252: Little Boy Hands & My Dirtbag Wife (with Kal Penn)

Summary

WE’RE HERE TO HELP – EPISODE 252
“Little Boy Hands & My Dirtbag Wife” (with Kal Penn)
January 21, 2026

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Episode Overview

In this characteristically rollicking episode of "We're Here to Help," co-hosts Jake Johnson and Gareth Reynolds are joined by actor, comedian, and one-time White House staffer Kal Penn. The trio delivers their comedic brand of “advice” to listeners’ calls ranging from office fashion dilemmas to marital mystery, all the while chatting about Kal’s unique career path, cultural representation in Hollywood, and the art of podcasting. The tone is breezy, irreverent, and supportive—a blend of genuine advice and deadpan ribbing.

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Key Discussion Points & Insights

1. Kal Penn’s Career: Acting to the White House and Podcasting

[00:53 – 12:38]

• Kal recounts his unexpected detour from playing a stoner in "Harold & Kumar" to working in the Obama administration.
  • "If the only thing you know about me is that I played a stoner three times…what business does he have working for any president of the United States? And my response is always like, well, that's the American dream, baby." —Kal Penn, [01:24]
• He explains how the 2007-08 Writers Strike and an invite from Olivia Wilde lured him into politics—specifically mentioning the open bar as the clincher.
  • "She, like, casually was like, I mean, it’s an open bar. I was like, oh, I’m there." —Kal Penn, [02:33]
• Kal talks about going to grad school for international security during acting hiatuses:
  • “Going to grad school is the equivalent of…when you see actors who come into work hungover. My first reaction is, bro, are you working so consistently…that you had to get drunk last night?” —Kal Penn, [03:06]
• Discussion shifts to the cultural impact of “Harold & Kumar” and shifting media landscapes:
  • Kal describes how skeptical Hollywood was about two Asian-American leads, the lack of initial marketing, and the film’s later cult success via DVD.
  • “You’re assuming white audiences can’t laugh if somebody doesn’t look like them, which is like, so demeaning…Turns out, people just want to laugh.” —Kal Penn, [05:59]
  • The hosts note how “democratized” new media like podcasts and streaming have become.
  • “If the audience likes something, therefore, it wins. It is not about marketing...It’s a democracy.” —Jake Johnson, [07:43]

2. Kal’s New Podcasts

[08:46 – 12:46]

• Kal speaks about two new podcasts:
  • With Ed Helms: A limited run podcast about audiobooks and the booming culture around them.
    • “I didn’t realize how huge the Audible audiobook space is…people will listen to podcasts that dissect the audiobook.” —Kal Penn, [09:09]
  • Here We Go Again: An optimistic look at pop culture and politics through history and expert interviews.
    • “Everything is like, doom generation, the world sucks…But I felt like I don’t have those touchpoints anymore of learning from somebody…here’s how something was 50 years ago, and here’s where I actually think it’s going.” —Kal Penn, [09:29]
    • Example: A playful deep dive with Bill Nye about the evolution of the space race, and a chat with Pete Buttigieg about airport logistics (“Why are there never gates ready when you land early?”).
      • “Of course they knew you were coming. That’s literally how the technology works.” —Kal Penn, [11:33]
      • Buttigieg real answer: “They knew you were coming early. They just didn’t want to pay another person (to get you to the gate).” [12:04]

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CALLER #1: Sarah’s “Tiny Tie” Dilemma at the Iowa Law Firm

[18:21 – 43:41]

Situation

• Sarah, the youngest—and only female—attorney at a small Iowa law firm, needs advice about a colleague, “Connor.” He wears the same, comically short (kid-sized) tie to every formal event, including court.
  • “It lands inches above his belly button. It’s almost clownish… even wore it at his father’s wake.” —Sarah, [22:03]

Debate & Pitches (peak absurd advice and genuine problem-solving)

• Kal’s Approaches:
  • Questions if Connor has tiny hands for practical reasons, then asks if the tie might have sentimental value (e.g., was it from his late father?).
    • “Does he have tiny hands?” —Kal Penn, [24:43]
    • Suggests, “Either buy him one tie or buy him 10 children’s ties.” —Kal Penn, [28:54] (quickly shot down for potential cruelty)
• Jake & Gareth’s Strategies:
  • Gift him a new tie (or a set) as a group holiday present, possibly pre-tied in case he doesn’t know how to tie one.
  • Get all partners involved to make it less personal—everyone receives a tie in a matching color, possibly with initials embroidered.
    • “This is a great gift to give everybody: a beautiful full-sized tie with their initials on the back.” —Jake Johnson, [32:10]
  • Create thematic office events or photos that require everyone to wear their new ties.
  • Use positive reinforcement and playful compliments to encourage wearing it:
    • "Whoa, that tie looks so good… You look hot—watch out, ladies of Des Moines." —Jake Johnson (suggesting what Sarah could say), [36:14]
  • If he still refuses, spill grape juice (or coffee) “accidentally” on his old tie and replace it with the new one—a back-up option for desperate times.

Role Playing:

• Sarah practices gifting the tie and delivering compliments in mock exchanges with Kal as “Connor,” growing more comfortable each time.

Resolution

• Sarah decides to gift everyone in the office pre-tied, personalized ties for New Year’s, using positive attention and peer pressure (group photos, matching attire) to encourage the switch. Backup plan: grape juice.

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CALLER #2: Jim and the Mystery of the Missing Ring (“My Dirtbag Wife”)

[48:08 – 65:24]

Situation

• Jim from Chicago’s western suburbs notices his wife is no longer wearing the sentimental ring he designed—a gift featuring their children’s birthstones and an inscription. Fears she lost it but doesn’t want to make her feel bad.
  • “We’re not afraid of confrontation, so she would have mentioned something if she wasn’t feeling bad about it.” —Jim, [50:55]

Brainstormed Solutions

• Gareth’s "Sweetheart" Approach:
  • Organically discover the issue via photos; frame a photo for her as a gift and point out the ring “organically.”
    • “In that moment, you can make the connection: 'Hey, where’s that ring?' and set it up like an organic gotcha.” —Gareth Reynolds, [54:07]
• Jake’s “Chicago Guy” Tactics:
  • Absurd suggestion: Stage a “theft” story to unite in the search for the ring, or have a cop buddy call and ask about missing valuables.
  • More practical: Involve a brother-in-law (her brother) to innocently ask to see the ring because he wants something similar for his girlfriend.
    • “Can I see that ring that Jimmy got you? I want to get something similar.” —Jake Johnson, [61:05]
• Kal’s Insight:
  • Highlights the opportunity for kindness—if she lost it, maybe a chance to design a new keepsake together.
  • Supports letting the brother-in-law approach play out for minimal awkwardness.
    • “If you don’t feel comfortable asking directly…this is the next best thing.” —Kal Penn, [64:04]

Memorable Quote

• “You also said on this call that means the world to me…you referred to her lovingly as, I believe, a ‘dirtbag’...that’s a term of affection and it doesn’t translate.” —Jake Johnson, [63:22]
• "My dirtbag wife likes [Malört]..." —Jim, [62:37]

Caller's Plan

• Jim decides to get the brother-in-law to ask about the ring during upcoming holiday gatherings and report back.
  • “I don’t think he’ll rat me out—he gets it.” —Jim, [63:00]

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Notable Quotes & Moments

Kal Penn on representation:

• "You're assuming white audiences can't laugh if somebody doesn't look like them, which is, like, so demeaning, frankly..." —[05:59]

On podcasting and new media democracy:

• "If the audience likes something, therefore, it wins...it's a democracy." —Jake Johnson, [07:43]

Gareth roleplaying Sarah's approach to 'Connor's tie'

• “Let me see it on you. I don’t think that’s crazy. People want to see you happy to have it.”—Gareth Reynolds, [38:42]

Jake, imagining the tough conversation:

• "Hey, Jesse. Jesus Christ. I got a pickle I want to talk to you about, babe." —Jake Johnson, [55:34]

Jim, affectionately:

• “You know what? Actually, my dirtbag wife likes that stuff.” (re: Malört) —Jim, [62:37]

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Important Segment Timestamps

• Kal Penn introduction and career chat: [00:53 – 12:46]
• Kal’s podcast discussion: [08:46 – 12:46]
• Caller 1 (“Tiny Tie”): [18:21 – 43:41]
• Caller 2 (“Missing Ring”): [48:08 – 65:24]

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Episode Tone & Takeaways

The episode blends genuine warmth, comedic exaggeration, and real (if sometimes ridiculous) advice. Kal Penn’s presence adds thoughtful commentary on diversity, media, and optimism. The advice portions are as much about commiserating in life’s weird moments as about literal “solutions,” with plenty of running bits, group brainstorms, and hilarious digressions.

For those who haven’t listened:
Expect big laughs, pragmatic wisdom, and a lot of heart—especially if you've ever had to delicately ask a coworker to update their wardrobe, or wondered how to handle a spouse’s quietly missing jewelry.

Transcript

[A]

New year, same extra value meals at McDonald's.

[B]

So now get two snack wraps, plus.

[C]

Fries and a medium soft drink for.

[B]

Just $8 for a limited time only. Prices and participation may vary. Prices may be higher in Hawaii, Alaska and California. And for delivery.

[A]

This is a Headgum podcast. And we are back. We got a guest today. The Great Cow Pen is joining us.

[B]

Hey, thanks for having me, guys.

[A]

Thank you, man. You know, Cal, you've had a really interesting career, man. Gareth and I both did Harold and Kumar together.

[B]

Yep.

[A]

We were all in that guy together. You popped big on that. And then you got into politics briefly.

[B]

Yes. For, like, two years.

[A]

But you didn't go casually. I remember being like, because I've always known you as an actor. You know, I've known of you. I've been a fan for a long time, so I was always watching your work. Then you were, like, hanging out with Obama.

[B]

It was. Yeah. I mean, I think if the only thing I have to explain this to audiences sometimes, like, if the only thing you know about me is that I played a stoner three times. And then you're like, this guy, what business does he have working for any. Any president of the United States? Like, forget politics. Just the. The act of doing that. And my response is always like, well, that's the American dream, baby.

[A]

Yeah, but also from the outside, you did do the American Dr. Also in.

[D]

The Second Herald in Kumar. It's loosely around the government. So maybe that was where you got the bit by the butt.

[B]

Maybe. I mean, I had no intention of actually going and working in government. It was a very different time. It was like 2007, 2008, and we were all on strike because the screenwriters were on strike. And I remember Olivia Wilde, who is a wonderful actor, director, invited me. She was like, there's an Obama event. And at that point, he was like a junior senator from Illinois. Nobody knew how to pronounce his name. There were 12 people running for president. She's like, do you want to come to this event? I was like, absolutely not. There's nothing I would rather do less than go to a political event in Los Angeles. And the third time she asked me, she, like, casually was like, I mean, it's an open bar. I was like, oh, I'm there.

[D]

It's great.

[B]

You should have led with free drinks.

[D]

Changes everything.

[B]

Totally changes everything. And then kind of one thing led to another. I ended up volunteering for the Obama campaign for a while, and then that turned into like a year and a half of kind of working on things. Like, arts policy. And I was going to grad school at the time for international security, which is not a thing that I had, like, advertised publicly.

[A]

You had been a working actor and then decided in between gigs to go back to grad school.

[B]

Yeah, there was a program that you could do, like, half of it as a distance student online. So I would do it, like, you know, if I was working on a season of House, for example, I would do it during hiatus or I would, you know, between movies. You'd have, like. I mean, you know, this. Actors are. To me, it's like going to grad school is the equivalent of like. Like, you know, like, when you see actors who come into work hungover. And my first reaction is, bro, are you working so consistently throughout the year that you had to get drunk last night?

[A]

By the way, you're 100% right.

[B]

Like, I'm envious of that. I've never had that type of career.

[A]

You worked 14 days in 2024. You did not need to get drunk last night.

[B]

I can get drunk most Tuesdays.

[A]

Yes, you. That's a thing. I can.

[D]

I do.

[A]

And then what was the Herald and Kumar experience? Because that movie, really. I don't think people nowadays realize how big that movie was when it came out.

[B]

Yeah.

[A]

And how nowadays everything does feel different. I say that as an old white guy, but you just see so many different people of color and everything on screen now with streaming, it's not odd to me to be like, oh, I'm now watching a show with people in the main cast that never would have been. It was wild when you two guys were the leads.

[B]

Yeah.

[A]

Of a studio comedy. And I was, like, great. And that. Crushed. And that nobody was talking about the fact that it was you two guys. They were just like, oh, yeah. That funny stoner movie.

[B]

Totally. That's what felt good about it. I remember when we made it, you know, I couldn't believe they were making a movie like that. In fact, John Hurwitz, who's one of the. One of the writers and creators of Harold Nick Moore, I ran into him at a. At a mutual friend's party before he had cast, before he'd sold the movie. And he sent me a script, and I was like, this is the funniest thing I've ever read. You're never gonna sell it in Hollywood. Because that was my experience up until that time. Right. Like. Like, no Shade to Van Wilder. I had a great on it, but I'm literally playing a guy named Taj Mahal. Like, he's named after A building.

[A]

Wow.

[D]

That is an era.

[A]

Not even name that really funny thing.

[B]

So. And again, not complaining about it. Just, let's set the tone of the.

[A]

Time, Live in reality. This is reality, right?

[B]

No, that was the reality. So. So I said to her, it's like that there's no way you're selling a movie where these two guys are just dudes. Like, I've. I've been playing, like, granted, it was one of the seven wonders of the World, but it's still a building. Right? And then he, of course, sells it. And Hurwitz says to me, I'm sorry, that was your experience, but we are making Harold and Kamar go to White Castle. We're not making a movie called David and Jason go to McDonald's. Yeah. So I was like, oh, I like this line. I like this guy. But when it came out, dude, there was buzz during the casting process that said, we don't know if Hollywood's ready for a movie with two guys who look like me and John Cho. And my takeaway from that was, you guys are underestimating the audience.

[A]

Yeah. That's cool.

[B]

You're assuming white audiences can't laugh if somebody doesn't look like them, which is, like, so demeaning, frankly, and degrading to. To an audience. Right. And I was like, that's. I love comedy. Everybody loves comedy. The movie comes out, and it does really poorly in the box office. So those first two weeks, it tanked. And so I was getting phone calls that were like, see, we told you.

[A]

America's not ready, and you're trying to spin it. You're like, I've always been saying that. Yeah.

[B]

That's why I'm doing Van Wilder, too, you guys.

[A]

I'm speaking right now for Taj Mahal Sen. And I'm excited about it. Yeah.

[B]

But to your point, guys, the movie drops with no marketing on dvd, and fans found it on their own. It explodes, and it explodes in Arkansas and Nebraska and Tennessee, not just the coasts. And it was so reassuring where I was like, number one, I'm very glad, just selfishly, that people are enjoying this movie. And number two, like. Like, screw you old guys who underestimate the audience. Like, people just want to laugh, you know, and.

[D]

Yeah, it helps a lot.

[E]

Yeah.

[A]

But I will say in. In terms of that and in truth. And one of the things. And I want to talk to you about your podcast, too. The why I'm loving this space.

[B]

Yeah.

[A]

Is similar to that and how you couldn't do it in the theaters, because all that is marketing machines. And you can feel what movies these studios want to win awards and the agenda that Hollywood wants and what they want to win. And, you know, they're going to put enough money in that it's going to happen. Yeah. But what I love about what DVDs did, what rentals first did, what cable did, and now what, like, what podcasts are doing is it's a democracy.

[B]

Totally. Yeah.

[A]

If the audience likes something, therefore, it wins. It is not about marketing. It is not about pr. It is not about a push. It's not the big studio machine goes, we're gonna make a star of this kid.

[D]

Yeah.

[A]

It's the audience goes, that was funny with those two guys in the White Castle. Why? I don't know, but I liked it totally. And you're like, that's all it takes.

[B]

It's all it takes. And I love that not everything has to be for everybody anymore. I like, so good. I love, like, I love stand up comedy broadly, but, like, I can love a Shane Gillis and I can love a Nanette like, the same night, and they couldn't be more different. Right. And I just, I love that about.

[A]

The fact that, man, I could not agree more. And I also, I love, in doing it, that now even the executives are getting it and they're giving a different style of note where they'll go, like, you guys know what you're doing. And you're like, you didn't say that before you asked. I was like, I'm glad you are. Now you and Ed Helms are doing a pod Ralph.

[B]

We are. So I'm doing two right now. There's one with Ed. They're both with Ed's company. Snafu. The one I'm doing with Ed is about audiobooks. So it's a short six episodes for the season. And it's. I didn't realize how huge the Audible audiobook space is and how people will not just listen to audiobooks, but then want to listen to podcasts that, like, dissect the audiobook.

[A]

No. So it's massive.

[B]

It's massive. And it's so. It's like the nerdy side of me that I just think it's so interesting. Like, really. We had. There was a book about Mark Ronson that was one of the ones we covered. And I got to talk to Questlove for, like, an hour and a half.

[A]

That's cool.

[B]

Just about, like, music and marketing and that whole life and that whole world.

[A]

That's cool.

[B]

The bigger one I'm doing, it's Called Here We Go Again. And it's basically a look at pop culture history and things that happen in politics, although it's not a political podcast with the past, present, and future. And basically what I wanted to do with that is every time I was scrolling through things, everything is like, doom generation. The world sucks. Why would you pay attention? It's just everything's negative. And I felt like I don't have those touch points anymore of learning from somebody who is maybe a little bit older than me or more experienced or an expert in something. It was like, hey, here's how something was 50 years ago, and here's where I actually think it's going outside of this crazy next 12 hours where everyone's going psycho over a news story. So, for example, we had, like, the first episode was Bill Nye. Everybody loves Bill Nye. And I basically get to talk to Bill Nye about the space race. And in the 1980s, the space race. I'm a big astronomy nerd. The space race was between the US and the Soviet Union because of the Cold War. And now the space race is between, like, five billionaires, basically. Yeah, totally. So, like, what changed? When did we go from it being publicly funded to, like, private sector push? But some of that, by the way, NASA was. It was like, by design, where they wanted to spin stuff off to be privately viable. So, like, just super interesting things that I didn't know. I'll give you an example of one of the political ones I had Pete Buttigieg, former transportation secretary, was on, and I did not want to talk to him about politics because there are great political podcasts out there, and I'm just not the yelling and screaming guy at all. I would rather make dick jokes with a political person. So I was like, okay, so I have. I have the former transportation secretary on. I'll ask him serious things about infrastructure that sound boring when you use words like infrastructure. But really, my pet peeve is on the rare occasion that your plane lands early, how come the captain is like, well, folks, we're a half hour early, and unfortunately, there's no gate ready for us because they didn't know we were coming, so we're just gonna hang. Of course they knew you were coming. That's literally how the technology works.

[D]

It drives me crazy.

[B]

It's how it worked. That's the one thing they knew is exactly where you were and precisely what time you were coming. Yeah, you can make up any excuse but, like, why? Why is that what they think we're stupid enough to believe? And so you know, Buttigieg was like, is that your. Is that really the question? I was like, yes, dude. I need to know the answer to this. Is there an answer?

[A]

He's like, well, it's true. Podcasts are stupid.

[B]

He did answer the question.

[A]

What'd he say?

[B]

Apparently, it has to do with sched and the types of gates there are. So, like, usually there are. Let's say an Airport has 50 gates, but they're only using 25 of them. There are 25 ramp operators who know how to use the gate, and those specific gates are built to accommodate specific types, types of aircraft. So they knew you were coming early. They just didn't want to pay another person.

[A]

Right.

[B]

To get you.

[A]

That's hilarious, by the way.

[D]

There it is.

[A]

But I also don't want to hear the pilots say that. I don't want them to go. Please, everybody, hang out. We wanted to save a little bit of money, so just stay in your seats.

[D]

Oh, that's a good point.

[A]

How enraged I would be. So, wait, Natalie, are they here?

[F]

Yeah.

[A]

Okay. Cal. What? So what is the name of the new podcast?

[B]

Thank you. The podcast is called Here We Go Again. It's light, funny. Hopefully you end each episode feeling a little bit better about the world, and you can listen wherever you get your podcasts.

[A]

I love it, brother. Thank you for joining the show. Let's take some calls. This episode of We're Here to Help is brought to you by Walden University. For over 50 years, Walden University has helped working adults turn ambition into action through flexible distance learning. Today, our mission is simple. Provide access to education for professionals ready to level up and create real change.

[E]

You know, Jake, you and I are big believers in evolving, always getting better, always improving. You don't want to run in place. You want to jog forward, friends. So, I mean, this is a great way to educate yourself, get smarter, get better, get more professional at whatever your given vocation is.

[A]

Walden is where students get the w, those big and small wins that help them move forward and create the change they want to see in their lives, careers, and communities. With graduate degrees in nursing, social work, counseling, and psychology, as well as undergraduate and certificate programs, Walden empowers students with the skills and the confidence to get it done.

[E]

I'm a classes guy. I have taken so many classes in my adult life because I feel like your real education starts after the forced education.

[A]

So, like, I kind of agree.

[E]

Yeah, you know, it's like, always be getting better, always learning new things. I'm a huge, huge supporter of this.

[A]

With Walden's Tempo learning you're in control. No set weekly deadlines, no rigid schedules. Just the flexibility to progress toward your degree at your own pace. That works for me.

[E]

Me too. Me too.

[A]

What if we both went to Walden University and got a degree?

[E]

Oh, my God. Jake. Reliving the college life together and did.

[A]

It like a Rodney Dangerfield movie where he went back to college. Walden University set a course for change. Certified to operate by Chevrolet. This episode of We're Here to Help is brought to you by 1-800-Flowers. Isn't that right, Stephen Berg, host of Weird Here to Hell?

[E]

Oh, it sure is. Correct. Correctamundo, Jaco. I'll tell you what. My lovely wife, she always, I feel, deserves something that shows that I put thought and effort into the situation. Right? It's why I trust 1-800-flowers.com Jake. They have never let me down. Amazing bouquets, high quality, delivered on time. Which is something because today a lot of things aren't delivered on time. And they do it every single time.

[A]

You know who I send my flowers to? Not my lovely wife.

[E]

Who?

[A]

Pam Reynolds.

[E]

Oh, well, I'm, you know, I'm with you.

[A]

I have sent a.

[E]

Probably a baker's dozen bouquets to her and it's paying off because she likes me the most.

[A]

No, she doesn't. She likes me the most.

[E]

Contrera, mon frere.

[B]

She is quite the Berg fan.

[E]

I mean, she has a calendar. Do you have a calendar, Jake? I don't think you do.

[A]

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[D]

I have so much stuff from Quint's. I've got my corduroy jacket. I've got a wool coat from Quint that is the best coat. It's my number one coat when I go on the road and I'm in colder climates. Keeps you warm. Can't recommend it enough. So refresh your winter wardrobe with quints. Go to quint.com heretohelp for free shipping on your order and 365 day returns. Now available in Canada too. That's Q U I n c e.com here to help. Free shipping and 365 day returns. Quint.com here to help.

[B]

Hello.

[F]

Hi.

[D]

Hi. Welcome to the show. Can we get your name, please?

[F]

Yes, my name. You can call me Sarah.

[D]

All right. Hi, Sarah. Sarah. Where are you calling from?

[A]

Him?

[F]

I am calling from Iowa.

[D]

Iowa.

[B]

Beautiful.

[A]

What part of Iowa is there? Here we go.

[F]

I don't want to be more specific.

[A]

For I just lived in Iowa. I just lived in Iowa City for a while. We know.

[D]

We've heard it. We've heard it. Look, Sarah, we're going to get it. Sarah. Sarah, we've got to cut Jake off, which is what the bar said in Iowa. We've got Jake, you've got me. We have a great guest who's going to help you out today. We have the fantastic Cal Pen is joining us today.

[B]

How are you, Sarah? Good to meet you.

[F]

You. Oh, my gosh. Good to meet you.

[D]

Yeah. So step it up, Sarah, wherever the hell you are.

[F]

Okay. Yep, got it.

[D]

Lock in. So what's going on, Sarah? What can we help you with?

[F]

Okay, so I am an attorney at a small firm. I will tell you. We're in like one of the bigger cities in Iowa, but a pretty small firm there. Seven of U.S. attorneys.

[B]

Jake.

[D]

I. I think she's trying to be general. It's not.

[F]

Can neither. Can neither confirm nor deny.

[D]

I will say it sounds like you're confirming, but go ahead.

[B]

She's actually in Nebraska.

[F]

I'll tell you this.

[C]

Yeah, Jake.

[F]

It would never be Ames.

[A]

Then it's Des Moines.

[D]

Wow.

[A]

Okay. You're an attorney at a small firm.

[D]

Seven attorneys. You're in Des Moines.

[F]

Yep. I'm the youngest attorney, but I'm also the only female attorney at the firm, which honestly works out great for me. Like, they're. They're all the other attorneys are all male, between maybe like 40 to 60 ish. All of there are five partners. So five of them are partners, but then there's me. And then there's one other non partner co worker. He's maybe 40 years old. We can call him Connor. And Connor is. He's a great guy, like super lovable, hilarious. He is single, single, single. Never been in a relationship for the entire time that I've known him. And I think for like as long as he's worked firm, he, you know, has no kids or anything like that.

[A]

And.

[F]

But he does seem, but he is a little bit awkward, but he seems self aware about that in a way that's kind of surprising. Like, he seems like he makes jokes about it sometimes. But the main issue is he seems to own one tie. Like one single tie, which is normally a problem. Yeah, you don't like, you don't. I don't know, maybe you don't need more than one tie. I don't know. But he owns one. And the problem with this tie is not the pattern. Pattern's fine. It's that I'm pretty sure it's an adolescent size tie, like length.

[D]

Oh, my God.

[A]

That's a cruel.

[F]

I will admit that I'm out of my depth here. Like, do they make different size?

[A]

Presumably they make different sizes, right?

[D]

Yeah. Look at Trump's tie stand to his knees.

[A]

He's got a little boy's tie.

[B]

Fair enough.

[F]

Yes, that's right. Well, this is like way worse than Trump's tie. This tie is. Right, right, right. It's so short. It's like almost clownish. I mean, we're talking like, it comes. It comes inches. It lands inches above his belly button.

[D]

Oh, my God. Okay.

[B]

Crazy stylistic choice, I'm gathering.

[A]

You never know.

[F]

Could be he has kind of a beer belly. And so the tie, just like the end of the tie Just kind of rests there. So it's like. It's worse. It's drawing attention to it. Right. And so here's the thing. So we are like the Midwest, the legal profession, the Midwest, at least in Iowa, is fairly casual. Like, we don't wear suits every day. Most of the days at the office is pretty casual. But, you know, when we have to wear nice things, we have, we're in front of, like, a judge or something. You know, we're doing a deposition or we're appearing in court or something like that, where it does kind of matter. And so every time he has one of those more serious things, he whiffs out this. Am I allowed to swear on this podcast?

[A]

Yes.

[D]

Okay.

[F]

He whips out the same fucking tiny ass tie. And so one. Here's the other thing is, I know that it's not just happening in, like, the professional context, because a few years ago, his dad passed away and some of us went to the wake. And sure enough, Connor is at his own father's wake in this tiny child's tie.

[A]

Hey, Sarah, you know, like, about how you've done this setup, You've switched it to a setup into, we're all having brunch gossiping. It started off as a setup of a podcast, and now I feel like I want to lean in and go, like, that's insane. Yeah, we are now just brunch.

[F]

Gossip is brunch. Brunch gossip's one of my favorite things.

[A]

Well, you have turned into our friend Steve Burke, because this is the zone he just lives in.

[D]

Well, you didn't talk about food enough, but.

[A]

Yeah, I know, but this is the feeling. It's like. Okay, so what is this guy's name, though? Did I miss.

[E]

We'll call him.

[F]

We'll call him Connor. Okay, so that's not his real name.

[A]

But that's so Connor. Single, no kids. He's awkward. He's got one tie. It's a boy tie. Inches above his little belly. He wears it all front of a judge. He's.

[F]

He.

[A]

It's not professional, but he also wears it at home to, like, if he's got to do something, like, awake, which is a nightmare. So, Sarah, what is the specific question we could help you with today?

[F]

How do I get him to stop wearing the tiny tie? Wear an appropriately length pie without embarrassing him.

[A]

I mean, I got the easiest pitch in the world, unless anyone wants to go. Somebody. Somebody go first, because I got an easy one. Gareth, you got anything? Cal?

[D]

I got an easy one, too. I mean, I got an Easy. And a hard. Cal, you were going to jump in.

[B]

Yeah, I. Well, I have a question and then a suggestion. Sure. Question. Does he have tiny hands?

[A]

No.

[F]

I am a happily married woman, Cal, so I haven't looked at his hands.

[B]

Sure.

[D]

I would just be. What.

[A]

What's that? What. What's happening? Normal question, Sarah. Weird response.

[D]

Crazy answer. Your husband's got hand envy.

[A]

I don't think he's talking about, does he have a big dick? He's talking about, does he like to tie the tie because it's little. It's easier to manage.

[B]

I'm imagining if he's got tiny, tiny hands that he.

[D]

Rex needs a. Yeah, he doesn't want.

[A]

To deal with all that fabric. You pervert. Sarah.

[D]

Yeah?

[A]

Check it out.

[E]

Hands.

[D]

Honey, you're drunk.

[B]

And then the second question is, do you think he's hung? No, it's just. It's just a question about the tiny hands related to the tie.

[A]

But.

[B]

But the, the real suggestion, the thing that, like, I think before moving forward, I like, you need to know why. What's the deal with that tie? Like, did his. Did his late dad gift him that?

[A]

No. I would. I would not say this has anything to do with deeperness. Besides, he's got bad fashion. Well, ties aren't like underpants in that. You don't have to change them. You can. I don't remember the last time I've washed a tie. If I. I don't think.

[D]

I literally don't know if you can wash it.

[A]

Right. Like, I think you, You. You go. You wash your suit if you're gonna get it, you know, dry cleaned.

[B]

Yeah.

[A]

The tie just goes up. So you go like, you got one tie that works. He's single. There's no partner in his life going like, so, Connor, what do you think about looking a little bit better? He goes like, there's no sex in my life. A tie is just when I need to wear it. I got one.

[D]

It. It's. It's also. It is a problem. It's tough because I do think you're right. It's a really weird thing to bring up, but I cannot imagine a guy looking like Chris Farley in front of a judge and feel about slam dunking a case like that. I think your first pitch is probably what I have, which is. It's the holiday season.

[A]

Exactly. Right.

[D]

I mean, what a time to just.

[A]

Give him a die. We give him 12 ties.

[D]

Yeah.

[C]

Long.

[D]

Yeah.

[A]

Yeah. We give them men's ties that are normal size.

[B]

Yeah.

[A]

Okay.

[F]

That was so, so my Husband and I have been brainstorming about this for quite some time. That was one of the ideas. But the thing, I have a concern and no evidence for this, but I'm concerned that he doesn't know how to tie a tie like he tied this one in 2010.

[A]

You give then, you know, then pre. Tie the ties, give them 12 free tied, normal sized ties.

[D]

Or you could give him some ties and let him bring up this issue when you're not, when he's not wearing it. We could solve, solved that.

[A]

Go ahead, go. I'll go, actually.

[D]

Okay.

[A]

We create a fake charity that you ask all the lawyers there to donate a tie because you are, it's like a fun thing you're sending, it's called like the tie giveaway. And you're sending ties to this organization because he only has the one tie. You say it's a tie off your back day. So whatever tie they're wearing, I mean.

[D]

But Jake, very quickly, I hear you, but imagine if you're not a partner at a law firm and you're walking around to people above you where you want to be a partner someday and you're going, hey, guys, it's me, Sarah. Hey, love it here. Can I get everyone's tie?

[F]

But okay, let me, let me add one factor that maybe we'll, we'll factor into your pitches. So the, the partners know and we talk about, I've gone to them and been like, guys, what the fuck are.

[B]

We going to do?

[A]

So Sarah, this is, but then they don't do anything. That's okay. Sarah.

[B]

I think you get a new tie.

[A]

Yeah. So what's your thing? You just say buy him a tie.

[B]

Buy him a tie. But either buy him one tie or buy him 10 children's ties.

[A]

Let's not do the 10 children even.

[D]

Like, not it like he's breaking out of jail, just slowly down.

[E]

Yeah.

[B]

The same type of tie that he has, the same size, just a different.

[D]

I, I, I, Okay, I got one. And I, I look, the fact that the partners know, I think does open us up to a different world of pitches because, you know, there's, there are options where we could float an email out there. We could scapegoat another one of the partners. Come on, guy. Change your tie every once in a while. We could do that, but why not? Does he drink coffee?

[A]

Does he?

[F]

That's a great question. I don't know that I've noticed. If he does, he definitely drinks Diet Mountain Dews. If that totally works.

[E]

Boy.

[D]

Okay, we really. This man is Honestly, he's like.

[F]

He's a gamer.

[D]

Here's my.

[C]

He's a big video gamer.

[D]

This is crazy. I do not want this guy representing me.

[A]

Sarah, we all knew that before you said it. Yeah, well, there's some gag giveaways getting.

[D]

Tougher, but my pitch would be this. You get him a coffee, you get the lid and you take a pin and you poke a couple holes in the top of the coffee so that we're pre poking a spill on the tie. And at that point you can go, oh my God, I've ruined your tie. And that's where you come in with the Maya Culpa tie two days later.

[A]

I had written something similar, Gareth. I had written grape juice. I think yours is smoothie smoother. But I would do the spell. Wow, she does so do the Harlem Globetrotter, then feel so bad and then the next day gift him a new tie and go, I am so sorry.

[D]

Don't hate that either, to be honest. But I mean, we are putting a lot on you, Sarah. Go ahead, Kel.

[B]

I think you can just gift him a tie without reason. And if you need a reason, then just get six other gifts for the other people you work with.

[D]

With. How about if they're ties? How about if you get everyone you work with a tie?

[B]

Yeah, it's all about.

[D]

Anyway, so you're.

[A]

So you're company tie.

[D]

You're giving everyone a tie. You could do similar. You could do picks and you could even tell the partners, hey, in the new year, I'm going to give everyone a tie the next day. Everyone wear the tie, please, for me. Whatever.

[A]

No, you do this, Gareth. You get everybody for Christmas, you get everybody a tie that they all kind of match and then you have your closest friend, another lawyer, go, hey, guys, let's all start wearing these ties. I think it looks good that our ties match Eve.

[D]

Okay, but let's say they don't like that. I would say just have the partners comment on how good his new tie looks so he feel like you just pre. You know, we pre bake it.

[B]

Get him a tie with a logo on it, have this custom made and the logo is a picture of him wearing his tiny tie.

[D]

Or to that point, what if we. What if we give him his initials on the tie or something like.

[B]

That's a great idea. Yeah.

[A]

If on the back you give him.

[D]

Like a little sweet his initials, it's kind of special.

[A]

Everybody gets their initial. This is.

[D]

Everybody gets their initials.

[A]

A great gift to give everybody is a beautiful full size tie with Their initials on the back.

[F]

I like that.

[D]

And you know what?

[A]

Every time he wears a little tie, go like this. Oh, did you not like my tie?

[B]

Oh, yeah.

[A]

And he'll go, I love the tie. And you go like, oh, okay. And just pretend you get your feelings hurt. And he'll go like, ah, I love my mini tie, but I gotta wear that because I don't want Sarah to get her feelings.

[D]

Grape juice.

[B]

Grape juice.

[D]

This is the other thing I'd say if the. This. If he for some reason doesn't wear that tie, I like the Jake. Like, let's foam the Runway here a little bit and get that. So the partners. We're all going to wear our ties, you know, whatever. And if he, for some reason, doesn't wear it, then you're right. He doesn't know how to tie a tie. I think at that point, you can step in, explain to him. It's very easy. It's a better look, and you'll show him how to do it. But I also think if you're trying to show the people that you work for that you're good at problem solving and evaluating situations and getting through it, I mean, the stakes are a little high here. So I think we're getting you in a good zone.

[F]

I agree. I think. I think maybe pre tying it.

[A]

Yep.

[F]

Is still the move just to remove that. That barrier.

[A]

I think you're actually dead right. But I would then have. I would re. I would pre tie all of them.

[F]

Oh, yes. Okay. A uniform pre tie situation.

[A]

And then so they all have a very similar look. And you just say, this is the gift. And it's thoughtless to everybody else. They go like, she pre tied it. But it's. There's a little method to the madness.

[D]

Initials on the back.

[F]

And then they can. They'll know why. Like, I can say why, too. I can like, hey, this isn't Because I don't think you can tie a tie.

[A]

So my question to you, Sarah, is from Des Moines. What are you gonna do?

[D]

Stop cross examining her clearly?

[A]

Des Moines, what are you gonna do?

[F]

I am going to gift everyone a tie. I'm. But you know what I'm gonna do? I'm gonna get everybody a tie and maybe only put his initials on his to make him feel extra special.

[A]

Why?

[F]

Or is that weird?

[A]

Weird. Okay, if I'm him like this, did you guys get your initials? And they all go, no, just you. And I go, why?

[D]

Yeah. And if your husband doesn't like you looking at other men's hands, I mean, Specifically, initially, one guy's eye, I would.

[A]

Go, why does mine say J.J. nobody else's? And everyone goes, I don't know. I'll go. That makes me feel uncomfortable.

[F]

Okay, good.

[A]

Everybody gets it. I'll do grape juice. I'll never think it, but if it's just me and I'm a weird single guy who games with little hands, I'm getting weirded out.

[F]

Okay.

[B]

Okay.

[F]

I think you're right.

[A]

Okay.

[F]

So I think gifting everybody a tie, and then I think if he still, like, pre tied, if he still doesn't wear it, I think I have no choice but the coffee, grape juice.

[A]

Yeah, Well, I think you're right.

[D]

Pre coffee, grape juice. I think you have every right at that point to say to him, did you not like the tie?

[A]

I think you're right. Can I at least see you? Can I see you? You know what you do then? Here's what we do. Before grape ch. Shoes, you. If you give him the tie, doesn't wear it. You one day go, hey, guys, can everybody come in on Friday wearing the tire next time we need it? I'd like to take a group photo. Then maybe once this creature habit puts it on, he'll go like, hey, look at me in a man's tie. Look at me looking not so bad. Well, you can compliment the hell out of them.

[D]

You could say that the person who made the ties, like, liked your idea for a Christmas gift and wants to see everyone wear them. You know, something like that.

[A]

Oh, you. You know what you could actually do? This is a real easy way. We forgot about the fact that he's single, no kids, awkward in games a lot. You know what he doesn't get is a lot of compliments from women.

[D]

Yeah.

[A]

I would say the day you give it to him, you say, hey, would you try it on? And it's already pre done. He puts it on and then go like, whoa. Yeah, I think that looks. And use the term sexy.

[D]

Yeah. And then cover your mouth like it.

[A]

Slipped out, but just go like that. Or go like this. Or do it playfully go like, whoa, that color. You look hot.

[D]

And then.

[A]

Oh, and go, watch out, ladies of Des Moines.

[D]

Don't tell my husband I said that. And I'm not in Des Moines.

[A]

Yeah. And then go. But for real, you look great, man. That's a. That's a good looking tie on you. Okay. Because a little bit of a tie.

[F]

Can lay it on quite that thick. But I think I can do. I think I can do some.

[A]

All right, Sarah, let's try this really fast, Cal. Do you mind being calm? Connor?

[D]

Yeah.

[A]

You just got the tie, Sarah. Let's see how you're gonna do it. Let's just get a taste of this.

[F]

Okay. So he just got the tie.

[A]

Just hand it. Well, actually walk in. Let's do the whole thing. Walk in and give him the tie. It's. It's the. Right after Christmas break.

[B]

S. Hang on. I'm playing video games. Hang on, hang on, hang on. Kill.

[D]

All right, all right.

[B]

I killed this guy.

[F]

Hey, Connor. Hey. I hope your holidays went well. I've got a bit of a late gift for you here. I gave one to everybody, but I really hope you like it.

[B]

Oh. Oh, it's a tie.

[D]

Yeah.

[F]

You know, I noticed that you have sort of the one that you wear a lot, so I figured you could use a new one to add to the rotation.

[B]

Oh, wow. Thank you. Thank you. Then I take the box and I start to put it in the drawer.

[F]

But, you know, I'm actually. This is really embarrassing, but I'm really excited about these ties. So would you be willing to. You. Would you want to try it on and just show me how it looks?

[B]

Oh, sure.

[A]

This is weird. Sarah.

[D]

Sarah, here's weird. Here's where you got off on the wrong foot. And this is why we do this.

[A]

Yeah.

[D]

And why we're lucky to have Cal here is because you don't want to. We're trying to avoid the confrontation that he's just a one high guy.

[A]

We never. You gave it to everybody.

[D]

Structure here is that you're to going, going. Everybody gets one. Everybody's normal.

[A]

Agreed.

[D]

You too.

[A]

I noticed you're also a bit of a weirdo wearing a boy tie.

[D]

Hey, freak. Let me see it.

[A]

Cut that out.

[D]

Yeah.

[A]

Let's try again. And not a very. It would be weird for me if someone gave me a gift and went like, do you mind trying it on? I'd be really excited. I'll be like, what, I gotta dance now, too? Get out of here.

[F]

So what's a not weird way to ask that, though?

[A]

That's a hell of a question.

[D]

I. I think this. Let me see it on you. I don't think that's crazy. I think people, when they give you articles of clothing, I do think most people are excited to give and want to see you happy to have and then.

[A]

But you can also say, yeah, can you give.

[F]

Sorry, can you give it to him on a day that he's wearing a tie? Do you know when he's going to give like a deposition or Something.

[A]

Great question.

[F]

Then you say, hey, I have this gift for you. He opens it.

[D]

It's a tie.

[F]

You say, oh, my God, this would.

[D]

Look so good with the outfit you're wearing right now.

[F]

Could you switch it? And then tell them to go to the bathroom and look in the mirror? And then, oops, I spilled mustard all over your old tie.

[A]

That's an insane ending to a great piss.

[D]

What the hell happened at the end? I ate a sandwich over the old one while you were gone.

[A]

Everything besides the entire mustard thing, you.

[F]

Gotta get rid of it, Bernie.

[A]

No, we don't. No, we don't. We're not doing that insane ending. So, Cal and Sarah, can we go once more? Sarah, will you be influenced by Natalie's take there? Can we just see what happens?

[B]

Hey, Sarah. Yeah?

[F]

I think that's a great idea.

[B]

How was your break?

[F]

Oh, sorry. Hey, Connor. My break was good. How was yours?

[A]

Good.

[B]

Good.

[F]

Well, listen, I know I'm a little behind on the holidays here, but I got everybody a little gift. Here you go.

[B]

Oh, a tie. Thank you.

[F]

Yeah, you know, I got. You're welcome. I got. I got them for all the other partners as well. And you know it. Actually, I noticed you must have, like, a deposition or something today.

[B]

Yeah.

[F]

Oh, awesome. Well, listen, y', all, I'm excited about this gift. This is. Would you be willing to just try it on for me?

[B]

Yeah, sure. Does it not look too big?

[A]

It's an enormous time. It looks like an elephant's trunk.

[D]

This is for a man.

[A]

This is for a giant. I'm just a man.

[F]

You know, I'm not really sure. My husband helped me pick out the sizing, and he said this was, like, the normal size.

[A]

All right, Sarah. Yeah. This is gold. And now he comes back in wearing the tie. Love.

[F]

And then while he's up in the deposition, I snag the other one, light it on fire.

[A]

There, we got that. We got that. But now let's go ahead.

[B]

Cal, you. You got to give him a compliment once he puts the tie on.

[A]

So now Cal goes to the B. Or Connor goes to the bathroom. He comes back wearing the tie. He's a little insecure. It's not the one he likes.

[F]

Connor, that looks really nice. Good luck on your deposition today. I hope it goes well.

[A]

A little bit more.

[B]

More.

[A]

Yeah, that was. I'm. If I'm Connor, I got go. This looks terrible.

[F]

Okay. Okay.

[C]

All right.

[A]

Conor walks back in wearing the tie.

[F]

Okay. Wow, Connor, that looks so good. Oh, my gosh. Well, good luck on your deposition today. I know you'll crush it.

[A]

A little specific, sir. You mind getting a little specific in the compliments?

[D]

And I don't even hate you complimenting the new length of the tie, honestly.

[A]

Yeah. Or what it brings out in his eyes or. Holy cow. Kill Miller.

[F]

Okay. Well, Connor, Wow, that tie looks so good. The. The navy blue really complements the end in your Nike Monarchs.

[A]

That was mean.

[B]

You can get. You can give him the confidence directly. You can say something like, connor, that tie looks amazing. You're going to crush your deposition today.

[A]

Yeah.

[F]

Okay. Okay. We're just confident. Just like.

[A]

Yeah, yeah. Cause now you're killing it. All right. Connor walks back in the room.

[F]

Wow. Connor, that Ty looks so good, man. Good luck on your deposition today. You're going to crush it.

[A]

I'm happy with this. Is everybody happy?

[D]

I feel good. I feel. I feel pretty good about it. I think. I think we're in a good spot. I think. Don't be afraid to really make him feel good in that moment. The Nike Monarchs. We could do a whole other episode on that, but we gotta go.

[A]

And then. Sarah, will you. Are you going to do this before Christmas or after?

[F]

I don't know if I'm going to be able to do it before Christmas. Like get the ties after.

[A]

Yeah, it's. Then it's a gift for the new year.

[B]

Totally.

[D]

There you go.

[A]

Will you follow up with us as soon as it happens? This is going. This is something I think is going to work. And I want that bell ring.

[D]

Can I suggest one more thing?

[A]

Yeah.

[D]

How about because your husband helped you pick out, which I thought was a great little detail, get a picture for the husband and that picture secretly for the show.

[A]

Show, yeah, Totally.

[F]

That's a great idea.

[B]

Thank you, sir.

[D]

That's a great idea.

[A]

I think that's right.

[D]

Thank you, Sarah. Good luck. Go get.

[B]

Good luck, Sarah.

[F]

Thank you so much.

[D]

Enjoy the mo. For sure. Bye.

[F]

Bye.

[A]

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[E]

Yeah.

[A]

Do you know an easy place where you could build a website? Squarespace. Squarespace.com a sponsor of the podcast. We're here to help. Thanks, Elizabeth.

[D]

We adore Squarespace. My website is Squarespace. My other podcast, the Dollops website, is Squarespace. Every website I am associated with is Squarespace. I am currently working with one of the callers behind the scenes on a website. And we're going Squarespace because they do it all for for you. They make it easy for you to get involved in the website game. And you have to have a website. I mean, what are we doing here? They've got everything. They have cutting edge design, SEO tools. You know, I'm a big SEO tools guy. Search engine optimization, that's me, baby. If you want to set up a place for donations, videos, it's just every way you can up your legitimacy online, Squarespace is there for you. And like I said, right now, I'm working very closely with a caller and I am shark tanking her business. And we're using a Squarespace site. And we've used Squarespace on the show tons of times because user friendly, makes it look legit and can't say enough good stuff about it. I mean, that's why we talk about Squarespace all the time. So go to squarespace.com Gil sent me me for a free trial and when you're ready to launch, use offer code Gil sent me to save 10% off your first purchase of a website or domain.

[A]

This episode of We're Here to Help is brought to you by Booking.com. booking.com offers a wide array of hotels and vacation rentals across the US So you can find exactly what you're booking for. Oh.

[D]

Booking.com offers you such a wide array of options when it comes to vacation rentals, hotels, whether you're booking for yourself, whether you're booking for your. Your teenager like me, I'm my little boy, Gareth Jr. I'm booking him hotels through booking.com. booking.com makes it so easy. And then, you know, on the off night when I have to book a hotel for myself, booking.com right there. You know what? You're getting so user friendly.

[A]

Find exactly what you're booking [e-mail] booking. Yeah. Book today on the site or in the the app.

[D]

Hello?

[F]

Hello.

[D]

Wow. That phone was not on your proximity at all. Holy. Oh my God, the podcast. Can we get your name, please?

[C]

Yeah, Jim.

[D]

Hi, Jim, how are you? All right.

[C]

How's it going, boys?

[A]

Great.

[D]

Jim, how old are you, roughly? Buddy?

[C]

I am 42 years old.

[A]

Hey, Jim. Did you ever go by Jimmy?

[C]

Yeah, not really.

[A]

No. James? No.

[C]

Growing up, the. The grandparents would call me Jane Z, you know. Cute.

[A]

Yeah, it's just mostly Jim these days, huh?

[C]

Yeah, yeah. I mean, I'm 42 years old.

[A]

My brother gets mad at me when I call him Danny.

[D]

What you do?

[A]

I do on the podcast. My brother's name is Dan and he said, hey, my man. Ever since I was been eight, nobody calls me Danny. And I'll go like my guy Danny.

[D]

And now on the largest platform he's had, he's Danny. That's nice of you, Jimmy. Where are you calling from, bud?

[A]

James.

[C]

I'm in the. The western suburbs of Chicago. Grew up in the city.

[D]

Well, Jim, you've got Jake, you've got myself. And we have a great helper today. We have Cal Penn with us, so confidence levels high.

[B]

How you doing? Good to meet you.

[C]

It's nice to meet you. Yeah, I got, I got some good helpers here.

[D]

You're damn right you do. Well, speaking of which, what can we help you with, Jim? What's the problem?

[C]

Right. So about two years ago, I gifted a ring to my wife. I think it's a nice ring. One of those websites, you design it on your own. I think I did a bang up job. Sentimental. We have two kids. It's a birthstone for each of them on either side of the diamond and then, you know, an inscription on the inside of with their birthday. So something sentimental. Nice. I don't remember when exactly, but a couple weeks ago I clocked that she's not wearing it anymore. Still has a wedding ring and band. You know, no money problems really that are dire that would lead her to pawn it. So I'm kind of thinking either it fell out of favor or she lost it. What I think I could use your guys help with is, you know, sweet wife. She's the best. Obviously, you know, we're not afraid of confrontation. So she would have mentioned something to me if she wasn't feeling bad about it. So I, you know, I guess what, what I need to know is do I approach the subject with her? Yeah, I leave it alone because she obviously feels bad. I'm not trying to, you know, bury her or anything like that, but.

[A]

Yeah, well, first things first, Jimmy. Let me say I didn't hear Chicago at first, but now I do. Once you brought up the term your wife, you were, you went like, hey, my name is Jim, I'm 42. And then you went, I her a ring. My wife. I was eating sausage. With you going, I feel pretty nervous. But I'm excited about this weekend, boss. You know what I mean? So let me just paint this picture again just for my head because I got a little confused with the wedding ring versus this. So you got your wife. What kind of ring was this?

[C]

Oh, it's like a birthday gift. Two years ago to celebrate we had our second child. We're not gonna have any more. We made that decision. So it's just a nice birthday gift.

[D]

And we don't need to get to the second.

[A]

Where does ring number where she's supposed to wear it.

[C]

Right hand ring finger.

[A]

Okay, so you are covering up both ring fingers. You got the wedding on the left, you got the gift on the right. The left ring is still on the right finger. Mysteriously is empty.

[D]

Yeah.

[A]

Question is, what do we do now?

[B]

How long has it, has it been not on her finger?

[C]

Yeah, yeah, that's a good question. And I noticed it maybe a couple weeks ago, but I, I can't really pinpoint an exact date being Somewhat oblivious sometimes to this stuff.

[A]

Can we hear you say Caleb Williams is our greatest quarterback? Because I know. But I just walk into his accent, so pure in a while. But I haven't heard them say Caleb Williams and go, I like. Caleb Williams is a great quarterback. And I'm excited about Ben Janssen. Can we hear that the way Chicagoans would say it?

[D]

Sure. Then we'll get back in.

[C]

Caleb Williams is the greatest quarterback, and I'm really excited about this guy. Ben Johnson.

[A]

Yeah, that's pretty good, man. I feel excited to get back to where we were.

[C]

Park, Northwest side, Cicero, Montrose. You know, by the way, this is the.

[D]

This is the only ring Chicago fans should be focused on.

[C]

Hey, Gad.

[D]

Yeah, Jimbo. Hey, Jimbo.

[C]

Easy, pal.

[D]

I got something.

[A]

What is it?

[D]

I got a pitch. Okay. I would say what we need to do, I think. And look, yeah, you could simply ask her, but you're calling the show, so you don't want to. So I think we should make an organic moment where you can sort of discover it in front of her. And that kind of covers you for why you mention it. And the best way to do that, sort of to where Cal was going, is find out when she was wearing it. So go back through your pictures, take a look at your pictures. Take a look at the last time on your pictures where you see your wife wearing this ring. It's clear. And I would say one of two things. Either, for some reason, manufacture a moment where you've got to look for some picture in your phone, or maybe even better, is find a nice picture of her of you and her on your phone, get it framed, and then give it to her for Christmas. And in that moment. Moment, you can make the connection that.

[F]

Hey.

[D]

Where'S that ring? And set it up like an organic. Gotcha.

[A]

I got something.

[D]

Cal, you got a lot of silence on my pitch.

[B]

I'll be honest. I like that pitch a lot. I was taking it in because I. I felt like it. It was sweet. The reason I like that it was sweet is when I heard you telling the story about the ring. It was very. It. It was very sweet how you. You are so mindful that you don't want to hurt her by asking her. And I feel like if what you're saying is true, let's say she misplaced the ring and it's, like, been eating her up for the last six months or whenever she lost it. I think there's an opportunity to talk about gifting her something that has the same sentimental value, because obviously she didn't mean to lose it. Right. And so, like, there's. There's a way to do it that extends that kindness that I think the idea of that picture sort of brings out.

[A]

I gotta say. Jimmy is another guy from Chicago. I don't like any of this.

[D]

Yeah, I. I gotta tell you, man, I could tell that Jake's a little agitated by the emotional undercurrent.

[A]

No, Gareth is just doing a new thing where he's trying to be a sweetheart.

[D]

What are you talking about? I'll be honest. When Cal said my pitch back to me, I was like, that's way nicer than what I was doing. That was maybe. I was like. I was like, oh, yeah, exactly. Cal just does that.

[A]

Jimmy, here's what I would consider doing.

[D]

Yell at her, go ahead, Jimmy.

[A]

One day, walk in the house. What are we calling your wife? What's her name?

[C]

Jesse.

[A]

Jesse, go like this. Hey, Jesse. Jesus Christ. I got a pickle I want to talk to you about, babe. And she'll go, what is it? I'm over at the Jewel Osco. You'll go, let me tell you what it is there. Somebody must have broken into the damn house and stole some stuff. And she goes, what are you talking about? And you go, I'm missing things from my jewelry cabinet. She goes, what do you mean? You go, my necklace is gone. Five of my golden dollar bills are gone. Someone's stealing. Are you missing anything? And then she could say, I think somebody stole my ring. And now you're in it together.

[D]

You give her up.

[A]

Then somebody broke.

[D]

What is happen. Yeah, Cal, please.

[B]

This is an episode of Order.

[D]

Honestly, it's the wildest way to tell her to think that this all of a sudden, hey, honey, there's been a murder at home. No.

[E]

What?

[A]

We're trying to get Jimmy and don't listen to these guys. They're not from Chicago like us. We're trying to get her to believe somebody. Milwaukee, somebody broke in and stole stuff from you. And then you're saying to her, I don't know if it's true, but can you relate? And what we're hoping for, she goes like this. I gotta tell you, I think somebody. If that's true, I didn't want to say this to you, but you know that ring you gave me, I don't know what happened to it. And you go, I think it's the thief.

[B]

I think if you're going half, you can't go halfway. You gotta have a buddy come in with a fake gun and a ski mask while you're both home and just take. And then when you're doing the inventory, go. Oh, babe, I think they took your ring, actually.

[A]

That's interesting.

[D]

That opens up a new realm of idea. So what if we do this? Okay. What are you gonna say, Jim? Go ahead.

[C]

I was gonna say I got some cop buddies who might be able to get me a police report.

[A]

Jamesy.

[D]

What I would do is, to Cal's point, what if you employ a friend? What if a buddy of yours who's married comes over? While he's there, you're all hanging out, and he says something along the lines of, I actually want to get Judith this ring. You know, something that's like, you know, an anniversary ring. I'm thinking I could do the holidays or her birthday coming up. And that's when you go, oh, that's exactly what I got for Jesse. I got Jesse. Oh, my God. Where is that? Where is it? Like that.

[A]

That's really sweet. You know what we could do, Jimmy? We could use one of your cop buddies to contact your wife and go crazy. All right, Gareth, then I'll stop.

[D]

No, keep going.

[A]

I don't know what you're doing. Do you? Do you want to stop? Stop this.

[D]

No, keep going. Okay.

[A]

I would have one of the cop buddies contact your wife and go. You know, there's been reports on the blocks of possible things missing and break ins. I just want to know, has anything gone missing from you? We are not doing anything official at this point. We're not saying anything is happening. We're just getting an inventory of what's going on on that block of you, yours. Because if she's actually misplaced the ring and doesn't know it, she might not want to bring it up. But what she might be able to say is, yeah, actually, my ring has disappeared. You could get the cop and her to discuss it, and then we could get info. If she says nothing, not the case. Then she says to you and goes, have you heard about this? And you go, no. Then we at least know the ring is not missing. But the fact that we have the actual Chicago pd, who's a buddy of. Of yours, who's not afraid to do like, a Joe Pesi home alone type visit.

[D]

You know, I have a soft spot for home alone.

[A]

Well, it is the season, babe.

[D]

If you did it in person, if your cop buddy came over and was sort of talking about something that just. I mean, I just think if someone brings up a ring or something like that and you're there, that gives you reason enough to go. Wait a minute, where's. Is yours missing? Something like, like that?

[C]

It's not bad.

[A]

Where are you at, Jim? What are you kind of thinking?

[C]

Yeah, you know, I'm thinking the picture thing. Very nice. I like the new leaf there. Sweet Gareth. But I don't know how many like full body pictures I have where she's, you know, the hands are involved, stuff like that. I think the logistics of that, you know, might be a bit, little, little rough, I think. I think, you know, my cop buddies, we go back St. Pat's High School, so they'll, they'll hook me up, of course, but also I think, you know, we got, we got some holiday stuff coming up. I could maybe, I could maybe talk to like a family member, cousin, brother. Her brothers got a relatively new girlfriend. I could have him be like, hey, me, I could, you know, pull him to the side. Hey, help me out with this. Say you're shopping for a rink for your girlfriend and da, da, da, you could do there.

[A]

Oh, you know, you could, you know what you could do on that, Jim, is you could actually have your brother say to her and say, hey, can I see that ring that Jimmy got you? I want to get something similar to this girl I'm dating. Yeah, that could work because that could be very clean.

[B]

That's.

[A]

And then she goes, she. Then she could say to, to him, don't tell Jim, but I lost the ring. But if she gives it to him and we see it, then we can do a follow up to this to figure out why she stopped wearing it. But I feel like this could be in two parts, man. I think part one is we got to figure out, is the ring available? Because if she lost it. Sometimes it's hard to say. Like I'm such a goober. I, I don't even know where I lost it, but I'm really embarrassed. I don't want to deal with that.

[D]

The.

[A]

That's fine. And if that's that, we can get you out of it in an easy way. We could pitch a way to end it so it's not embarrassing for her. But if we know for sure she has it, then we figure out part two. And that is why isn't she wearing it?

[C]

Yeah.

[D]

Did you say that's her brother or your brother?

[C]

Oh, yeah, her brother, My brother in law. Her brother.

[A]

Great. So that's easy. Do you think he would play ball with you?

[C]

I think he would. You know, there's. We're gonna be out on the town for this big game coming up on Saturday. There's Packers. I can have a couple bruskies with him.

[D]

And.

[A]

You going old style. You going nice, new beers. What do you like?

[C]

You know, I like to mix it up, but, you know, they. They just introduced Yingling here in the Midwest. America's oldest brewery at. That's been. It's been in rotation.

[A]

You don't finish the night with a couple Malorts, do you? You're not an animal, are you, boy?

[C]

You know what? Actually, my dirtbag wife likes that stuff.

[D]

I can't handle it. Wait a minute. What handle it?

[A]

My dirt bag life. Talking about, what do you think about the rap song Dennehy? Have you heard that?

[C]

Oh, love it. Serengeti. Serengeti is the best.

[A]

So, Jamie, walk us through what you're going to do here, pal.

[C]

I think I'm gonna involve the. The brother in law.

[A]

Okay.

[C]

He's, you know, he's. He gets it, I think. I don't think he'll, you know, rat me out at all. I think he gets it. He'll help me out, play ball a little bit.

[A]

Great.

[C]

Like I said, he's got the girlfriend. Christmas is coming up. I think her. Her birthday's coming up, so. Yeah, I. I think, you know, like I said, chopping it up over a couple beers. Figure it out.

[A]

You know what you also said on this call that means the world to me. And I realize it's a Chicago thing. You said something affectionate about your wife. That doesn't translate. Our show's international, Jim. But you referred to her lovingly as, I believe, a dirt bag.

[B]

Yeah.

[A]

And I just want to say that's a term of affection and it doesn't translate my dirt back.

[D]

Also, Malort, enjoying the Lord at the end of the night.

[A]

Your wife likes Mallart is an amazing, great.

[B]

That's a great T shirt right there.

[D]

That is a good character description.

[A]

It is a great T shirt. Gal, before we get out here, what are you thinking about this? Are we right? Are we wrong? Have we missed the mark?

[B]

No, I like it. I think, look, if. If you. If for whatever reason you don't feel comfortable asking directly, if you don't feel comfortable going through the jewelry box when she's at work, if that feels like it crosses a line, I think this is the next best thing. You have a great relationship. Relationship with brother in law. You're going out on the town anyway. It's a great opportunity to figure out what's going on.

[A]

Yeah. And Jimmy, if she stonewalls him and he can't get an answer, fuck man, the boys in blue could help a lot in this situation.

[D]

Then we home alone, calling for backup.

[A]

Then we call in for backup. But before you call in for backup, call back in. Okay, for sure. And then before we go, could you say thin crust pizza? No, thank you. I'm from Chicago. Chicago.

[C]

Th crust pizza? No, thank you. I'm from Chicago.

[F]

Go Bears.

[A]

Go Bears.

[D]

Right there.

[A]

Anything about the Bears you want to say before we go? Any partying word? Can. Natalie, will you mute? Gareth, can you? Okay, thank you. So good. Go ahead, Jim.

[C]

I was just gonna say good, better, best.

[A]

Good, better, best.

[C]

Exactly what it's about.

[A]

All season, baby. It's gonna be a lot of fun. Jimmy, follow up with us, please. Thank you for doing the show.

[B]

We appreciate you guys. Thanks for having me.

[A]

It was a lot of fun. Okay, bye, bud.

[C]

Thanks, boys. Take care.

[A]

We're Here to Help is hosted by Jake Johnson and Gareth Reynolds. If you'd like to be on the show, please email us your question@ HelpfulPod Gmail.com. and if you want to watch video episodes of We're Here to Help, you can go to our [e-mail] to see our entire catalog.

[B]

We're Here to Help is produced by Rabbit Grim Productions executive producers Rob Hollis, Jeff Porter and Natalie Hollis associate producer Jesse Thurston. Editing, mix and master by Chris Faller.

[D]

Theme song by Oliver Raleigh. The COVID artwork is by James Fosdike, animations by Andrew Strelecki. And if you'd like to see Gareth do stand up on the road, go to garethreynolds.com Remember, all the advice given on We're Here to Help is for entertainment purposes only and all listeners should be adults and make their own decisions.

[A]

That was a hitgam podcast.

[F]

All video episodes of season one are available now on Patreon, and season two video episodes will be available every Monday starting January 20th. Go to patreon.com forward/hereto help pod.

[D]

Hi, I'm Drew Offalo. And I'm Dason Offuallo, and we host the Headgum podcast, two Idiot Girls.

[A]

Each episode we're discussing plenty of topics.

[F]

That you would be giggling at at.

[A]

A sleepover with your weird cousins. We talk about all kinds of things, like weird dating, horror stories, maybe a.

[D]

Really bad wedgie you had once, or even a show you're loving and anything in between. So you can listen to two Idiot.

[A]

Girls on your favorite podcast app or watch full video episodes on YouTube.

[D]

New episodes will be posted every Tuesday.