction, Justine notes that James never followed up after their initial meeting. She mentions, "he never called me again," even after she jokingly suggested setting up a second interview. Attempts to reconnect through text were met with silence, leaving Justine both puzzled and disappointed.

---

The Second Date Update: Inviting James

[11:07 – 16:54]

Determined to uncover the reasons behind James' disappearance, Kat and Jeffrey decide to bring James onto the show for a "Second Date Update." They reach out and successfully connect with him, initiating a live conversation.

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Interview with James: His Dating Resume Approach

[11:21 – 17:45]

During the interview, James explains that his practice of using dating resumes is a well-honed strategy aimed at making meaningful connections. He admits to having approached numerous women with this method: "I've done that a good amount."

James shares anecdotes of diverse responses, including interactions with an "extreme couponer" and a woman obsessed with alien abductions, highlighting the varied reactions his approach elicits.

When discussing his interaction with Justine, James reveals that her quick wit and out-of-the-box thinking "freaked him out." He admits, "I didn't know how to respond," indicating that Justine's sharpness caught him off guard. This encounter marked a turning point for James, making him consider the possibility of a genuine connection beyond his usual tactics.

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Insights and Conclusion

[17:46 – 18:28]

Kat and Jeffrey analyze James' approach, questioning its efficacy and long-term viability. They humorously speculate about James potentially applying to "multiple boyfriend positions" across the city due to the scalability of his method.

The episode concludes with an invitation for James and Justine to embark on a "second interview," transitioning their interaction from a staged date to a more authentic connection. This move underscores the show's commitment to not only entertain but also facilitate real-life relationship developments.

---

Notable Quotes with Timestamps

• Justine on the Perfomance of the Dating Math Test:
  "It's supposed to come back with, like, the percentage of men on dating apps who, like, fit those preferences."
  [03:47]

• James Explaining His Approach:
  "I've done that a good amount."
  [12:16]

• Justine on the Outcome of Their Interaction:
  "He never called me again."
  [07:49]

• James Reflecting on His Interaction with Justine:
  "I never take this thing seriously. It's just sort of a gimmick."
  [13:44]

• Kat on James' Challenge:
  "Can you try to say it a little more assertive?"
  [16:31]

---

Final Thoughts

"Classic: Due the Math" offers a humorous yet insightful exploration of the intersection between modern dating strategies and personal connections. Through Justine and James' stories, the episode highlights the unpredictability of human relationships and the challenges of finding genuine compatibility in an increasingly algorithm-driven dating landscape. Kat and Jeffrey effectively balance humor with heartfelt moments, making this episode both entertaining and relatable for listeners navigating their own dating experiences.

Transcript

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[Kat Dennings]

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[Kat Dennings]

I was 18. The double bird was how I ended all our conversations.

[Ryan Seacrest]

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[Kat Dennings]

Can we try to talk to each other like rational adults?

[Tim Allen]

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[Ryan Seacrest]

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[Unknown]

Sephirah Season two is coming to Apple tv. What you all did five months ago was one of the most painful moments in the history of this company.

[Justine]

Our message got out.

[Unknown]

We're famous.

All of us equally.

Or one of us is like the star.

[Justine]

What did you see?

[Unknown]

My audi's wife was Ms. Casey.

[Tim Allen]

If you want to find out what.

[Kat Dennings]

Happened to her, I'll help.

[Unknown]

She's still a I want to see my wife. You should have left severance. New season streaming January 17th only on.

[Kat Dennings]

Apple TV plus okay, we just need to apologize right now for taking over your TikTok for you page. 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.

[Unknown]

Second date update. Is there any way to do the math to figure out what type of person you're the most compatible with?

[Kat Dennings]

Is there math for that?

[Unknown]

Oh, I'm better than math, too.

I'm never gonna find, like, start with affectionate.

[Kat Dennings]

Okay.

[Unknown]

Multiply by heavy petting, subtract two blindfolds, keep one, divide with an overbearing mother, and.

[Kat Dennings]

Oh, this is Jeff math. I get it now.

[Unknown]

You're gonna die alone.

[Kat Dennings]

Okay, shoot.

[Unknown]

Every time I try to calculate this, I keep coming up with the same answer.

Simple.

[Kat Dennings]

It's like time zero anytime you add the mother.

[Unknown]

Right?

Yeah, that's exactly it.

Thank goodness our listener Justine found a different formula, and hopefully her results are better than mine because apparently she's been single for a bit now. But, Justine, how's the dating world going for you? Are you also reserving a burial plot for one?

[Justine]

Yeah.

[Unknown]

Okay.

[Kat Dennings]

Okay, I can hear you. I can hear you laughing through the tears, so that's good. It's all right, Justine.

[Unknown]

But I haven't put my deposit down.

[Kat Dennings]

The funny thing is, you're not alone in that.

[Unknown]

A lot of us are out there with you. But you said that you figured out some sort of mathematic formula to help you with your dating life. What was that?

[Justine]

Yeah, it's like this online test. You put in all the stuff that you care about, like your preferences and whatever for, like, finding a partner, and it's supposed to come back with, like, the percentage of men on dating apps who, like, fit those preferences.

[Kat Dennings]

Oh, really? So wait, they also take the test then, or. No, I think that it probably. I'm guessing it's an algorithm that goes through and looks at their dating profiles. Is that how it works?

[Justine]

Yeah. Yeah. And so, like, I started out, like, super basic. I was like, they have to have a job. They have to, like, not live at their parents house. Like, have a car.

[Unknown]

Like, standards are crazy on your end.

[Justine]

I didn't put a single thing that was physical, like height or anything, and it came back with less than 1% of men. Just a car and a job, truly.

[Unknown]

Oh, my goodness.

[Kat Dennings]

Okay, so. So you weren't feeling positive? I'm guessing at that number.

[Justine]

Or, you know, that's like very bleak.

[Kat Dennings]

Okay.

[Unknown]

Yeah.

[Justine]

Anyway, I, like, after all of that, ended up meeting this guy named James, like, just in a coffee shop.

[Kat Dennings]

Oh.

[Unknown]

Didn't even need the dating app.

[Kat Dennings]

She ran into the 1%.

[Unknown]

Okay.

Kind of funny. Like, the irony.

How did that interaction happen?

[Justine]

I literally was just sitting down and I was, like, scrolling, and he comes up to me and he's like, are you accepting applications? And I'm like, oh, I'm sorry. I don't work here. Like, I thought he was, like, playing at the coffee shop.

[James]

Okay.

[Unknown]

Were you wearing, like, a. An apron or something?

[Justine]

No, I guess I just, like, looked like I was. I don't know. I don't know.

[Unknown]

Barista vibes or.

[Kat Dennings]

You're a manager, you know, sometimes you walk into a restaurant or something, you see a manager.

[Unknown]

That's a good point.

[Kat Dennings]

Yeah.

[Unknown]

How did you respond to him when he asked about application?

[Justine]

I was like, oh, sorry, I don't work here. And he was like, no, no. Like, to be your boyfriend.

[Kat Dennings]

Oh, it was all a line. Okay. Did you like that?

[Justine]

I mean, I thought it was funny, but he, like, fully went along with it, and he was like, listen, I brought my resume. I've got, like, my history and experience. And he legitimately, like, pulled out a piece of paper.

[Unknown]

Wait, what?

[Kat Dennings]

He had a dating resume?

[Justine]

Yes.

[Kat Dennings]

Oh, I have to know what was.

[Unknown]

On it, or is it a move that he pulls on women all the time and he has, like, 20 quote unquote dating resumes in his pocket to hand out whenever he sees someone cute?

[Kat Dennings]

Kind of like the real world of getting a job. If she liked the resume, who cares how many other people like what was on it?

[Justine]

You know, like, basic stuff. Like, he likes going to games and hiking, but he was like, yeah, if you want to set up an interview, can just, like, call the number? And I was like, why don't you just sit down now when I can interview you? Oh, my God.

[Kat Dennings]

Great response.

[Justine]

Yeah. And it was really nice. Like, he turned out to be an awesome guy. He, like, offered to literally Venmo me for the coffee that I'd already bought.

[Unknown]

What a good guy.

You look poor here. You probably need this money.

[Kat Dennings]

What was. What was the hardest boyfriend interview question that you asked him?

[Justine]

Well, okay, so I've actually, like, done interviews at my real job. So I was like, okay, I'm just gonna pull some of these. And I was like, what's one thing you don't want me to know about you?

[Unknown]

You're actually good at this.

I like it.

[Kat Dennings]

Dude, he is so not prepared for this.

[Unknown]

Dang it. I would hate that question to be asked to me on a first day. But did he have an answer for you?

[Justine]

He did. And it was like. It was, like, ready made. It's like he expected it. And he legitimately said, I cry when I watch the Matrix because I'm scared about the future.

[Kat Dennings]

Oh, I don't think that was prepared. I feel like that was honest.

[Unknown]

Yeah.

It seems so obscure. There's no way he just thought of that.

How did you feel about that response?

[Justine]

Honestly, I thought it was really funny, and it was really clever. And, like, because it was so quick, I was like, oh, no, you're serious? Yeah.

[Unknown]

Yeah. It's not a red flag to you that he thinks the Matrix is actually gonna happen in the next few years?

[Kat Dennings]

There could have been so many worse answers. He said, like, yeah, that is so much better than any.

[Unknown]

Okay.

[Justine]

So anyway, at the end, he's like, so, did I get the job? And I was like, well, we probably should set up, like, a second interview. And then he's like, oh, then I definitely got the job. And we kind of, like, left it off there, and it was funny, and we laughed. And then he, like, never called me again.

[Kat Dennings]

What? Weird.

[Justine]

I, like, texted him, made jokes about, like, hey, we need to set up your second interview. And it was just silence.

[Unknown]

Did you guys kiss or anything? Or, like, hug? Was there a physical vibe?

[Justine]

No.

[Unknown]

Yeah, like a normal job interview. Yeah.

[Kat Dennings]

I was gonna say. What?

[Unknown]

It's not a real job interview.

[Kat Dennings]

It doesn't sound like a transition.

[Unknown]

How do think I got hired here?

[Kat Dennings]

That's true. I mean, that is strange, though, because he's the one that approached you. Yeah, he's the one that did the line. Like, why wouldn't he?

[Unknown]

But she's the one that took it to the next level, that actually made him sit down for it. He probably just thought it was a smooth line and was going to back away.

[Justine]

So he literally was the one asking, like, did I get the job?

[Unknown]

Yeah, yeah. He just wants the ego boost. He doesn't ask to accept the offer.

The company gives you isn't good.

[Kat Dennings]

Or he's got to put in two weeks at his last job.

[Unknown]

So.

He'S, like, engaged.

[Kat Dennings]

We got to find out.

[Unknown]

Yeah, Good. Clearly a lot of options on the table. We're gonna find out for sure what happened when we come back. And call James to do your second date update. Right after this Second date update, is there any setting more romantic than a job interview?

[Kat Dennings]

Oh, yes.

[Unknown]

Many, many, many.

[Kat Dennings]

It shouldn't be romantic.

[Unknown]

I don't know, Brooke.

[Kat Dennings]

I think HR Does.

[Unknown]

You're dressed all nice. You're talking about your biggest strengths and your greatest weaknesses. Okay. All of A sudden what? Pants.

[Kat Dennings]

Oops. Oh, God.

[Unknown]

A resume.

[Kat Dennings]

No.

[Unknown]

Would you look at that? I just happen to have that on me.

[Kat Dennings]

Why is it no wonder it's so warm.

[Unknown]

That's actually kind of what happened to one of our listeners who met a guy recently. It wasn't an official job application, but some dude saw at a coffee shop and asked, hey, are you taking boyfriend applications?

[Kat Dennings]

It is so smooth.

[Unknown]

And he even had a resume in his pants.

That's why it's even in his pocket.

[Kat Dennings]

Okay. Or who knows where it was? We don't know.

[Unknown]

Either way.

It's kind of sus that he just carries that around, waiting to whip out to any cute girl, if that's what he does.

But we don't know. He may have done this.

[Kat Dennings]

Just here's the thing. At least he's putting some effort in.

[Unknown]

Yeah, it did work. And he got to sit down with her for a little interview, slash, mini first date. By the end, he said he was definitely going to call her. And according to her, he definitely didn't.

[Kat Dennings]

Ah.

[Unknown]

So, man, I think we're all a little bit concerned that this little shtick he's doing is working too well. And maybe he's applying to multiple boyfriend positions all throughout the city.

[Kat Dennings]

There are a lot of openings. Yeah, there's a lot. So not a lot of good candidates. Yeah.

[Unknown]

Justine, if this turns out where he actually does this all the time and meets hundreds of women this way, how could we make him remember you and have you stand. Like, how do we identify you? Or do you still even want to go out with him at that point?

[Justine]

Well, at least I'm curious to hear what he has to say, but, yeah, I was wearing a green romper. I have red hair and glasses.

[Kat Dennings]

Okay. Cute. I feel like you were the only one that sat him down and actually gave him, like, a legit interview. Yeah, I mean, like, how could he not remember you? Hopefully.

[Unknown]

Yeah.

Yeah.

So we'll see if he does remember you and what he has to say. We're going to dial James's phone number right now. Here we go.

[James]

Hello?

[Unknown]

Hey, we're looking for James.

[James]

Yeah, this is him. Who's this?

[Unknown]

Where we. We are a radio show.

Jeff. Sorry, what? You fumbled, like, first word.

Yeah, thanks for pointing out all my flaws in front of everybody.

[Kat Dennings]

You know, if you were interviewing for.

[Unknown]

This job, we're calling on behalf of our boss, Justine, and apparently you applied for the position of her boyfriend role recently.

[James]

Oh, okay.

[Kat Dennings]

Yeah, yeah. You remember that interview? Do you remember that interview?

[James]

I. I mean, I. I remember A few of them, yeah.

[Kat Dennings]

You're on to something there. That's all right, though. I mean, we expected that. Yeah.

[Unknown]

We heard about the move that you pulled on our listener, where you walked up to her and you, like, had a resume and asked if there was a boyfriend opening. Is that something that you've done a lot?

[James]

Yeah. Yeah, I've done that a good amount.

[Unknown]

Can I. Can I guess? How many times is it? 200 times?

So many.

[James]

There's no way I. I don't know about 200.

[Kat Dennings]

I want to know the success rate. How many of those turn into a date?

[James]

They do sometimes. I've definitely met some interesting people.

[Unknown]

Okay. I am curious about that before we get to, like, Justine specifically. Like, what are some of the quirky things that you found out while trying this on other people before?

[James]

I mean, there was this one girl who was an extreme couponer. Oh, whoa. I've never met before.

[Unknown]

Yeah, that's interesting. There are TV shows about people.

[James]

Yeah.

[Unknown]

We call them cheapskates, but, yeah, go ahead.

[James]

There's another girl who kept talking about alien abductions, so that was really interesting.

[Kat Dennings]

Was that a turn on for you? I'm curious. Like, it sounds like you're just meeting people to meet weird people. Are you actually looking for something in this?

[James]

You know, I don't really know what I'm looking for, to be honest. It's just. It's proven to be a great way to meet people, really respond. Interestingly.

[Unknown]

Maybe you're looking for a girl who wears a green romper to a coffee shop and has bright red hair, tells you to sit down for the interview right away when you ask, oh, yeah.

[James]

Thank God you told me what she was wearing, because that. Now I know who you're talking about.

[Kat Dennings]

Okay, wait, other women ask you to sit down for the interview, too? How else would he find out? The aliens? That's a good point.

[Justine]

But.

[Unknown]

So now you were. Remember Justine?

[James]

Yeah, yeah, I remember Justine.

[Unknown]

What did you think?

[James]

Yeah, here's the thing. I do this a good amount, and it's just, you know, it's all over the place, the. The reactions that I get. But Justine's was like. She was really quick with it and she was. Yeah, she was different. I'll be honest, that kind of freaked me out.

[Kat Dennings]

Oh, it did.

[James]

I didn't know how to respond.

[Kat Dennings]

Because she beat you at your own game, essentially, right?

[James]

Yeah, yeah, pretty much.

[Kat Dennings]

But what does that mean? That seems like it'd be a turn on.

[Unknown]

No, Men don't like to be outsmarted.

I was Just gonna.

[Kat Dennings]

How do they ever meet anyone?

[Unknown]

James, how did. How did you feel talking to Justine like that? Were you scared of her?

[James]

You know? Yeah. Honestly, I just. I never take this thing seriously. It's just. It's just sort of a gimmick. And she. For the first time, I felt like, wow, this really could be something.

[Kat Dennings]

What? You can't let your own insecurities stand in the way of that. You want someone who challenges you, who makes you. Yeah.

[Unknown]

What's your hold up then?

[James]

I guess I'm just not used to that. I've never, never had that happen or.

[Unknown]

So you finally found her and you're.

Like, what do I do?

[Kat Dennings]

That's why you're single, my man.

[Unknown]

Like, you don't know how to move forward now that you realize you actually like her.

[James]

Kind of like she might, like, you might just be quicker than me. I don't know.

[Kat Dennings]

I think she is.

[Unknown]

Yeah.

[James]

Yeah. That's terrifying.

[Kat Dennings]

No, I mean, I appreciate the honesty.

[Unknown]

You know what's good? If you think that's terrifying, just wait till you hear that she's actually been listening to this conference conversation the entire time. It is on the other line right now.

[James]

Are you serious?

[Kat Dennings]

Hey, Scary Justine, try not to scream.

[Unknown]

Hey.

[James]

Hey. Justine, come on.

[Justine]

James, you were like. I thought we had, like, a banter.

[James]

We did. We did. It freaked me out. I've never had a banter before.

[Unknown]

Oh, man.

[Justine]

You have every right to be, like, confident and witty and, like, the guy that I met could, like, play ball, like, he could play chess. And I feel like you're just, like, afraid of that. But honestly, you. You kept up in the conversation. Great. Like, it was. I really enjoyed our conversation. I'm a little sad that, like, now you're, like, backing out.

[James]

I mean, I'm not backing out. I'm just sort of like, frozen. Not. Not sure what to do.

[Kat Dennings]

Okay.

[Unknown]

Okay.

[Kat Dennings]

This is positive.

[Unknown]

Now we need to dethaw you and get you back into action.

[Kat Dennings]

Why did I picture him popping him in a microwave?

[Unknown]

Well, whatever we gotta do. She liked your energy first met, so just bring that back and talk to her.

[James]

Yeah, I mean, I. I can definitely do that.

[Unknown]

More confident than that, though.

[Kat Dennings]

Yeah.

[James]

Yeah. Justine, I. I would like that. I would like if we could keep this going.

[Kat Dennings]

Wait, what?

[Unknown]

Oh, it sounds kind of timid to me.

Let's start.

[Justine]

Can you try to say it a little more assertive?

[Unknown]

Put some flare on it.

James, seriously.

[James]

All right, Justine, let's do this.

[Unknown]

All right, let's do this.

[Kat Dennings]

I'm not sure. I mean, I Thought you guys were gonna talk right now.

[Justine]

I thought.

[James]

Oh, no, not in front of you, dude.

[Kat Dennings]

You can't ask for interviews. You can't apply to be people's boyfriends and then not.

[Unknown]

It's like you put Riz on your application, but you have no Riz.

Yeah, show it to us.

[Justine]

Here's the thing. I think you do have Riz. I think you're just afraid of messing up, and it keeps you from being bold. Like, you did really well. You got in your head.

[James]

I think so. When there are no stakes, it's easy. But now that there's stakes, it's different.

[Kat Dennings]

Oh, that's actually kind of.

[Unknown]

Well, it is true there will be stakes if we pay for offer them, because we will offer to send you to a steakhouse.

[Kat Dennings]

Really?

[James]

Yeah.

[Kat Dennings]

Our gift cards cover them.

[Justine]

I like free things.

[Unknown]

And it's going to be an Applebee's steak.

[Kat Dennings]

I thought we were going to Sizzlers.

[Unknown]

But we'd like to send you guys out on one more date that we would pay for. If you're not too afraid. James.

Come on, James.

[James]

Yeah, I would love that.

[Unknown]

I feel like if we didn't call and push you into this, then this date never even would have happened.

[James]

Yeah, I mean, we don't know that.

[Justine]

Well, I feel like we kind of know that.

[Kat Dennings]

Okay.

[Unknown]

Justine, you're still okay with it?

[Justine]

I am open to a second interview, but he honestly sounds like, pretty different, a lot more timid. So we'll just have to see how a less rehearsed interview goes.

[Kat Dennings]

Okay. Was the first one just a show, or is it really who he is?

[Unknown]

Yeah, find out.

Let's put in a real world experience.

I'm doing the dating math on this, just like Justine did. Originally.

Originally.

And I'm saying this relationship's probably at a 5% chance right now, higher than.

[Kat Dennings]

I was gonna give it, so. Yeah, that's good.

[Unknown]

Unless he says something really smooth right.

[James]

Now, I got nothing.

[Unknown]

Okay. It's a 2% chance. Good luck, you guys.

[Kat Dennings]

Yeah.

[Unknown]

It's broken. Jeffrey in the morning.

Brooke and Jeffrey in the morning.

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[Unknown]

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[Tim Allen]

Right this way.

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[Ryan Seacrest]

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Seacrest for Albertsons and Safeway. This new year, make sure you take some time to take care of yourself and your family. Stock up on your favorite Items now through January 28th and earn four times the points to use towards discounts on groceries or fuel. Shop in store online or in the app for items like Pantene Shampoo, Old Spice Body Wash, Campers, Swaddlers, diapers, Venus Razors and Crest Complete toothpaste and earn four times points on your purchase offer ends January 28th. Visit albertsons or safeway.com for more details.

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