Kat on the Loose: INSIDE THE MIND OF SINGLE GUYS

Host: Kat Zammuto
Guests: Michael Patrick Shields & Michael “Henderson” Henderson
Date: November 26, 2025

Episode Overview

In this candid and playful episode, Kat Zammuto welcomes two of her single male friends—Michael Patrick Shields, a veteran radio host and travel writer, and Henderson, a successful entrepreneur with a law enforcement and private security background—to share an unfiltered look into the mind of single men. The conversation covers a range of relationship topics: why these high-value men are single, their dating philosophies, red flags, being approached by women, boundaries, and the dynamics of success in relationships—all seasoned by anecdotes, laughter, and a dash of advice for women seeking insight into male perspectives.

Key Discussion Points & Insights

1. Meet the Guests & Setting the Scene

• Kat introduces Michael Patrick Shields and Henderson, both highly accomplished, attractive, and single—sparking curiosity about why they’re still unattached.
• Henderson appears via the warmth of his fireplace; Michael Patrick, ever the showman, records from his bedroom, “candles over here and champagne. So I welcome you to my bachelor bed” ([01:58]).
• The group reminisces about a recent night out, noting how organic conversations about dating challenges inspired this episode.

2. Why Are They Single? (05:00–09:00)

• Henderson: Never married, claims he’s been proposed to four times but didn't accept due to his hectic, travel-centric job and inability to offer consistency to potential partners.
  • “My job was traveling all over the world and protecting people... I was gone maybe 200 days a year... That just wasn’t conducive to giving them the stability they wanted. So I said no.” ([05:47])
  • Comfortable alone, sometimes feels open to relationships but isn’t always seeking them enthusiastically.
• Michael Patrick: Four marriages, five engagements, but not “afraid to commit.”
  • “At least I'm not afraid to commit...I was head over heels with all of them and to some degree, to this day, I still am” ([08:10]).
  • Prefers relationships to happen organically rather than through relentless pursuit or the “dating app hustle.”

3. Dating in the App Era: Green Flags & Red Flags (09:00–16:45)

• Green flags for Henderson: Kindness, meeting in the real world—not on apps.
  • “Kindness as soon as I meet...I’ve been very fortunate to meet people just in person” ([09:28]).
  • Tried dating apps very briefly (“probably the worst time,” during pandemic lockdown). Not for him.
• Michael Patrick’s Foodie Call Experience: Cautious about dating apps after being used for meals.
  • “They call it a foodie call, not a booty call. You end up having this dinner...and then off they go” ([10:39]).
  • Both men agree high-value dating happens off the apps and with selectivity.
• Kat on Date Effort: Prefers a man who plans romantic, thoughtful dates.
  • “I love old-fashioned men. It has nothing to do with the money... I like the gesture of a guy that plans a romantic date. I want a type A man...” ([11:41]).

4. Paying for Dates & Reciprocity (19:08–20:55)

• Sex Early in Dating: Does it change their view of a woman?
  • Henderson: No, as long as she displays genuine reciprocation and kindness. What turns him off is lack of generosity in return—no small gestures or tokens.
    • “If we go somewhere and they have coconut water and you don’t want to buy me coconut water, then I’m probably going to be almost done with you...” ([20:05])
• Both men prize reciprocity in kindness, not entitlement or expectation.

5. Gold Diggers, Foodie Calls, and Boundaries (21:27–26:06)

• Henderson’s Gold Digger Story: At a Beverly Hills bar, he refuses to buy drinks for a group of women who expected it. He notes he does not attract those types.
  • “Those gold diggers don’t like me anyway, so I’m good.” ([22:52])
• Both men are wary of being used for financial gain, agree that gestures should be genuine, not transactional.
• Michael Patrick: Still enjoys classic chivalry—“the male thing kicks in where you feel gallant and maybe you feel generous...” ([26:06])
• They also highlight “mini-relationships”—meaningful spontaneous connections during travel.

6. Being Pursued vs. Pursuing (28:11–32:31)

• Kat: Never pursues men; believes men should be the hunters.
• Henderson: Likes to see interest from a woman but too much pursuit gets “annoying”—effort is appreciated, desperation is not.
  • “It can be annoying...if it’s too aggressive, too much, I’m like, what’s up with that?” ([31:06])
• Michael Patrick: Enjoys being pursued but with balance, values mutual effort.

7. Time Management & Relationship Priorities (33:12–35:26)

• “Too Busy” Excuse:
  • Kat challenges the “busy” narrative: “When you like someone, you can be the busiest person on the planet...you always fit that person in your schedule.” ([32:31])
  • Henderson: Agrees, but stresses that timing and seasonality matter—sometimes patience is needed.
  • Michael Patrick: When truly struck by “the thunderbolt,” nothing stands in the way.

8. Red Flags & Deal Breakers (39:00–45:39)

• Male Friends as a Deal Breaker:
  • Michael Patrick brings up if having mostly male friends is a red flag; Kat counters that trust and loyalty are non-negotiable—type A men aren’t threatened.
  • Henderson: Boundaries are the core issue; lack of them is a deal breaker.
    • “If you don’t have boundaries just in your life, period...that’s the biggest red flag in my life.” ([42:27])
• Michael Patrick: Warns that the spark-creating traits can aggravate you in the long term. Prefers a “flexible freeze”—be open to changing expectations.
  • “Sometimes the things that will attract you...maybe you can’t live with [them]” ([45:07]).

9. Are Men Intimidated by Successful Women? (46:25–49:07)

• Kat: Asserts most men are intimidated by highly successful women, despite what they say.
• Henderson: Personally unconcerned by a woman’s economic or career status—but only if she maintains femininity in the relationship. Admits, “I think most men...are [intimidated],” and they “can’t handle that.”
• Michael Patrick: Sees successful women as exciting and aspires to be with someone who “brings new intellect and excitement.”
  • “I aspire to be with women who can bring new intellect and new excitement...” ([47:49])

10. Sweet Gestures & Real Connection (50:14–53:13)

• Handwritten Notes & Small Gifts:
  • Michael Patrick shares a funny story about gifting a date a candle—swapping a $97 Ivy candle for a $15 Michaels store candle out of practicality ([51:02]).
  • Kat emphasizes how meaningful such gestures are for women.
• Both value genuine acts over grandiosity—a theme echoed throughout the episode.

Notable Quotes & Memorable Moments (with timestamps)

• On their relationship status:
  • “At least I'm not afraid to commit is what I tell them, you know...I was head over heels with all of them and to some degree, to this day, I still am...” – Michael Patrick Shields ([08:10])
• On first date expectations:
  • “I like the gesture of a guy that plans a romantic date. I want a type A man.” – Kat ([11:41])
• On food-dated dating apps:
  • “They call it a foodie call, not a booty call.” – Michael Patrick ([10:39])
• On reciprocity:
  • “If we go somewhere and they have coconut water and you don't want to buy me coconut water, then I’m probably going to be almost done with you, right?” – Henderson ([20:05])
• On boundaries:
  • “If you don't have boundaries just in your life, period... that's the biggest red flag in my life.” – Henderson ([42:27])
• On being too busy:
  • “When you like someone, you can be the busiest person on the planet...you always fit that person in your schedule.” – Kat ([32:31])
• On success in women:
  • “They say they want an independent woman, but then when they get one, they can’t handle that.” – Henderson ([47:45])
  • “I aspire to be with women who can bring new intellect and new excitement.” – Michael Patrick ([47:49])

Timestamps for Important Segments

• Introductions & Why Single? – [01:58] to [09:00]
• Green Flags/First Date Philosophy – [09:28] to [16:45]
• “Foodie Call” & Dating App Stories – [10:39] to [14:10]
• Reciprocity & Early Sex – [19:08] to [20:55]
• Experiences with Gold Diggers – [21:27] to [22:52]
• Being Approached, Chivalry – [26:06] to [27:32]
• Being Pursued Versus Pursuing – [28:11] to [32:31]
• Time and Attention in Relationships – [33:10] to [35:26]
• Red Flags & Deal Breakers – [39:00] to [45:39]
• Success in Women & Male Insecurity – [46:25] to [49:07]
• Sweet Gestures & Candle Story – [50:14] to [53:13]

Tone & Style

• The tone is lighthearted, irreverent, yet often deeply self-aware, alternating between playful banter and moments of genuine vulnerability.
• Kat serves as a strong, sassy moderator who is both empathetic and forthright. Henderson is reflective, analytical, and values authenticity. Michael Patrick brings wit, self-deprecation, and a seasoned perspective on relationships.

Key Takeaways

• High-quality single men do exist; they value kindness, selectivity, and real-world connection.
• Reciprocity and genuine gestures matter as much as (or more than) traditional gender roles or financial generosity.
• A major red flag for both is a lack of boundaries; confidence and mutual respect are non-negotiable.
• Most men are honest about being intimidated by truly independent, successful women, but the right partner finds this (paired with femininity) attractive.
• Both playful and profound, the conversation demystifies how successful single men approach love, dating, and relationships.

For more from Kat Zammuto and her guests, listen to the full episode of "Kat on the Loose" wherever you get your podcasts, or find the video episode on YouTube.