Kat on the Loose — "WINGMAN OF THE YEAR DATING SHOW" (May 1, 2024)

Host: Kat Zammuto
Guest: Hunter Werner (Creator/Host, “Wingman of the Year”)

Episode Overview

This lively, unscripted episode takes listeners onto the rainy streets of Manhattan with Kat and her guest, Hunter Werner, the creator of “Wingman of the Year”—a fast-growing digital dating show brand. Together, they chat about dating culture, Hunter’s creative process, relationships, modern romance, and the often chaotic world of dating apps, all while exploring the city organically, true to the spirit of both Kat’s and Hunter’s content.

Key Discussion Points & Insights

1. Origins & Concept of “Wingman of the Year” (06:16–14:42)

• Hunter describes his brand:

  • A digital media company creating dating show content centered around the idea of being a great “wingman”—not just in dating, but in life and friendship.
  • “It was built on the pillars of friendship. [...] Being a wingman means to be a good person, to be a good friend." (Hunter, 14:02)

• Format:

  • Main show is a live, interactive dating event, where contestants are introduced by their own “wingman” (can be friend, family, etc.).
  • Spinoffs include “Hot Date,” a tongue-in-cheek spin on “Hot Ones” where blind dating participants eat scorching chicken wings and answer tough questions.

• Viral Success

  • “Some of his videos on social media are getting millions of views. [...] I saw one of your videos on Instagram, you got like 7 million views!” (Kat, 14:42)
  • Plans to invite Miss New England as a “bachelorette” on a future live show (exclusive tease, 09:00).

2. Dating Culture, Social Media, and the “Choice Overload” Problem (15:16–17:52)

• Hunter's take:
  • Contests attract people mostly in their mid-20s to 30s, many still figuring out what they want out of dating.
  • “Dating is an absolute mess right now.” (Hunter, 15:57)
  • The abundance of dating apps and options leads to “situationships” and less sticking power in relationships.
    • “There's too many options down to that. [...] If you get in a fight with someone, it's just, 'Okay, bye, I’m going to go find somebody else.'” (Hunter, 16:35)
• Kat's perspective:
  • Apps allow encounters that wouldn’t otherwise happen, but create a “culture of people just order each other, like DoorDash.” (Kat, 17:18)

3. Hunter’s Approach: Bonding Through Shared Experience and “Uncomfortable” Dates (17:53–18:45)

• Shows like “Hot Date” put two people in the same uncomfortable situation to create quick camaraderie.
• “Growth happens when you’re uncomfortable. Do you agree?” (Hunter, 17:52)
  • “One million percent.” (Kat, 17:53)
• Kat and sidekick Karen agree that eating messy chicken wings isn’t their ideal first date, highlighting gendered expectations in dating.

4. Exploring Exclusive Relationships and “Situationships” (19:05–21:39, 58:02–61:22)

• Kat grills Hunter about his status:
  • He’s seeing someone exclusively but not "boyfriend/girlfriend" with her—she’s 23, he’s 29.
  • “When you say you’re exclusive, doesn’t that make you boyfriend-girlfriend?” (Kat, 19:24)
  • “No, not in this world, no.” (Hunter, 19:34)
• Explains there’s a bigger “commitment threshold” at the boyfriend/girlfriend level (meeting parents, birthdays, etc.).
• Later, they revisit the definitions: There’s a spectrum between casual dating, situationships, exclusivity, and formal relationships.

5. Geography and Dating: Is It “Easier” in LA or NYC? (22:03–26:11)

• Kat posits that good/bad dating experiences are universal and not city-specific, recalls an analogy: “You don’t go to the market for the rotten peaches, you go for the shiny mangoes.”
• Hunter observes: NYC women, in his experience, are “tougher to impress or obtain”—he says there might be a "geography effect," but it blends with cultural attitudes and options.

6. Men, Women, and Modern Romance: Options, Insecurity, and Marketing Yourself (31:15–35:21)

• Men’s fear of rejection: “Most men are very shy approaching women.” (Kat, 31:15)
  • “It’s part of the game though.” (Hunter, 31:18)
• Hunter’s “10/90 Rule”: “10% of the guys are dating 90% of the women.” (Hunter, 32:19)
  • Kat agrees women want “the top of the top,” leading to heavy competition and disaffected men.
• Dating is marketing: “You need to market yourself. It’s literally just effort. And I think that’s lost nowadays.” (Hunter, 34:59)

7. Practical Dating Tips and Philosophy (38:16–39:56)

• Get off the couch and into real life—meeting people face-to-face is irreplaceable.
• “Another great dating tip is to have no expectations.” (Hunter, 39:11)
  • Kat: “That’s why I never get nervous on dates. I don’t have an expectation, like, ‘oh my God, am I going to fall in love with this guy?’ It’s just a new experience.” (39:54)

8. Winging It—The Kat & Hunter Podcast Philosophy (29:04–30:28)

• Both value in-person, unscripted conversations.
  • “It's more like a reality, like, podcast.” (Hunter, 30:22)
  • “We just wing it.” (Kat, 30:31)
• Kat emphasizes organic, unedited content over studio polish.

9. Applications, Hope, and the Philosophy of Spreading Love (36:19–37:55, 62:23–63:11)

• To participate in the show, apply at wingmanoftheyear.com.
• Hunter’s mission: “I want to be the cupid of my generation. I want to impact the population. I hooked up so many people.” (36:49)
• Kat: Never give up on love. “Pick up the pieces, pull yourself by the bootstraps, [...] you should never give up on love.” (63:00)

10. Exes, Jealousy, and Trust in Modern Relationships (47:12–56:10)

• Kat discusses her friendship with her ex, Adam, who’s pet-sitting for her in LA.
• Hunter’s honest reaction: “If I was dating a girl and her ex pet-sat her dog—absolutely not. Red flag.” (48:45)
• Kat sees the value in post-breakup friendships, but knows it’s unusual.
• They debate trust, boundaries, and transparency:
  • “You got to trust each other.” (Hunter, 54:28)
  • Kat’s “credit card” analogy for trust: “I give you a small credit card, like let’s say with a thousand dollar credit limit, and then I give you more and more as I think that’s deserved.” (55:14)

11. Jealousy: The Spice of Relationships? (56:23–57:19)

• Both agree a little jealousy shows investment and can be healthy.
  • “I think a little bit of jealousy, a little spice.” (Hunter, 57:05)
  • “It means they like you. It means they care.” (Kat, 57:07)

12. Effort and Confidence as Keys to Dating (57:10–57:19)

• Relationships require effort and a dash of jealousy keeps things exciting.

Notable Quotes & Memorable Moments

• Defining a wingman:

  “Being a wingman means to be a good person. And to be a good friend, more importantly. So being a wingman doesn’t have to be dating. You know, it could be like holding the umbrella or opening the door for you.”
  — Hunter (14:02)

• On dating apps and endless choices:

  “People just order each other, like DoorDash, like food, you know? Pretty much yes, no, yes, no.”
  — Kat (17:18)

• About exclusivity vs. relationships:

  “When you say you’re exclusive, doesn’t that make you boyfriend and girlfriend?”
  — Kat (19:24)
  “No, not in this world, no.”
  — Hunter (19:34)

• On apps and marketing yourself:

  “Dating is marketing. Whether you’re a guy or a girl, you need to market yourself.”
  — Hunter (33:34)

• What men should do:

  “You need to sweep her off her feet. She wants to be won over.”
  — Hunter (35:21)

• Kat’s trust test:

  “You got to treat the person that you just met like a credit card. [...] I give you a small credit card, like let’s say with a thousand dollar credit limit. And then I give you more and more and more as I think that’s deserved.”
  — Kat (55:14)

• On never giving up:

  “Everybody deserves love. [...] When in doubt, get a wingman. Have somebody hype you up.”
  — Hunter (62:23, 62:41)
  “Pick up the pieces, pull yourself by the bootstraps, [...] you should never give up on love.”
  — Kat (63:00)

• Laugh-out-loud moment:

  “I want them to miss me forever and ever and ever. [...] I want them to be like, 'Oh my God, why did I give up Kat? She's the last Coca Cola Zero of the desert with ice under an umbrella.'”
  — Kat (51:00)

Timestamps for Important Segments

• Introducing Hunter & Show Concept: 05:33–09:56
• Wingman Format & Miss New England Tease: 09:00–09:24
• Viral Content & Brand Philosophy: 14:42–15:16
• Modern Dating: Challenges & Apps: 15:16–17:52
• “Hot Date” & Parody Premise: 10:22–11:28
• Exclusive Relationships vs. Situationships: 19:05–21:39
• Dating Geography—NYC vs. LA: 22:03–26:11
• Men, Women, and “Choice Overload”: 31:15–35:21
• Trust, Jealousy, and Exes: 47:01–56:10
• Applying for the Show: 36:19–37:55
• Final Reflections—Love & Resilience: 62:00–63:23

Final Thoughts

The episode brings an infectiously candid, fun take on the awkward thrills of dating in the digital age.
Hunter’s “Wingman of the Year” ethos merges old-school friendship with modern matchmaking, while Kat’s free-spirited hosting unleashes a whirlwind of stories, humor, and realness about love, heartbreak, exclusivity, and hope.

“Be open-minded and just have a conversation. [...] At least you got the experience. You put yourself out there, and they always walk away with at least a little more confidence.”
— Hunter (37:55)

For anyone navigating dating’s choppy waters (or thinking of putting themselves out there again), this episode is relatable, energetic, and deeply human.

Where to find more:

• Wingman of the Year — for participating/applying
• Kat on the Loose Podcast on YouTube
• Instagram: @wingmanoftheyear, @katontheloose

Video version available on YouTube for an even more immersive, “on the loose” experience!