Podcast Summary: How a Shy, Lonely Software Engineer Learned to Flirt and Found his Dream Woman—and How You Can, Too!

Podcast: How to Get a Girlfriend with Connell Barrett
Host: Connell Barrett
Guest: Tony (former client, software engineer)
Release Date: October 28, 2025

Episode Overview

This episode centers around Tony, a shy, mid-50s software engineer who recently found his dream woman after many years of struggle and self-doubt in the dating world. Host Connell Barrett and Tony explore Tony’s evolution from loneliness and insecurity, through practical exercises and mindset shifts, to the fulfilling relationship he has today. The episode is genuine, encouraging, and packed with practical advice—emphasizing authentic self-presentation and playful, unique approaches to flirting.

Key Discussion Points & Insights

1. Tony’s Background and Early Struggles in Dating

[01:18 – 05:09]

• Tony discusses his lack of dating experience, a long 17-year marriage, and the anxieties he faced reentering the dating world.
• Main issues included:
  • Low self-confidence and body image concerns
  • Feeling unworthy and fearing women wouldn't be interested in him due to his background and lack of experience
  • Anxiety about not knowing “how to flirt” or what women wanted

Notable Quote:

“I felt like there was something that I just didn't have or that women wanted, that I didn't even know about. And it just made me very nervous when I talked to women...” — Tony [00:00]

2. The Power of Challenging Negative Self-Beliefs

[05:42 – 08:22]

• Tony and Connell describe an “aha moment” when Tony logically evaluated the beliefs stopping him from dating with confidence.
• They did an exercise (“the awesome list,” minimum 25 reasons why Tony is a catch) to build self-belief.

Notable Quote:

“When we went through that exercise... I just realized there wasn't the data to really support these beliefs I had around why women didn't want me.” — Tony [06:06]
“...when you're able to name something, it all of a sudden becomes something you're able to overcome.” — Tony [07:22]

3. Embracing and Showcasing Authenticity

[08:22 – 10:28]

• They discuss the importance of bringing authentic interests and personality to both dating apps and real-life encounters.
• Tony’s reasons for being a great catch: musician, active (skiing, hiking, sailing), and more.

Notable Quote:

“I’m a very active person... I love to go skiing... I love hiking... I even got my sail certification.” — Tony [09:02]
“Let’s market ourselves, but in a genuine, real way.” — Connell [22:58]

4. The Playful Approach to Flirting

[10:28 – 15:37]

• Connell introduces the “Back to the Future” opener, a playful dating app message, which Tony successfully adapts for his now-girlfriend, Jennifer.
• The focus moves from logical/boring openers to fun, unique, playful banter that stands out.

Notable Quote:

“The premise of what you’re asking her is playful and it lets her be playful... I actually used it a lot because I really liked that. So much better than just asking someone how their day is going” — Tony [13:15]
“Flirting, in a word, is about play.” — Connell [15:37]

5. Tony’s Game-Changing First Date

[16:35 – 21:55]

• Tony describes a dramatically different mindset on his first date with Jennifer:
  • Relaxed, present, and unconcerned about “needing” her to like him
  • Allowed himself to be authentic, which led to a genuine connection
  • The encounter included hand-holding on the beach, shared musical enjoyment, and a memorable first kiss

Notable Quotes:

“I was relaxed and having fun... I didn’t have this sense of panic... that my future happiness depended on her liking me.” — Tony [17:20]
“She really likes the real Tony.” — Tony [17:58]
“We walked with our fingers entwined on the beach... that moment definitely took some courage.” — Tony [20:08]

6. Concrete Changes: Profile Authenticity & Confidence

[22:29 – 23:26]

• Tony updated his dating profile to feature authentic images of his real interests (e.g., playing guitar, boating).
• This made his profile stand out to women genuinely interested in the real him.

7. Lasting Transformation and Relationship Happiness

[23:26 – 25:54]

• Tony details how happy he is with Jennifer and how different this relationship feels compared to his past.
• He emphasizes shared values, interests, and the feeling of not “settling.”

Notable Quote:

“With Jennifer, I feel like I’m not settling for anything... we connect on so many different levels... it’s been so incredible.” — Tony [24:10]

8. Final Advice for Other Introverted Men

[26:29 – 27:45]

• Tony offers hope and motivation: there are “an abundance of women out there that are into a guy like you.”
• Disputes the rom-com notion that it’s “impossible” to find real love.

Notable Quote:

“It is possible to find that for yourself.” — Tony [27:35]

Memorable Moments & Quotes (with Timecodes)

• “The Fonz” vs. “Richie Cunningham” Insightful Banter:
  Connell: “It’s ironic you thought you had to be Fonzie and I look a little bit like Richie Cunningham.” — [05:09]
• Tony’s Adaptation of the Back to the Future Opener:
  Tony: “I modified it a little bit because... she was more of a boba person... ‘Did we get ice cream or boba?’ And she actually responded, ‘You can get them both... it’s called a boba float.’” — [13:07]
• The First Date on the Beach:
  Tony: “We walked with our fingers entwined on the beach... standing there listening to the music, she just leaned her head on my shoulder, so I put my arm around her...” — [21:00]
• Connell’s Closing Reminder:
  Connell: “Your dream girlfriend is out there, but she’s gonna have to meet the real authentic you.” — [27:55]

Timestamps for Important Segments

• Tony introduces his past struggles and fears: [01:18 – 05:09]
• Connell & Tony discuss mindset shift and self-worth exercises: [05:42 – 08:22]
• Building and sharing the “awesome list”: [08:22 – 09:50]
• Illustration of the playful “time traveler” opener: [11:41 – 13:32]
• Tony on how playful openers led to meeting Jennifer: [13:07 – 15:37]
• Description of their first date, gestures of attraction: [16:35 – 22:12]
• Profile authenticity and post-date reflections: [22:29 – 23:26]
• Tony’s happiness and how the relationship differs now: [23:26 – 25:54]
• Tony’s advice to introverts and those doubting themselves: [26:29 – 27:45]

Takeaways for Listeners

• Identify and challenge your negative dating beliefs—use data and logic if that fits your thinking style.
• Create a personal “awesome list” to build confidence in your value as a partner.
• Lead with authenticity—show your real hobbies and passions in your profile and in person.
• Break the ice with playful, creative openers that set a fun tone from the start.
• Stay present and relaxed on dates, focusing on being yourself rather than trying to “win” someone’s approval.
• It is possible—at any age, and even with past struggles—to find a meaningful, authentic relationship.

Episode Tone

Warm, witty, insightful, and practical—encouraging listeners to trust that their authentic selves are enough to find love, and providing concrete steps to get there.