The JTrain Podcast — Chit Chat Wednesday: "Would You Date Across the Aisle?" ft. Daniel Koh

Host: Jared Freid
Guest: Daniel Koh, Democratic candidate for Congress (MA-6)
Date: October 29, 2025

Episode Overview

This Chit Chat Wednesday episode features a candid, wide-ranging conversation between comedian/podcast host Jared Freid and his friend Daniel Koh, who is making a run for Massachusetts’ 6th congressional district. The episode unpacks the realities of American politics, polarization, and the personal side of public service—often weaving in parallels to the world of stand-up comedy. The episode pivots around the question: can people (and specifically, can couples) meaningfully connect across political divides?

Key Discussion Points and Insights

1. Daniel Koh’s Political Background & Campaign (00:43–03:04)

• Jared introduces Daniel as an “expert in politics” and a long-time friend.
• Daniel lays out his experience: former Chief of Staff at Huffington Post, time at the White House, and service in local Massachusetts government.
• He frames his candidacy: “At the highest level, it’s giving good health care, making sure people have clean drinking water, people have affordable prescription drug prices. At the most local level, it’s making sure the town doesn’t go bankrupt…”
  (02:27)

2. The Problem with Modern Political Discourse (03:18–07:27)

• Jared and Daniel discuss why politics feels more divisive today—more than just getting older.
• Daniel blames both D.C. culture and social media: “Algorithms reward division… The cheap way to do that is to personally attack other people, because people will retweet it, whatever, it'll make news.” (06:29)
• Both note an unhealthy incentive for politicians and comedians alike to be “outrageous” for attention.

3. Communication Failures in Politics and Comedy (07:51–13:10)

• “The incentive isn’t to be a good comedian. It’s to do that again.” – Jared, on clickbait culture (08:26)
• Daniel draws comedy–politics parallels: “To make a funny joke that is genuinely funny and insightful is a lot harder than...make fun of someone's physical appearance.”
• Daniel urges for more thoughtful government explanations, especially on issues like healthcare: “What we don't do enough in government is be thoughtful and explain...what they do instead is look at these boogeymen doing xyz, but don't make the case.” (12:09)

4. The Human Side of Politics & Persuasion Fatigue (13:10–18:51)

• Discussing how hard it is to change minds: “You can see that they just don't want to talk to me anymore. They're just like, I am out. Just agree with me.” – Jared (14:02)
• Daniel notes the importance of knowing your neighbors and building relationships beyond politics.
• Critiques “statistic-citing” (“Democrats fail at...showing empathy or actually relating to people every day.”) and explains why security statistics don’t comfort individual victims (15:50)
• Boston’s “neighborhood model” for crime prevention: focus on community relationships worked better than just more policing.

5. Political Branding and Disconnect (18:51–21:59)

• “For the party that has most of the creatives, they're the worst at slogans.” Jared rails against slogans like “defund the police.”
• Daniel emphasizes his connection to his hometown and reluctance to be “sucked into” D.C. culture at the expense of local ties: “I love going to Little League games, and I love just like, hanging out with people at the Dunkin Donuts...far more meaningful than some like, stupid wine thing.”

6. The Politics Career Ladder & D.C. Status Games (21:59–25:28)

• Daniel unpacks “the prestige titles” inside the White House (“special assistant,” “deputy assistant,” “assistant to the President”), and the badge system—a “Hunger Games”-esque obsession with status.
• On the culture: “What they care about is that their passport isn't being processed on time...not what committee assignment I’m on.” (22:54)

7. Connecting with Voters—Fundraising, Authenticity & Burnout (26:01–29:52)

• Jared reads Daniel’s campaign text to highlight authenticity (“Text STOP to quit—I don’t quit nothing.”).
• Daniel shares practical campaign realities: “You could be the funniest person in the world, but if you can't afford a microphone so that you can speak into something…in the case of a campaign, if you don't have the money to print a mailer...it'll be very hard for you to get your message through.” (28:00)
• Michelle Wolf’s comedian/politician parallel: “The only people that see the whole country are politicians and comedians.”

8. Should Politicians & Voters Be Friends Across the Aisle? (29:52–32:54)

• Daniel describes the value of civil relationships across party lines: “There’s absolutely no reason why you can't highly disagree with someone and also just have a good relationship with them.” (30:36)
• Pushes against the idea that bipartisan amity equals collusion, calling it “very conspiratorial.”

Listener Advice Segment: "Would You Date Across the Aisle?" (32:54–42:13)

(Emailer’s Question at 32:54):
Can a very liberal woman date a “moderate” man if she’s worried moderate just means “closet conservative” and values won’t line up?

Daniel's Advice:

• Rejects the idea that party label tells you everything: “There are a lot of people who care deeply about social justice issues...who don’t like high taxes and think that government sucks...party affiliation is not the bellwether.” (37:26)
• More meaningful is whether a person truly cares about equality and supports their partner: “It's where your values are and how you view the partnership.” (39:08)
• Jared emphasizes specificity over labels and urges listeners to “get specific about the things you care about and…bring up examples.” (40:20)

Daniel on modern relationships and ambition:

• Describes the real-life balancing act as parents and partners: “Somebody has to sacrifice…there’s no such thing as work-life balance in many cases.” (41:09)
• “That’s not a Republican or Democratic thing, that’s just a values thing.” (42:08)

Game: "King of the World" Policy Lightning Round (43:02–54:18)

Jared presents Daniel with several real-life issues and asks, “If you were king of the world, what one change would you make?”

• Trains: “I would rather have a slower train that I know is going to arrive at South Station at 5:30 every single day than some like bullet train…predictability matters.” (43:55)
• Bathrooms on Trains: “Make the bathroom sliding door not fly open...that is always my biggest fear.” (45:36)
• Roads: “Solar paneled roads that would melt the snow automatically...it’s so expensive, but in theory, that’s pretty cool.” (46:46)
• Debates: “Too much of the 42-second mic drop for social media...I would try to force or incent people to actually make data- or fact-based arguments versus just red meat.” (50:28)
• Internet: Daniel laments the stall in broadband improvement: “We got to a certain point of technology and it seems like it’s just stopped.” (53:40)
  Jared’s wish: “I wouldn’t let anyone below the age of 18 on the Internet,” arguing that anonymity and trolling are too easy for kids.

Notable Quotes

• Daniel Koh on D.C.'s Immaturity:
  "The amount of immaturity that happens in D.C. on both sides of the aisle—candidly throwing ad hominem attacks, ... just shouting at people—is not what we were taught when we were six years old." (05:50)

• Jared Freid on Social Media Incentives:
  "Now the incentive isn't to be a good comedian. It's to do that again." (08:27)

• Daniel Koh on Political Empathy and Crime:
  "Democrats fail at...showing empathy or actually relating to people in every day...To tell someone, 'Hey, statistically you're safer,' that is not helpful." (15:50)

• Daniel Koh on White House Status:
  “The correlation between what you do and these titles [in the White House] are not that linked, but they kind of are...People get all insecure about that.” (21:59)

• Jared Freid on Slogans:
  "For the party that has most of the creative and writers and Hollywood people, they are the worst at doing slogans. 'Defund the police.' I'm like, how could you think that's getting you where you need to go?" (18:04)

Timestamps for Important Segments

• 00:43 — Daniel Koh introduction and political background
• 05:41 — Why people are tired of politics; D.C. culture and social media
• 11:21 — Drawing clear comedy/politics parallels about divisive incentive structures
• 15:12 — How to actually reach and relate to people in policy conversations
• 18:51 — Political branding and living between D.C. and Massachusetts
• 21:59 — White House careerism/status games
• 26:01 — Political fundraising and text campaigns
• 32:54 — Listener advice: “Would you date across the aisle?”
• 43:02 — “King of the World” policy game begins
• 50:28 — How to fix political debates
• 54:18 — The problem with letting kids online

Overall Tone & Flow

The episode is engaging, colloquial, and alternates deftly between comedy and earnest policy discussion. Jared keeps the tone light, inserting comic analogies and “games,” while Daniel remains open, self-aware, and practical—eschewing talking points in favor of personal anecdotes and real talk about both political and domestic life. Both speakers bounce nimbly between relatable “real talk” and policy deep-dives, reinforcing the core message that ultimately, we can and should connect across divides—whether political, regional, or even romantic.

Recommended for:
Anyone curious about the personal side of politics, how comedians and politicians see America, or whether bipartisanship can exist in real life (or in your love life). The episode is especially insightful for those ever stumped by the question, “Would you date across the aisle?”