Episode Overview

Theme:
In this episode, dating coach Connell Barrett helps listeners navigate the minefield of embarrassing dating mistakes—especially accidental, cringe-inducing messages or photos sent in the heat of the moment. Connell emphasizes that authenticity and recovery—rather than perfection—are what really make or break romantic connections. He answers three listener questions about recovering from a mortifying voice note, the dos and don’ts of sexting, and the right time to ask for a date on dating apps.

Key Discussion Points & Insights

1. Main Question: "Vexed by Voice Note"

Listener Dilemma:
A listener sent a flirty audio message about his date’s boobs (intended for a friend) to the woman herself. He asks: Is there any way to recover and get a second date?

Connell’s Core Message:

• It's about the recovery, not the mistake. Women notice how you handle mishaps, not the mishap itself (00:01).
• The mistake wasn’t vulgar—just “dorky, almost innocent” (Nom nom nom like a toddler).
• Women expect men to be attracted to them; the problem is objectifying. Expressing sexual interest is human, but avoid reducing a woman to her body parts (07:20).

Connell’s Recovery Plan:

• Step 1: Remember Recovery Matters Most
  • “When you make a mistake on a date, it's not so much the mistake, but how you bounce back from it that women are going to notice.” (00:02)
• Step 2: Own It with Humor, Then Shut Up
  • Send a self-effacing, lighthearted message that addresses the mistake, adds an apology, and mentions you like her for more than just her body:

    “Well, that was meant for my trainer, not for you. I am embarrassed. I am sorry for the screw up. Yes, I’m attracted to you, but I also know there is much more to you than just your body. So I hope you’re still up for Date number two. And I promise, no more voice memos of me making baby talk.” (13:00)

• Step 3: Cheer Up—It Might Help
  • Sometimes, mistakes can make you more attractive if you own them authentically. It shows you’re genuinely interested and not playing games (15:00).
  • “Be perfectly imperfect, or at least allow yourself to be perfectly imperfect.” (16:30)

Notable Story: Connell’s Sushi Date Fail

• He sat in the wrong booth with the wrong blonde, embarrassing himself but accidentally delighting his real date with his vulnerability.

  “You're as smooth as sandpaper,” [his date] said, laughing.
  “That actually made me want you. That was when I really wanted you.” (04:40–06:00)

• Lesson: The way you recover from a flub can create powerful attraction.

Notable Story: Oranges at Whole Foods

• Connell fumbled a “perfect opener,” knocked over an orange pyramid, and made his date laugh. His clumsy recovery and honest handling of the moment made the woman interested in him.
• “Yep, I’m that cool guy at Whole Foods, right?” (17:30)
• Lesson: Perfection is less attractive than authenticity and handling awkwardness with charm.

2. Sexting and Photo Exchange: “Digitally Confused”

Listener Dilemma:
David sent a shirtless, nipple-baring selfie after a woman sent flirty pics and requested “something sexy.” She ghosted him. Where did he go wrong? How to sext without it getting weird?

Connell’s Sexting Rules:

• If it looks like something for your dermatologist, don’t send it.

  “A woman’s nipple is a beautiful thing...A man’s nipple is unappealing...Her nipple is Michelangelo, yours is MySpace.” (29:00)

Three Dos:

1. Use Words, Not Body Parts
   • Sexual tension is created best with flirty language and vivid imagination.

   “Sexting works best when it’s about what you say, not what you show.” (30:00)

2. Keep Photos Natural
   • If you send pics, make them casual, confident, G-rated (smile, well-fitted shirt, nothing explicit).
   • No isolated body parts or “anatomical diagrams.”
3. Keep it Mutual and Consensual
   • Check in as things escalate. Ask if she’s into it before you proceed. If energy isn’t matched, pull back.

The Ultimate Don’t:

• “Don’t send anything that you wouldn’t want your mom to see, okay? Unless you’re certain that she wants it. By she, I mean your crush, not your mom.” (34:50)

Pro Tip:
If unclear on what “sexy” means for her, just ask!

“What kind of sexy do you want to see or hear from me?” (38:00)

3. How Many Messages Before Asking for a Date?

Listener Dilemma:
Chris is worried about double/triple texting and wants to know: How many messages should he send before proposing a date?

Connell’s Bottom Line:

• Text count is irrelevant; it’s about the value your profile communicates.
  • “Women don’t care how often you text. They care how much you bring to their love life and they gauge that...through your profile, your photos, your bio.” (43:00)
• Example of client Ben: He succeeded once his photos and profile reflected his authentic, appealing self—NOT because of a texting formula. (46:00)

Guidelines:

• Don’t count messages—count conversation threads (topics). Two is usually plenty.

  “Don’t count texts, count conversation threads. If you’re going to count anything, notice the cadence back and forth.” (54:00)

• Look for a roughly even texting balance (about 50/50).
• When in doubt, ask her out after one or two back-and-forths, if the vibe is good.
• Better to ask too soon than to stall and let interest fade.

Memorable Analogies:

• If you matched with Ana de Armas and she texted you three times, would you find her needy? Of course not. Desire outweighs arbitrary rules. (48:10)
• “Don’t count text messages. Read the room, count conversation threads… Notice the cadence back and forth.” (54:00)

Notable Quotes & Memorable Moments

• "Sometimes a goof turns into a gift." – Connell (01:40)
• “You sounded less like a creep and more like Cookie Monster let loose in a bakery.” – Connell, on dorky voice notes (09:25)
• “Be perfectly imperfect.” – Connell (16:45)
• “If the photo looks like something you would send your dermatologist, don’t send it to a woman.” – Connell, to ‘Digitally Confused’ (29:00)
• “Don’t send any isolated body parts, especially your junk, but also your nipple.” – Connell (34:13)

Timestamps for Key Segments

• 00:01 – Introduction and Listener Question: "Vexed by Voice Note"
• 04:40–06:00 – Sushi Date Story & Recovery Lesson
• 13:00 – Suggested Apology/Recovery Message
• 15:00 – Why Owning Mistakes Can Help Attract
• 17:30 – Oranges at Whole Foods Story
• 29:00 – “Digitally Confused” Sexting Advice
• 34:50 – Sexting Don’ts & Consent
• 43:00 – "How Many Messages Before a Date?" and Profile vs Text Focus
• 48:10 – Ana de Armas Analogy—Desire Beats Rules
• 54:00 – How to Gauge When to Ask for a Date

Takeaway Lessons

• Dating success comes not from perfection but from authentic, confident recovery from mistakes.
• Don't sweat embarrassing moments—own them with humor and honesty.
• Sext with words, not risky photos, and always make it a mutual, consensual exchange.
• Focus on your profile and energy, not arbitrary texting quotas.

For those struggling with dating confidence, Connell advocates for "radical authenticity" and offers practical, personable strategies for real-world romance without gimmicks.