From Playdates to First Dates: The Single Dad’s Dating Reset (Live Coaching with Zach!)

Tue Sep 30 2025

Online dating is tough for most men. But when you’re a single dad, it’s hard to find the energy and motivation. In this live coaching session, dating coach and bestselling author Connell Barrett helps his client Zach—a single dad re-entering the...

Transcript

A (0:00)

That's kind of awesome and douchey, what you just did. And then she gives me her number. Welcome back to another episode of how to Get a Girlfriend. I'm your dating coach, Connell Barrett. Think of me as your podcast guru, here to help you get get better on the dating apps, get more matches, flirt with women, and get a great girlfriend. And do it by being authentic. No sketchy pickup artist moves needed. And today I have a returning client for the first time ever, a two timer. Welcome back to the podcast, Zach. Welcome, bro.

B (0:46)

Thank you. I don't know if that's good or bad. Since I'm back, it means I still need help. If I were doing better, I wouldn't need to be here and I would be a one timer.

A (0:57)

You're doing great. Just for context. So, Zach, you were here many months ago as a single dad. You are getting back into the dating game, and you're back on the apps, and you're slowly but surely getting back into going out to meet some women. And you're also my personal trainer. So if for you, for those of you who are watching this video on Spotify, where there is video, you're seeing, I have rippling huge muscles. It's clearly because of this man.

B (1:25)

So anyway, you have a 10 pack. You have a 10 pack at this point, right?

A (1:31)

Oh, I feel like I have a 2 liter, not a 6 pack. At least some days when I eat too much. But no, you got me looking good. Anyway, so, yeah, let's just get to it. I know we were doing a little chat before we hit record today, and you were talking about some issues with the dating apps, some mindset stuff, and just some questions about the dating profile. So let's just make this a no holds barred question and answer. You're a Single dad, late 30s.

B (1:56)

Is that right? 40 coming. 41. I don't know how it happened.

A (2:01)

I'm sorry, I thought you were. Okay, 41. Okay. So early 40s.

B (2:04)

40, not 41.

A (2:06)

Sorry. That's right. 40 is not early 40s.

B (2:10)

It's actually not counting or anything, but, yeah, for sure.

A (2:13)

Cool. Well, yeah. So you're a good guy looking to get back out there, and you're on the apps. Where would you like to start? What are you frustrated with? What isn't working? What can I help you with?

Summary

Podcast Summary:

How to Get a Girlfriend with Connell Barrett
Title: From Playdates to First Dates: The Single Dad’s Dating Reset (Live Coaching with Zach!)
Release Date: September 30, 2025

Overview

In this episode, dating coach Connell Barrett welcomes back his client Zach—a single dad, personal trainer, and returning guest—for a live coaching session. The central theme: navigating the dating world as a busy single father in his 40s, with a focus on authentic self-presentation, mindset shifts, and practical strategies for using dating apps, making time for romance, and confidently moving from online conversation to real-life dates.

The discussion is candid and full of practical insights, exploring the obstacles single parents face, profile optimization, how to stand out honestly online, and how to advance conversations to real-life connection—all while staying true to oneself.

Key Discussion Points & Insights

1. Zach’s Progress and Current Challenges

[01:56 - 03:30]

Zach shares that since his last appearance, he’s invested more time in dating apps and is seeing better matches and engagement.
He acknowledges guidance from Connell as transformative:

“A lot of the guidance you’ve given me has really helped get me to where I am...which is away from where I was.” (03:15, Zach)
Despite anxiety about approaching women in real life, his experiences have gone better than expected.

2. Dating Profile Audit: Honesty, Specificity, and Humor

[04:01 - 20:44]

Photos:

Zach updated his main dating profile photo to a professional but friendly headshot, which notably increased matches.
Connell's advice: A solid, authentic photo with a real smile and natural backdrop works wonders.

Prompts:

Zach’s standout prompt: “I’m a total DILF. (Dedicated, Invested, and Loving Father…)” works well, landing as cheeky but sincere.

“...it was like, hey, I have a son and this is my homeboy...I take care of my family responsibilities...” (16:45, Zach)
Connell points out the importance of specificity and storytelling in prompts rather than generic qualities:

“If you write something that’s going for the universal, you don’t get anything. But if you go for something specific, you’ll get the universal.” (08:39, Connell)

Profile Tone:

Zach and Connell discuss how the profile must align with what Zach truly wants—currently, fun, chemistry, and honest connection (possibly casual, not searching for a life partner at the moment).
Practical advice:

“We want her to feel like, oh, he’s talking about me and I want the same thing.” (14:28, Connell)
Action: Revise prompts to paint a vivid, playful picture (e.g., rooftop margaritas, Porsches, and espressos).

3. Communicating Expectations and Time Constraints

[24:41 - 40:49]

As a single dad, Zach struggles with scheduling and fears mismatching expectations—especially with younger women with different time availability.
Connell’s advice: Be forthright but not apologetic. Offer realistic options upfront:

“Give her your schedule first...Even though the choice is limited because you’re busy.” (26:23, Connell)
Don't over-explain or offer too much detail early; keep it light and focused on making plans.

4. Handling Fumbled Connections and Ghosting

[27:48 - 40:49]

Zach recounts missing out on a match due to busy weeks, delayed texts, and feeling he “fumbled at the goal line.”
Connell shares playful tactics to revive icy conversations (“back from the dead” texts):

“I just feel like we’re growing apart, baby. We don’t talk anymore…” (31:02, Connell)
Main lesson: Act quickly while the “iron is hot” and always drive towards a concrete plan—don’t get bogged down in over-explanation.

5. Mindset Reset: Commitment and Taking Action

[41:39 - 45:43]

Connell delivers some tough love, urging Zach to fully commit to making dating a real-life priority—not just a digital pastime:

“Burn the boats...Decide that you’re going on a date next Friday...Treat it like this has to happen.” (41:39, Connell)
Zach realizes his half-in, half-out approach is limiting him and commits to making time and following through.

“I didn’t even realize how half in, half out, and how, like, lukewarm I’ve been...” (42:35, Zach)

6. Advanced Coaching: Flirting, Banter, and Radical Authenticity

[46:13 - 66:28]

The Four Flirting Frequencies:

Banter (playful teasing)
Clear romantic/sexual statements of intent
Emotional connection and vulnerability
Non-verbal/physical flirtation

How/When to Switch Gears:

Default to your strengths but recognize when banter is stalling (especially with women who don’t engage the same way).
When appropriate, make clear, honest, non-boilerplate statements of attraction—just “put it out there” without worrying about being smooth.

“You just do it. You just make a decision in your mind to go, okay, it’s time to say something clear and specific.” (52:28, Connell)

Radical Authenticity:

Connell encourages saying exactly what you’re thinking/feeling (unless it’s truly inappropriate), as it’s respected and cuts through the noise:

“What I’m thinking and feeling is what I’m saying and doing...just speak the deepest truth.” (57:20, Connell)
Telling anecdotes of both brilliant and awkward honest moments (e.g., asking for a number while on a failing date), Connell demonstrates that realness is often preferable over slick lines.

Memorable Example:

“That’s kind of awesome and douchey, what you just did. And then she gives me her number.” (65:09, Connell, recounting a time he asked another woman out during a bad date, and the honesty worked)

7. Concrete Commitments and Closing

[67:31 - 70:26]

Connell insists on ending with actionable commitments:
Zach commits to clearing his Friday for a real date or attending “Fearless Friday” (Connell’s live group outing and approach night).

“That I can 100% commit to. That’s committed.” (69:18, Zach)
Action, not further theorizing, is the final prescription.

Notable Quotes & Moments

On authenticity in online profiles:

“I like that one because that’s very you. Authentic. It’s cheeky, it’s funny, but it’s also conveying something important.” (17:23, Connell referring to Zach’s “DILF” prompt)
On radical honesty:

“What I’m thinking and feeling is what I’m saying and doing…just speak the deepest truth.” (57:20, Connell)
On commitment:

“Burn the boats. Decide that you’re going on a date next Friday. Treat it like this has to happen.” (41:39, Connell)
On recovering cold leads:

“I just feel like we’re growing apart, baby. We don’t talk anymore. We haven’t made sweet, sweet love in ages...Should we try one more time to make romance happen?” (31:02, Connell’s “back from the dead” text)
On self-awareness:

“I didn’t even realize how half in, half out, and how, like, lukewarm I’ve been…” (42:35, Zach)
On the power of a playful, honest nudge:

“That’s kind of awesome and douchey, what you just did. And then she gives me her number.” (65:09, Connell)

Timestamps for Key Segments

Zach’s progress & challenges: 01:56 – 03:30
Profile photo & prompt coaching: 04:01 – 20:44
Clarifying dating goals & writing for your audience: 10:06 – 17:41
Communicating constraints & planning dates: 24:41 – 27:07
Fumbling, ghosting, and playful recovery: 27:48 – 33:44
Connell’s “burn the boats” call to action: 41:39 – 45:43
Directness & “radical authenticity” in flirtation: 46:13 – 66:28
Commitments & closing: 67:31 – 71:10

Conclusion

This lively, insightful episode delivers to anyone seeking to date authentically—especially single parents—the message that results stem from intentional action, specificity, and realness. Connell and Zach blend practical, granular advice with big-picture mindset shifts, always returning to the foundation: radical authenticity, boldness, and moving forward—one real connection at a time.