Happy Hour: NYC's Hottest Date

Summary

---

Kennedy Saves the World — “Happy Hour: NYC’s Hottest Date”

Date: September 12, 2025
Host: Kennedy (Fox News Podcasts)
Guest: Walker Ward, creator of Pedicab Connections

---

Episode Overview

In this upbeat “Happy Hour” episode, Kennedy sits down with Walker Ward, a former Wall Street financier turned unconventional matchmaker on the streets of New York City. The discussion centers on Ward’s radical career pivot: trading financial spreadsheets for the handlebars of a hot-pink pedicab—dubbed the "Chariot of Desire"—as he connects single New Yorkers craving genuine connections in the age of dating apps.

Together, they explore the struggles of modern dating, the value of spontaneity, and finding authenticity (plus a little humor) in the search for love. The episode captures Ward’s innovative approach to matchmaking and his commitment to fostering IRL experiences in our tech-obsessed culture.

---

Key Discussion Points & Insights

1. From Wall Street to Pedicab Matchmaker ([00:10]–[03:18])

• Walker’s Background: Once a successful six-year Wall Street employee (“sell side”), Ward reveals he was let go in July 2023. This life shift, plus encouragement from his girlfriend, pushed him to pursue entertainment and eventually build his dating project.

  • Notable Quote:
    “Everything happens for a reason. That kind of thing. I was let go.” — Walker ([02:04])

• The Social Media Leap: Instead of following the usual audition path, Ward began posting comedy sketches online, which ultimately snowballed into his street-level matchmaking concept.

• The Spark of Inspiration: Observing New Yorkers glued to their phones, Ward wondered:

  • “There are so many amazing people walking by each other…If they were just looking up, you never know, you might meet your potential person.” ([04:04])

---

2. The “Mingle Mobile” & Organic Love ([03:18]–[08:38])

• Concept and Mechanics:

  • Ward pedals a neon pink pedicab through Lower Manhattan, inviting singles to hop in for short, curated “dates.”
  • He plays host, asking questions, creating a fun, low-pressure environment (“shopping for love”).
  • “Worst case scenario, you get a free ride.” — Walker ([04:55])

• Success Rate:

  • He reports about a 50% success rate for number exchanges and first dates—better than most bars or apps.
    • “Once I have someone in the backseat…it's about 50%.” — Walker ([05:11])

• Why It Works:

  • The vibe is spontaneous and playful; people are more open to genuine conversation in real life than through apps.
  • Kennedy exclaims, “That’s got to be higher than going to a bar or getting on an app.” ([05:40])
  • Ward argues: “There’s something about being in a funny, spontaneous situation… you might just give them a shot.” ([05:45])

---

3. The Dating App Fatigue ([06:22]–[07:07])

• Culture Shift: The guest and host riff on the frustration many feel toward gamified dating, ghosting, and lack of authenticity.

  • Kennedy: “Why are people playing games? Like, there’s got to be a better, more honorable off ramp than just ghosting someone.” ([06:40])

• Real-Time Chemistry: Ward’s approach is all about real-time, face-to-face chemistry — “Butterflies…like a lightning bolt.” ([06:22])

---

4. The Backseat Matchmaking Process ([07:10]–[12:50])

• How the Pedicab Date Works:

  • Quick rides (15–20 minutes), complete with a “Just Met” neon sign.

  • Conversation starters span “dating history” to playful or more direct intimacy questions, depending on the vibe.

  • The “Prisoner’s Dilemma”: Each participant secretly votes (with a paddle) "go" (green) or "stop" (red). If both choose go, Ward drops them at a date spot.

  • Notable Quote:
    “I have these little paddles...one side is stop, one side is go. They close their eyes. I count them down. 3, 2, 1. Do you want them to be a match? Yes. No.” — Walker ([07:42])

• Safe Words: To allow an easy exit, each “hero rider” can invoke a prearranged signal (“chicken tendies”) to discreetly end a bad pairing. ([12:50])

• Typical Night: Usually, a single rider will meet up to 3 potential matches per session.

---

5. Word of Mouth, Fame, and Expanding the Brand ([13:10]–[14:25])

• From Random Encounters to Reservations: Initial outreach was done by patrolling for potential riders. Now, locals DM him to schedule rides, turning him into a local dating celebrity.

  • “People are like, ‘Hey, I’m single. I’m going to be here this afternoon. Can you pick me up?’” — Walker ([13:34])

• Brand Expansion: Kennedy highlights the creative, monetizable potential for Ward’s brand (a safe, funny space for magical moments).

---

6. Seasonal Challenges & The Future ([15:43]–[18:30])

• Weathering NYC:

  • Ward acknowledges the need to winterize his pedicab—"make a little snow globe"—for colder months, drawing inspiration from Central Park’s horse carriages. Suggestions include fleece blankets, hot chocolate, and perhaps Baileys. ([15:56]–[16:33])

• Neighborhood Boundaries: Currently focused on downtown (West Village, Greenwich Village, Soho). Avoids Midtown/Central Park due to rivalry with “territorial” traditional pedicab drivers.

  • “The real pedicab guys…don’t like—they’re territorial and you know, my ride is free.” ([18:30])

---

7. Community, Connection, and Next Steps ([14:25]–[18:55])

• Measuring Success:

  • For Ward, a “win” is two people having a real, in-person conversation and exchanging contact info.
  • He’s considering follow-up episodes to check in on past pairings (e.g., “Did it work out? Will you hop back in [the cab] and we’ll go for a check-in ride?”). ([14:32])

• Seasonal Optimism:

  • Ward is excited for NYC in the fall (“my inner PSL Girly comes out…can’t even control the heel kicks”)—hoping for more matchmaking success with larger crowds. ([16:46]–[17:17])

• Where to Find Walker Ward:

  • Instagram: @pedicabconnections ([17:50])
  • “You can usually find me riding around the West Village, Greenwich Village, Soho. Right now I’m staying away from Central Park…” — Walker ([17:55])

---

Notable Quotes & Moments

• “I was doing well on Wall Street. ... I actually did not leave on my own volition. I was fired.”
  — Walker ([01:21])

• “There are so many amazing people walking by each other every day. ... If they were just kind of looking up, you never know, you might meet your potential person.”
  — Walker ([04:04])

• “Once I have someone in the backseat…success rate is about 50%.”
  — Walker ([05:11])

• “That’s got to be higher than ... going to a bar or ... getting on an app.”
  — Kennedy ([05:40])

• “I have these little paddles…one side is stop, one side is go. ... Do you want them to be a match? ... And they hold up green or ... red.”
  — Walker ([07:42])

• “You pull up on a group of ... the girlies who are outside and deleting an Aperol spritz on a Thursday ... and usually what happens … they force their friend in; takes a little bit of the lift off of me.”
  — Walker ([10:51]–[11:51])

• “You got to be consistent. People start to recognize you … so now ... people are starting to recognize.”
  — Walker ([11:20])

• “I mean, this could go in so many directions ... just in terms of monetizing what you’re doing, the brand you’re creating…”
  — Kennedy ([13:54])

---

Timestamps for Key Segments

• Walker’s Origin Story: [00:10]–[03:18]
• Matchmaking Mechanics: [04:52]–[08:38]
• Dating App Fatigue / Seeking Real Connections: [06:22]–[07:07]
• In-cab Rituals & Success Rate: [07:10]–[08:38]
• Safety/’Safe Word’ Protocol: [12:50]
• Evolving from Outreach to Demand: [13:10]–[13:54]
• Weather & Seasonality Discussion: [15:43]–[16:46]
• Finding Walker / Neighborhood Boundaries: [17:44]–[18:30]

---

Tone and Takeaways

• Kennedy’s Style: Warm, witty, conversational, and effusively supportive of innovative thinking.
• Walker’s Vibe: Self-effacing, energetic, and genuinely enthusiastic about helping New Yorkers skip the swipe and find “real” moments.

Ideal For: Listeners weary of digital dating, those who crave old-school serendipity, or anyone interested in adventurous entrepreneurship with a human touch.

---

End notes:
For updates or to join the adventure:

• Instagram: @pedicabconnections

Kennedy proclaims: “We love, love.” ([17:45], [18:55])

---

Transcript

[A]

Foreign.

[B]

Hello, and welcome to this episode of Kennedy Saves the World. Obviously, everything is a giant storm right now, and I think we need a ray of sunshine. I think we need a little bit of hope. And this happy hour, I'm going to talk to a young man who completely changed his life in order to help other people find love. And you're like, oh, is he a. A matchmaker? Does he sit in an office and look at headshots and create algorithms? No. He was a. A well off, well heeled finance bro who left Wall street invested in a pedicab. He pedals around with single people and helps them find other single people he thinks might match them well. And it's all about alchemy. I always say it. You gotta look people in the eye, you gotta smell their pheromones in order to know whether or not that person is the right partner for you. So this episode of Kennedy Saves the World Toasts. Walker Ward.

[A]

Cheers.

[B]

Welcome to the podcast.

[A]

Let's go. Honored to be here.

[B]

A bit of a mule.

[A]

Yum. Cheers.

[B]

Everybody might be a little gray goose in there.

[A]

Good. For old times sake. I love it.

[B]

Yeah, that's right. The goose is loose in the studio. So you were doing well on Wall Street. Was it soul crushing? What was it about your time there that made you want to leave and completely reinvent your life?

[A]

I was. Well, first of all, thank you so much for having me. I'm excited to be here. I just came. It's fashion week here in New York between us girls, as we know, and I just came from my first ever Runway show, which was cool. So I'm a little more dressed up than usual, and I'm excited to be here. But long story short, I. Well, is a relative term. But, yes, I was doing well on Wall street sell side. And I actually did not leave on my own volition. I was fired.

[B]

Oh, that sucks.

[A]

I was let go July of 2023.

[B]

Okay.

[A]

And then so about.

[B]

So you think. You think you're fine, You've made it through the pandemic. A lot of people still want to say, stay home. You're like, I'm one of the brave ones. I am still here. I'm good to go.

[A]

And I had been there for about six years, so it's not like I was, you know, brand new to the firm and everything, but whatever, you know, everything happens for a reason. That kind of thing. I was let go. And my girlfriend, about a month later, I'm looking for similar jobs. You know, I'm like, okay, let's Go find competitors I could apply to or leverage my network that I built. And my girlfriend, who's amazing, she was like, Walker, you've always loved entertaining. You've always loved performing. I have always wanted to be, like, a film or television actor personality. And, you know, in today's world, rather than just waiting tables and going on auditions, you can kind of get your name out there through social media. So, long story short, that was the impetus for my social media journey in general. I started doing skit, like, sketch comedy characters, that kind of thing, which snowballed into late this past spring, 2025. You know, I was just. I have a lot more free time on my hands than the structured 9 to 5 employee. So I'm walking around New York, and I.

[B]

So you're one of the people I see at the gym at, like, 2 in the afternoon.

[A]

I'm at the gym at, like, high noon.

[B]

Yeah.

[A]

You know, maybe just at a leisurely stroll from my apartment kind of thing. I have the time, so. Which is great. And I'm looking around the streets of New York, and I'm like, God, everyone is so buried in their phones and their technology. Not necessarily anyone's fault in particular, but just culturally, we're so A to B, check the box, get to where you got to go. And we're kind of buried in our tech. In our tech.

[B]

Yeah. And try and complete 16 tasks all the way. Yeah.

[A]

As we go, you know? And so, long story short, where I'm going with this is I was like, okay, maybe it just. There's so many amazing people walking by each other every day. If they were just kind of looking up, you never know, you might meet your potential person.

[B]

Everyone who doesn't have. Who's not in a relationship right now is frustrated, and they're looking for another person. And they're like, I'm doing all the right things. Why is it so hard for me? Like, there are millions and millions of people in the city. At least half of them are available. Why can't I meet the quarter that might be a good match for me?

[A]

Precisely what I.

[B]

So you're looking at the math. Your analytical finance brain is running the numbers.

[A]

Call it 8 million people and everything. You just said call it 8 million on average, let's say 4 million. Or are single, let's say a million, are walking around the streets of New York every day. I wanted to sort of put a little bookmark in between someone's, you know, kava run, and they're getting back to their office or something. Pick them up, hop in the back of the mingle mobile or the single sled.

[B]

I love the single sled.

[A]

The chariot of desire.

[B]

The chariot of desire.

[A]

The chariot of desire. And just, you know, you never know. Worst case scenario, you get a free ride. I have learned that. Well, basically what I like to do is I like to treat it like we're shopping for love. So if someone hops in the backseat.

[B]

They know what they're getting into.

[A]

They do. Totally. And sometimes people ask me, what's the success rate like? And once I have someone in the backseat, the success rate meaning do I find them a match? A match being you exchange numbers, you like each other enough to go on a first date. Obviously you're not just gonna maybe propose in the backseat, but you never know. Regardless, you're not opposed to it. That can tell rate. Oh, certainly not. Is about 50%. Probably like 50% of the people we get in the backseat.

[B]

That's got to be higher than A, going to a bar or B, getting on an app.

[A]

Totally. And I think. I think there's something about being in a funny, spontaneous situation like that where even if you might not be hitting it off beautifully with the person you're on the date with, it's like, wait, this person was down to earth enough, cool enough to hop in the back of this pedicab. This person was cool enough to hop in and meet me. Let's give him a shot. So anyway, one of the common things I hear all the time is that, you know, dating apps are just getting crazy and people are sick of them. And why not just tap back into the organic. To your point, pheromones meeting in life, in the world, in the wild, Butterflies.

[B]

Like a lightning bolt.

[A]

Totally not something where a true organic meeting as opposed to something where you meet somebody on an app. Okay, they sent me a message. Little dopamine rush, I'll get back to them in a day or something. It sort of forces you to be present and engage.

[B]

I don't like those games either. I can't stand the timelines, and I'm gonna make someone wait. And I was talking to a friend of mine the other day. She's like, I met this guy last night, and we hit it off. We had a great conversation. He texted me the next day. I text him back, and I haven't heard anything from him. And I was like, why are people playing games? Like, there's got to be a better, more honorable off ramp than just ghosting someone.

[A]

Totally. That's where the mingle mobile comes in.

[B]

Maybe so, so what happens when people connect? What does it look like?

[A]

Basically, what it looks like is. So what it looks like is I have on the back of the mingle mobile, the single sled, a little Just met neon sign, a little play on just married. And I like the way we determine if it's a match is I like to keep the dates between 15 and 20 minutes, so it's not that long. And I'll ask them questions we're looking for love, et cetera. Ask them about their dating history and let them talk and get to know each other.

[B]

Do you ask them about the dating history when they're both together?

[A]

Not sometimes separately. Sometimes definitely. The first person who gets in the hero rider, as I call them, you know, let's say Sarah gets in the backseat. I'm like, you know, sarah, what up? Talk to me. What's the deal? And usually not all the time, but someone who is willing to get in the back of a hot pink pedicab with a single heart bouncing around and this fuzzy guy driving it, someone who's willing to get in there to look for love, has been through something, or they're actively dating, looking for someone. You know, you're not gonna get back there if you're not. So I'll get to know them. And then for the match itself, I have these little paddles that have stop octagons on the top. One side is a stop sign, one side is a go sign. Green, red. They close their eyes. I count them down. 3, 2, 1. Do you want them to be a match? Yes. No. And they hold up green or they hold up red, or one holds up green, one holds up red.

[B]

Prisoner's dilemma.

[A]

Which happens. But anyway. And if it is a match, then I like to take them to a little spot. There's a longer story to this, but I like to drop them off at a date spot I try to work with. I ride around a lot in lower Manhattan. I live in Lower Manhattan.

[B]

When you say lower Manhattan, do you mean like the East Village or like Fi Di?

[A]

More. More village. More Greenwich Village, West Village, Chelsea, soho. That's the area that I know very well just because I live there. So. So I know the roads well. I know restaurants. So what I've learned since you asked is in the beginning of the rides and of the show that I call it, you know, pedicab connections. I was doing it midday and like, that did not lend itself well. People were just busy. Even though I want to try to pull someone out of their day to day, morning or early Evening, evening. Evening is the hot spot.

[B]

That's like being on safari because that's when the animals are most active. They don't take you on safari rides in the middle of the day. You're not out there looking for giraffes humping at noon. Concrete jungle safari in the morning, like 6, 7. Or you do it as the sun.

[A]

Is flirting with setting 100% as day flirts with night. When I come out and what I've learned and noticed is I have the most success. The hardest thing to do is get someone in. Just. I get it. You know, some random guy pulls up to you, you like hop in. You think there's a price associated with it. It's a pedicab. Yeah, it's a free ride scam. Free ride. It's a scam.

[B]

But wake up in a bathtub full of ice in Thailand, it's not good.

[A]

Bangkok, you pull up on a group of. I like to try to get a girl, woman, etc in the cab first. Because it's easier to pull up on someone with a woman in the backseat than a guy usually.

[B]

Yeah. Two guys. It's like predatory, right?

[A]

Exactly. It has a little bit of an. It can have that feeling. We don't want that. So I try to look for, you.

[B]

Know, the girlies that could seem to a woman like a dare on a.

[A]

Bachelor party or like a fantasy football, like you lost a fantasy football league. You pull up the people and like pick them up. But anyway, long story short, I'll look for groups of the girlies who are outside and deleting an Aperol spritz on a Thursday Friday evening. And usually what happens, Luckily I've, you know, you just, you got to be consistent. People start to recognize you and you keep doing something. So now between the Instagram page pedicab connections and then just seeing me in the wild during our safari, people are starting to recognize. It's a little bit more of a familiar thing.

[B]

Don't go anywhere more. Kennedy saves the world right after this.

[A]

So when I pull up outside of a restaurant in West Village or something or Greenwich or Soho or wherever, it's like the non single friends in the group are pushing the single friend. So you'll see like, oh wait, that's the guy. Then like you can see like a girl with like a rock on her fingers.

[B]

Like I read about get in and.

[A]

They force their friend in, which is great. It takes a little bit of the lift off of me to the pitch.

[B]

Yep.

[A]

And the friends kind of do it for them. And Then you're pre vetted. Pre vetted, Baby pre vetted. And I get to know. Get to know them and then what they're looking for, what they're not looking for. You know, how, how honest are people.

[B]

Like, how, how easy it is to read someone who's in the back of the pedicab.

[A]

Yeah, I pretty. I mean, people definitely will if I ask them, like, what are you looking for? Or like, you know, sometimes if you want to turn up the heat, we'll ask him, like, what's a turn on for you? Or something. And they'll, they'll go into like the sort of generic PR answers kind of like, oh, like intelligence or, oh, like that. Which is like, fine, I get it, you want to be with an intelligent person or whatever. But like, let's get down to brass tacks. What, as we say, you know, what moves the needle in the bedroom kind of thing. If we're trying to keep things up, if we. It's all based on if I feel the date is going well or not.

[B]

Yeah.

[A]

And then I'll have a little safe word with the hero writer. Well, they'll be like, you know, chicken tendies or something. And now if I hear chicken tendies, I know it's not going well, then we kick the other person out, try to find somebody new.

[B]

So what's the most you've had the hero writer? How many suitors have you had the hero writer meet in one go round?

[A]

That's a good question. Probably like three.

[B]

Okay.

[A]

It's not now. What's happening is people are starting to reach out to me. I don't just have to wake up, fire up the minglemobile and ride around looking for people.

[B]

Fingers crossed. Hope for the best, right?

[A]

I'm starting to wake up now, which is kind of cool. People are like, reaching out.

[B]

I'm beyond the corner of room and.

[A]

Exactly. And they're like, hey, like, I'm single. I'm going to be here this afternoon. You know, my girlfriends and I, or the boys and I, we're going to dinner here. Can you pick me up? And I'm like, sure. So. And that makes it easier for me because, like, I've got my little. I'm building my little Rolodex of singles in New York. And it's pretty. It's pretty cool.

[B]

I mean, this could go in so many directions just in terms of monetizing what you're doing, the brand you're creating, and where you could go from this outside of the pedicat, which is It's a great hook. Like, it's perceptually. It is a wonderful way for people to know that they've got a safe and funny place to go where something magical might happen. How long have you been doing this?

[A]

Like, early July, late June of this summer was the first time I did it. It's brand new.

[B]

Do you have anyone who's in a relationship now? Like, what is your success rate? What does success look like for you?

[A]

Good question. I. I have. I'm trying to work on what the best format is for follow ups because people want to. Sometimes I'll have people reach out just who've watched an episode and they're like, wait, what happened to Kim and Maggie? Or what happened to Peter and John? Or like, whatever. And so I need to figure out like maybe I do like a month, month or two month check in. Like, hey, are you guys. Did it work out? Did it not? Will you hop back in and we'll go for a check in ride?

[B]

Yes.

[A]

We're now getting to the point being a couple months in where that we can do that. It's been a little too early to actually do the follow ups, but now I want to know. Yeah, so, you know, I get everybody's number and Instagram who come in the cab and I'll start reaching out to them soon. But so anyway, I mean, success. What does success look like to me? Just if I can get two people in the back seat to have a good conversation, to try to find. Find some organic, natural convo and a connection in the backseat and they exchange numbers and they go on a date, that's success for me.

[B]

What will you do when it rains?

[A]

That's a good question.

[B]

And when the weather starts to get consistently colder because we're now entering into coffin season, Coughing season could be very, very good for you. But how do we maximize that?

[A]

We gotta winterize the Ningleva.

[B]

That's right.

[A]

I don't. I got to go to like a trailer park or like a Winnebago area and like, figure out how I can winterize this thing. Make a little snow globe. Yeah.

[B]

Yeah. Oh, my gosh. That's amazing.

[A]

On the sled. We're like on a little sled Santa sleigh. I mean, there are all kinds of places I could take that. I don't. Between us girls, I don't know yet. I'm not sure what I'm going to do when it gets to me.

[B]

Maybe talk to some of the. The horse and carriage.

[A]

Yeah.

[B]

Folks in Central park because they're they're year round.

[A]

Totally.

[B]

So maybe it's like big polar fleece blankets, little bit of a portable heater.

[A]

Hot chocolate, you know, maybe some Baileys.

[B]

In there if they want it.

[A]

For old time sake, baby. Hell yeah. I love it. But that's the, that's basically the format. That's what we've been doing. I, I personally am excited. Fall in New York is my favorite.

[B]

It's magical.

[A]

They're truly nothing like my inner PSL Girly comes out pumpkin spice latte. I'm just like, you know, can't even control the heel kicks. Involuntary involuntarily. They're coming out on the sidewalk of all my layers and anyway I. So it's because it's been hot when I've been riding in the summer. So I'm excited for that like 50, 60 degree day. I also think Saturday like weekends are going to be really big now that a lot more people down in those neighborhoods have returned from their respective summer travels.

[B]

Yes.

[A]

You know, they're outside watching college football. They're outside watching the NFL. Just the streets from a fishing perspective. Not catfishing, but fishing for love. As the, as the pilot up in the cockpit. It's much, I'm noticing. It's much. There are more people around. There are more fish floating around that I can try to get to hop in the backseat.

[B]

Well, I love your venture. I love love.

[A]

Thank you.

[B]

I love it.

[A]

We love love.

[B]

Walker war. Where can people find you if they want to hop in? The chariot of desire.

[A]

Totally. So Chariot of desire. Petty cab connections on Instagram.

[B]

Okay.

[A]

On social media, if you're looking for me, that's where you can find it. Petty cab connections. P E D as in dog. I pedicab connections. And then in the world we're usually riding around the West Village, Greenwich Village, soho East, anywhere kind of lower Manhattan. Right now I'm staying away from the Central Park Midtown. You know, sometimes some, some of the ladies who get in the cab love a finance bro. And I'm like, let's pop up to midtown. But I've had a few. The Petty, the real pedicab guys.

[B]

Oh yeah.

[A]

They don't like they're territorial because they're territorial and you know, my ride is free.

[B]

Yeah, it's like the jets and the Sharks.

[A]

So I got it exactly. I gotta, you know, they crawled so I could know run so I got a. So I could roll. They crawled so I could roll. So I need to respect their boundaries. So we're keeping it to downtown right now.

[B]

All right. Well, Walker, it is a pleasure meeting you so much. Date at so thank you so much. So thank you for this. Cheers to you.

[A]

Cheers.

[B]

And the success.

[A]

Cheers. Cheers. We love, love.

[B]

Hallelujah. This has been Kennedy saves the world along with Walker Ward. I'm Kennedy Listen ad free with a Fox News podcast plus subscription on Apple podcasts and Amazon prime. Members can listen to this show ad free on the Amazon music app. Oh, go ahead and leave me a review while you're there. I'd love to hear what you have to say. You've been listening to Kennedy saves the World on the Fox News podcast network.

[A]

Hey, I'm Trey Gowdy, host of the Trey Gaddy podcast. I hope you will join me every Tuesday and Thursday as we navigate life together and hopefully find ourselves a little bit better on the other side. Listen and follow now at foxnewspodcast. Com.