We're Here to Help – Episode 209: "Very Important Pickles & Twenty-Second Pilot"

Date: September 22, 2025
Hosts: Jake Johnson & Gareth Reynolds
Notable Guests/Callers: Ben (Florida) & Jen (Connecticut, Jenny and Benny's Pickles)

Episode Overview

Jake Johnson and Gareth Reynolds return for another episode of We're Here to Help, where they take listener calls and offer their best (if imperfect) advice. This episode features two standout dilemmas:

1. Ben, who wants advice on convincing his girlfriend to skip her childhood best friend’s wedding in favor of a Twenty One Pilots concert.
2. Jen, a pickle entrepreneur dealing with a copycat rival at her local farmer’s market.

The hosts bring their famously offbeat, supportive energy and comedic banter, offering creative solutions and plenty of laughs while rooting for their callers. As always, they blend earnestness with a refusal to take themselves too seriously.

Key Discussion Points & Insights

1. Opening Banter and Podcast Updates (00:24 – 10:00)

• Crowd Stories: Gareth shares a story about an "overzealous" audience member from a recent show ("the wowee girl"), highlighting how podcast catchphrases and inside jokes leak into real life.
  • “An audience member should not have a catchphrase.” – Gareth (01:19)
• Audience Engagement: Jake and Gareth discuss the strange but positive growth in their fan community and how their Patreon is influencing the podcast’s direction ("That’s the lab").
• Personal Updates & Stand-up Special: Gareth plugs an upcoming comedy special (Oct 4th, Chicago), discussing the difference between performing live stand-up for hours (“People like, you’ll like… Other times I’ll be like, ‘Alright, I’m going to get out of here.’ And you can tell people like, good. Awesome. Yes.” – 06:38)
• General Tone: Features their usual blend of mutual teasing, veering between sincere kindness and mock bickering, setting a playful, approachable vibe.

2. Ben’s Dilemma: Wedding vs. Concert (10:26 – 30:32, Follow-up at 54:16 – 73:03)

The Ask

Ben (24, Gainesville, FL) seeks advice on how to convince his girlfriend to skip her childhood best friend's wedding (with whom she’s not as close anymore) to instead go to a Twenty One Pilots concert. He already bought the tickets before realizing the wedding date's overlap; his girlfriend is excited about the wedding but isn’t passionate about the band.

The Hosts' Reaction

• Immediate recognition of the "impossible" nature of Ben’s request.
  • “This is bad. This is Everest.” – Gareth (11:20)
  • “You’re making her choose you over her friend.” – Jake (14:42)
• Reluctance but curiosity about possible solutions.
• Empathetic exploration: Is she in the wedding? Is it a rushed event? Is there a way for Ben to go alone?

Creative Solutions

• The PowerPoint Approach:

  • Gareth and Jake recommend Ben create a persuasive PowerPoint presentation, “Shark Tank” style, laying out the pros/cons of skipping the wedding for the concert.
  • Suggest including perks: nice hotel, dinner, money saved from the wedding budget, photoshopped images of the concert trip, even a cameo video from a band member if possible.
    • “How about we set Ben up with a PowerPoint to pitch to the girl? All the pros and all the cons, and I think the pros are you’ve prepped this… and then you start bringing up pictures.” – Gareth (16:02).

• Song Parody Pitch:

  • Jake suggests Ben write and perform a parody of a Twenty One Pilots song about skipping the wedding for the concert.
    • “The most popular song they have, I would like you to write new lyrics with the same melody and write a song parody about wanting to go over the wedding with her and perform it for her and dress up like the band.” – Jake (24:06)

• Delivery Strategy:

  • Reveal the predicament after getting her excited for the concert.
  • Make it funny and light to lessen the “ultimatum” feeling.
  • Positive, “no matter what, I love you” ending.

Ben’s Follow-Up (54:16 – 73:03)

• Execution: Ben creates the PowerPoint & the song. Walks his girlfriend through a multi-slide presentation, complete with photoshopped images, clear pros/cons, and concludes with a heartfelt, comedic song in a suit (“First time she saw me in a suit.” – 63:51).
• Outcome: His girlfriend is charmed, laughs throughout, and is swayed by the effort—she agrees to the concert, and they RSVP “no” to the wedding.
  • “She said the song really showed her how important this was to me. So, yeah, we’re going to the concert.” – Ben (66:34)
• Notable Surprise: Ben shares they got engaged a week later!
  • “So, she’s not technically my girlfriend anymore. We actually got engaged a week ago.” – Ben (67:15)
• The Hosts Celebrate the Power of PowerPoints: Encouraging the now-engaged couple to use PowerPoint for all major life arguments.
• Unique Offer: Jake offers to connect Ben to his brother (a professional wedding officiant), and jokes about the podcast crew attending their wedding.

3. Jen vs. The Pickle Copycat (30:40 – 53:55, Update at 73:59)

The Situation

Jen (25, Connecticut), co-owner of “Jenny and Benny’s Pickles”, faces a new competitor at her farmer’s market who’s obviously mimicking her every business move—from social media posts ("pickles at the beach") to logo shirts, sample strategies, titles (“World's Best Pickles”), and loyalty drivers (stickers/prizes for kids and pets).

The Hosts' Dissection

• Signs of copying are cumulative and blatant; Gareth and Jake sympathize and brainstorm ways to maintain Jen’s unique edge and curb further imitation.

Strategic Solutions

• VIP Loyalty Program:
  • Exclusive stamp card ("buy eight, get the ninth free"), humorously called “Very Important Pickle Person (VIPP)”.
    • “Make it like a joke, like it’s sketchy, like a drug deal… this is not for everybody.” – Jake (42:56)
• Confrontation:
  • Suggests directly and diplomatically addressing the issue with the rival, possibly via a humorous “pickle-off” challenge.
  • Create a fake “Farmer’s Market Council of America” IG account to prank/remind him about originality.
• Publicity Angle:
  • Turn the rivalry into the market’s feature event, encouraging a taste-test competition for "Best Pickle" (Pepsi/Coke-style) administered by the podcast.
    • “Challenge him to a pickle off… it’s a good way to confront him about this but also show off my pickles.” – Jake (47:42)
  • Record and share on social media for fun and transparency.

Update from Jen (73:59)

• Actions Taken:
  • Jen calls her competitor, addresses the copying, and finds he’s aware of the issue but remains friendly.
  • She proposes a "Pickle Face-Off" at the market; he declines, possibly out of intimidation.
    • “He unfortunately declined. So I think he’s a little scared, just saying. Which he has good reason to be.” – Jen (74:07)
• Moving Forward:
  • Continues her business with the hosts’ loyalty card suggestion.
  • Promotes her next farmer’s market appearance and encourages listeners to visit/follow her business.

Memorable Quotes & Moments

• On Audience Participation:
  – “An audience member should not have a catchphrase.” – Gareth (01:19)
• On Personal Growth:
  – “You’re making her say, choose me over your childhood best friend. You only get one wedding. I’m sure these 21 Pilots are going to perform for the next 20 years together…” – Jake (14:42)
• On Pickle Rivalry:
  – “I think you need to… say to somebody when you give it to them, ‘Buy one for 12, I’ll give you the second one for six.’ Then they don’t come back for the next week. We ice them out.” – Jake (41:32)
• On Creative Persuasion:
  – “The most popular song they have, I would like you to write new lyrics with the same melody… and perform it for her and dress up like the band.” – Jake (24:06)
• Victory Update:
  – “She said the song really showed her how important this was to me. So, yeah, we’re going to the concert.” – Ben (66:34) – “We actually got engaged a week ago!” – Ben (67:15)

Timestamps for Notable Segments

| Timestamp | Segment | |-----------|--------------------------------------------------------------------------| | 00:24 | Opening banter: Wowee girl, crowd stories | | 05:07 | Gareth plugs his comedy special | | 10:26 | Ben introduces his Twenty One Pilots vs. wedding dilemma | | 16:02 | PowerPoint/“Shark Tank” pitch idea is born | | 24:06 | Song parody pitch for girlfriend | | 54:16 | Ben’s follow-up, PowerPoint & song presentation | | 66:34 | Ben’s girlfriend agrees to concert, engagement news | | 30:40 | Jen’s introduction: pickle business rivalry | | 42:56 | VIPP loyalty program suggestion | | 47:42 | Pickle-off competition brainstorm | | 73:59 | Jen’s update: confrontation and loyalty card rollout |

Podcast Tone & Style

• Language & Tone: Candid, witty, and irreverent—full of playful digs, meta-commentary, and improvisation.
• Advice Style: Kind-hearted, collaborative, sometimes impractical but always supportive, with frequent emphasis on humor and creative presentation over traditional “serious” advice.
• Unique Flavors: Integration of pop culture (Shark Tank, band references), community-building, and willingness to follow up with listeners and root for their little life victories.

Takeaways for Listeners

• Sometimes, originality in small business is all about branding, relationships, and creative engagement (loyalty programs, fun events).
• When love and logistics clash, sometimes a heartfelt, creative pitch (even a silly PowerPoint and song) can turn the tide—especially if you make it personal and fun.
• The hosts reaffirm that “helping” isn’t about expertise, but about rooting for the caller and embracing the odd solutions that fit the heart of the problem.

For more, check out Jenny & Benny’s Pickles at the Walpole Farmers Market (Sept 27) or on Instagram (@jennybenny_pick).

Next Steps:

• Ben is off to the concert (and a wedding, eventually).
• Jen’s business is stronger (and quirkier) than ever; her copycat rival is respectfully scared.
• Jake and Gareth encourage listeners to keep calling in for more unconventional problem-solving.

(All timestamps MM:SS)