We're Here to Help, Episode 255: "Ugly Old Sweatshirt & Monitor Swap" (with David Krumholtz)

Date: January 28, 2026
Hosts: Jake Johnson, Gareth Reynolds
Guest: David Krumholtz

Episode Overview

In this lively and comedic episode, Jake and Gareth are joined by actor David Krumholtz for a classic double-helping of unqualified—but sincere—advice. As always, the trio brings open-hearted, sometimes tangential, and frequently hilarious support to listeners' dilemmas. Topics covered include maintaining maturity in long-running friendships, dealing with grown-up “gross guy weekends,” and the ethics of monitor envy in an office setting. True to the show’s spirit, the hosts riff with sharp humor, empathy, and plenty of mutual needling.

Main Segments and Key Discussion Points

1. Catching Up & Doppelganger Jokes

Timestamps: 00:17 – 06:14

• Jake introduces David Krumholtz as both a long-time friend, admired actor, and "brother from another mother" due to their similar looks.
• Playful banter about hair loss, past collaborations (including making out for an NYU student film as twins), and the odd actor “lookalike club.”
• Discussion of plastic surgery, the pressures of being “on display” as actors, and insecurities—delivered with self-deprecating humor.

“It’s almost disturbing, except you have a lovely head of hair and I am—”
—David Krumholtz (01:09)

2. Caller #1 – Steve and the Not-So-Golden Boys' Weekend

Timestamps: 11:08 – 33:13

a. Steve’s Cabin Conundrum

• Caller Steve from Montana describes an annual, 11-year-long tradition where high school buddies meet at a Forest Service cabin for a “get shitfaced” weekend that always turns into disgusting chaos—think beer-soaked Cheez-Its, smashed hot dogs, a “piss pad,” and a regrettable amount of cleaning.
• Steve’s dilemma: How can he get a gang of now nearly-30-year-olds to party but “class it up” and keep the cabin cleaner, without being the group’s nagging dad?

b. Details of the Mess

• The carnage doesn’t extend to bodily fluids inside but includes extensive food mess and general disregard.
• “Piss pad” outside the door, beer cans everywhere, meals destroyed—clean-up eats up half the weekend.
• Social shame: Steve feels embarrassed to tell his wife about the “grossness,” not the partying or jokes.

c. Host & Guest Advice Brainstorm

• Jake suggests camouflaging cleanliness as a game or challenge (throwing trash into bins for points, like a drinking game).
• Gareth adds a competition with consequences: last place does a full sweep-up in a “maid outfit.”
• David goes rogue, proposing Steve boycott the event (“let them suffer in their own mess”) or even stage a “boycott”—but this risks Steve realizing he isn’t needed.
• Group also jokes about fake emails from the Forest Service threatening to ban the group for their filth or about hiring a maid (“that’s so mean to the maid... she’d show up to 11 hammered dudes in the woods with no cell service!” - Krumholtz, 22:45).

d. Deeper Decisions: Outgrowing the Old Sweatshirt

• David pushes for mature separation—Steve should organize a more “adult” sub-group, break away, and leave the filth-lovers behind (“like an ugly old sweatshirt that just doesn’t fit anymore” – Gareth 28:56).
• Jake and Gareth remind Steve (and all listeners) that not all old friends remain “friends for life,” and “as you get older, the circle gets smaller.”
• Hosts analogize the group to an ill-fitting, stained sweatshirt: nostalgia won’t make it comfortable again.

e. Alternatives Considered

• Fake animal break-in (bears, tigers, “hot dog tiger,” or rats) to scare the group into cleanliness.
• Joking about the group as “drunk pig poachers” immune to all deterrents.

f. Steve’s Plan and the Hosts’ Closing Thoughts

• Steve agrees to plan a cleaner group outing, slowly “side-pitching” a new tradition with higher standards and less shame.
• Jake sums it up: “For the guys you love, plan a second trip... some will drift, others will stay. That's okay.” (29:10)
• The segment ends with practical, bittersweet encouragement: maturity sometimes means letting go.

“You’re hanging on to something you look bad in... it’s an ugly old sweatshirt.”
—Gareth Reynolds (28:56)

“As you get older, the circle gets smaller. Why am I in a bar with that guy? I’ve never liked him, he’s never liked me, but we’re just around each other.”
—Jake Johnson (29:23)

3. Caller #2 – “Monitor Swap”: Should Kyle Steal His Coworker’s Monitor?

Timestamps: 34:59 – 56:39

a. Kyle’s Office Ethics Crisis

• Caller Kyle, 22, from Massachusetts, works at a software company. He wants his friend/coworker Emily’s significantly better office monitor ("mine's from 2010, hers is basically new"), but they sit face-to-face.
• He jokes about "stealing" or swapping their monitors and seeks advice on how to do so “without getting caught.”

b. The Approaches Debated

• Gaslighting: Jake proposes the “classic swap-and-play-dumb,” i.e., switch the monitors, and if Emily notices, “What? No, these have always been here.”
• Framing the Boss: David ups the ante: blame the swap on management (“the boss decided, since I’m in more days than you...”).
• Victimless Crime: Gareth asks about swiping from someone else—the anonymous swap, but this is complex.
• Start a Movement: David points out the bigger issue: why are some getting stuck with junk monitors at all? Suggests an anonymous protest letter to management.
• Sabotage: Gareth floats “accidentally” breaking the old monitor during the coming office reshuffle; David says, “Break it right now.”
• Go to IT: Collectively, they realize, just ask IT; say “my monitor’s glitching,” and get a new one.
• Natalie (producer) breaks in with the smart take: “Just ask Emily—she might not care.”

c. The Podcast Prank Solution

• In a riff of meta-podcasting, the hosts propose Kyle make the swap, film himself doing it, and if caught, say, “It’s for the ‘We’re Here to Help’ podcast”—turning the whole act into a friendly, silly podcast challenge.
• Emily can only reclaim her monitor by hearing this episode and calling in. If not, Kyle keeps the monitor—“It’s not gaslighting if it’s a bit!” (Jake & Gareth, 51:01)

“If anybody catches you, say, ‘I’m doing this bit for this podcast called We’re Here to Help... It’s like a prank, it’s for the podcast!’”
—Jake Johnson (50:27)

• David and Gareth improvise a practice run, with Krumholtz playing a nosy coworker.
• The hosts cheerfully encourage Kyle to execute the “Monitor Swap Game” and report back.

4. Notable Quotes & Memorable Moments

Doppelganger Banter

“Mine’s going too. I’m on the M. Stuff.”
—Jake Johnson on hair loss (01:15)

“We made out... big deal for me. I’d never been on a set before.”
—Jake Johnson recalls NYU film with Krumholtz (03:09)

Cabin Chaos

“It’s like a frat house squalor kind of what it turns into.”
—Steve, describing the mess (13:39)

“Why are you sleeping in a one-room cabin with 11 guys who are filthy?”
—Jake Johnson, direct as always (28:49)

Outgrowing Friendships

“It doesn’t fit anymore—there are stains, there are holes in the pockets. You’re hanging on to something that you look bad in...”
—Gareth Reynolds (28:56)

Monitor Swap Shenanigans

“Isn’t the fake bet a gaslight though?”
—David Krumholtz (49:02)

“You want to do the swap with me? Everybody does these swaps.”
—Jake Johnson (48:31)

5. Advice Recap and Episode Takeaways

On Maturing Friendships

• It’s okay—and sometimes necessary—to let go of old traditions (or friends) that no longer fit who you are.
• Start new traditions with the people who respect your boundaries and values.
• Nostalgia isn’t always enough to excuse gross or regressive behavior.

On “Petty” Office Dilemmas

• Instead of conniving or gaslighting, often the best first step is open communication: ask your coworker, or simply approach management for an upgrade.
• If you can’t resist the prank, at least make it a good-natured “meta” game—be silly, not mean, and let everyone in on the joke.

6. Closing & Listener Follow Ups

Timestamps: 56:39 – end

• Jake invites both Steve and Kyle to report back—especially Steve’s wife, who is “the real winner here.”
• Gareth and David are delighted with how the episode’s “advice” surprisingly lands sweetly, not just as a bit.
• Epilogue: a nurse named Crystal calls in with real-world vasectomy aftercare advice, adding genuine—and humorous—bonus help.

Major Segment Timestamps

• Catchup, Doppelganger Banter: 00:17 – 06:14
• Steve’s Cabin Dilemma: 11:08 – 33:13
• Kyle’s Monitor Swap: 34:59 – 56:39
• Listener Vasectomy Advice (Crystal): 57:17 – 60:00

Episode Verdict

A classic “We’re Here to Help” blend of heartfelt advice, wild tangents, and uproarious comedy, this episode features standout chemistry with Krumholtz and the usual mix of ineptitude and wisdom. Whether you’re outgrowing your college buddies (and their beer-laced Cheez-It parties) or plotting harmless office high-jinks, Jake, Gareth, and David’s approaches—half sincere, half shenanigan—somehow land where good advice truly lives.

Memorable Quote:

“You’re hanging on to something you look bad in... it’s an ugly old sweatshirt.”
—Gareth Reynolds (28:56)