Vault: Single Girl Bootcamp

Summary

The Bert Show: Vault - Single Girl Bootcamp

Date: June 12, 2026
Main Guests: Deborah & Olivia (Authors of “FlirTexting”)
Main Theme: Navigating Dating in the Digital Age—Single Girl Bootcamp focuses on how social media, texting, and online presence are changing modern dating, with practical advice especially for single women getting back into (or just starting to navigate) the dating scene.

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Episode Overview

This episode of The Bert Show kicks off a week-long “Single Girl Bootcamp,” diving into the complexities of dating for singles in the age of constant digital connectivity. Bert and co-hosts welcome Deborah and Olivia, experts in digital flirtation and authors of “FlirTexting”, to share actionable “rules of thumb” for managing relationships via Facebook, texting, Twitter, and more. They explore social media’s effect on romance—discussing when to “friend” someone, how much online interaction is too much, and the delicate art of keeping things light, fun, and mysterious.

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Key Discussion Points & Insights

1. The Overwhelm of Social Media in Dating

[02:21] Jen/Wendy:

• Explains how social media has introduced a “really new element” into dating that many people feel unprepared for.
• Listeners often write to the show about confusion and challenges of digital romance.

[02:48] Olivia:

• Warns against “oversaturation” early on (i.e., constant communication through multiple channels), which can “burn out that love connection” and erode the essential “mystery” that fuels new relationships.

2. Guidelines for Online Interactions

[04:07] Olivia:

"You should refrain from being Facebook friends... until the fourth date. The first three dates, you’re kind of feeling that person out. I think by the fourth one, you can safely say you guys are dating."
[04:50] Deborah:

• If you’re already friends with a crush, don’t post anything on their wall—keep things private and avoid public displays, which can feel overwhelming or showy.

[05:18] Olivia:

“The biggest turnoff... is when a girl comments on every single status or picture or link that they put up. It reeks of trying too hard.”

3. Tone and Content: Keeping It Light

[06:00] Deborah:

• Texts and social media messages should “supplement” real relationships, not become the main form of connection.
• Keep topics fun—serious conversations are best reserved for real-life or phone calls.

[06:53] Jen/Wendy:

“You can’t express a serious emotion and then an emoticon to really get across. So... it should just be fun and flirty and light.”

4. Responding to Flirty Messages: Take Your Time

[07:38] Deborah:

“You should stop.”

• Don’t be impulsive in replies.
  [07:41] Olivia:

“Just because it’s speedy technology doesn’t mean you need to be speedy with your response.”

5. Is Facebook a Legitimate Way to Meet?

[08:46] - [09:51] Discussion of a real story:

• A guy privately messages a girl after seeing her tagged at a party—she blocks him. The group debates if this is normal or an overreaction.

[09:10] Olivia:

“Absolutely, people are actively using [Facebook] almost as a dating site at this point. ...If you make it personal... that’s better for you.”

[10:00] Deborah:

• Warns that generic mass-messages are a turnoff; personalization is key to standing out.

6. Online Flirting and Infidelity

[10:55] Host:

• Is it okay to comment on other people’s photos after you’re exclusive?

[11:06] Deborah:

“Yeah, if you do it very lightly... if you don’t say anything inappropriate. Absolutely.”

[11:27] Olivia:

• Gives an anecdote of someone being obviously unfaithful online, despite publicly listed relationship status—citing this as “a huge weird thing.”

7. Chivalry and Technology

[12:06] Jen/Wendy:

• Asks if chivalry is dead in the digital age—how should a single woman balance tech with expecting “gentlemanly” behavior?

[12:32] Deborah:

“It’s about mixing it up... A guy that really likes you will call you at some point... but will use texting to flirt.”

[13:14] Olivia:

“Whether he Facebooks you and gets your phone number that way, like, it’s gotta come down to the phone call.”

8. First Impressions: Your Facebook Profile Matters

[13:45] Deborah:

“When a girl gets a guy’s number, the first thing she’s going to do, whether she’s friends with you or not, is check out your Facebook profile. So you have to make sure that picture is very, very wonderful and you’re not doing anything in it that she could disagree with.”

• Mentions their blog post: “25 Worst Things You Could Do in Your Facebook Profile Picture” ([14:19])

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Notable Quotes & Memorable Moments

• On digital “mystery”:
  “If you do saturate these communication lines early on... it’s just probably going to burn out that love connection really quickly because you’re just kind of so attainable and out there.” — Olivia [02:48]
• On Facebook friending etiquette:
  “Refrain from friending someone to like the fourth date... Just kind of hold out on that because, I mean, I think that’s the safest way to go about.” — Olivia [04:07]
• On personalizing messages:
  “If you want to make yourself stand out... If you make it personal that a girl knows you didn’t just copy and paste it, I think that’s better for you.” — Deborah [10:24]
• On supplementing, not replacing, real contact:
  “Texting and Facebooking... are ways to supplement a relationship that should also include phone calls and face to face, because that’s how you build a relationship.” — Deborah [06:00]
• On profile pics:
  “You have to make sure that that picture is very, very wonderful and you’re not doing anything in it that she could disagree with.” — Deborah [13:46]

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Important Timestamps

• 01:46: Episode theme introduced—Single Girl Bootcamp, digital/dating focus
• 02:21: Listener feedback on dating and social media
• 02:48: Olivia’s advice about mystery and oversharing
• 04:07: When to friend/date on Facebook
• 06:00: Importance of keeping digital communication light
• 07:38: Advice on pausing before replying to flirty messages
• 09:10: Is it okay to initiate on Facebook?
• 10:00: The problem with generic DMs
• 10:55: Digital boundaries and “cheating” online
• 12:06: Technology vs. chivalry
• 13:45: How your Facebook profile affects first impressions

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Final Takeaways

This episode provides practical, realistic advice for navigating the minefield of modern dating:

• Wait before friending—Don’t rush into digital intimacy post-first date.
• Keep your online interactions light, fun, and mysterious.
• Personalize all communication—don’t copy/paste.
• Balance digital communication with real calls and face time.
• Your online presence (especially profile pictures) matters.
• Chivalry isn’t dead—expect (and require) real-world connection.

Deborah and Olivia underscore that, despite all digital advances, true relationship-building still relies on genuine, real-world interactions. The main message: use technology to enhance, not dominate, your romantic connections.

---

Relevant Links:

• “FlirTexting” by Deborah and Olivia
• flirtexting.com: 25 Worst Facebook Profile Pic Mistakes (as mentioned)
• thebertshow.com

(All timestamps MM:SS from start of actual content—skipping advertisements.)

Transcript

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[Host/Interviewer]

Hey, is this Olivia or Deborah?

[Deborah]

This is Deborah.

[Host/Interviewer]

Hi, Deborah. How are you?

[Deborah]

I'm good. How are you?

[Host/Interviewer]

Hold on, we'll get Olivia on. Hi, Olivia, how are you?

[Olivia]

Hi.

[Host/Interviewer]

Welcome back. Welcome back to the show.

[Olivia]

Thank you. Good to be back.

[Host/Interviewer]

All right, Jen and Wendy are gonna spearhead this, but we're starting. You guys are kicking off this single goal boot camp that we're doing all week, and it's about helping single ladies and gentlemen navigate the dating waters. And the reason we have you guys joining us is because, you know, we originally talked to you in studio about texting, but questions have come up about Facebook commenting and tweeting and direct messages. And replies and so much more than texting. So that's why you guys, that's what you're representing, the social media aspect of dating.

[Jen or Wendy (Co-host or Guest)]

And we. We just get a ton of email from listeners. Anytime that Wendy and I talk about dating or being single, whenever we share it on the show, we get lots of responses from other women listening who are single or maybe newly single getting back out on the scene. And all the social media is this really new element to dating now that nobody's really navigated that before. So we were kind of wondering if you can give us, like, some rules of thumb, some definite things to always remember when you're on those sites.

[Deborah]

Right.

[Olivia]

I mean, I guess the biggest thing to remember is, you know, we never before were inundated with all these technologies and are kind of like. Like 247 coverage of our lives on Facebook. And people are tweeting now. I mean, there's just so much going on that I think everybody just needs to be mindful that if you do saturate these communication lines early on, and I'm talking, you know, you're emailing your BlackBerry messenger and you're Facebooking with, you know, your crush, that it's just probably going to burn out that love connection with really quickly because you're just kind of so attainable and out there, and everything about you is out there that you're kind of losing that mystery, which is the really the kind of thing that you want to keep, especially early on in the love connection.

[Host/Interviewer]

Is there, like, a guideline to go by? Because the texting and the tweeting can be somewhat private, but if you're going to Facebook message someone, like, comment on their wall and post something, that almost seems like it's a question that has to be or an issue that has to be addressed beforehand because people might not want to know who, you know, like, if I'm dating somebody, I might not want the whole world to know it just yet. If we've only been on one date, is there a guideline?

[Olivia]

Well, here's the rule that we always tell single girls is that you should refrain from being Facebook friends or, like, friending. Facebook friending someone to, like, the fourth date. I mean, let's face it, the first, you know, three dates are, you know, you kind of feeling that person out. I think by the fourth one, you can. You can safely say that you guys are dating and headed that on that road. So we tend to kind of hold back on whether the girl's Facebook friending him or whether he's Facebook Friending her. Just kind of hold out on that because, I mean, I think that's the safest way to go about.

[Deborah]

So what if you're already Facebook friends with your crush?

[Olivia]

Should we delete them or just avoid

[Deborah]

posting anything on their wall? Yeah, definitely avoid. You know, you don't want. It's. It's very. You don't want everybody to know what's going on. And like Olivia said, you want to keep the mystery, so. And guys also don't appreciate it when a girl that they just started to date posts on their Facebook page. Hey, I had a great time last night. Because early on, early on, that's. That's not a good move to make too.

[Olivia]

Clean, private thing. I mean, I think that's something that you can private message on Facebook and not make it public domain, you know? Right. The biggest turnoff to guys that we've gotten is that when a girl comments, like every single status or picture or link that they put up, I mean, it reeks of trying too hard. And it's just. It's like you don't want everybody knowing, you know, you. That you're out there and you have nothing better to do but to comment on his.

[Jen or Wendy (Co-host or Guest)]

Well, and two, don't you think it needs to be. The tone needs to be light and fun, like in any sort of text communication or social networking. Like, to me, it should stay light and fun. Any sort of serious subject matter. I feel like you should talk about.

[Deborah]

Oh, absolutely. No. Texting, Facebooking, BBMing. It's all supposed to be light and fun because we have found that a very big misconception that people have come across is that. That they think that now that texting is around, that you need to have all these conversations on texting. But that's actually absolutely incorrect. You know, texting and Facebooking and all those things are ways to supplement a relationship that should also include phone calls and face to face, because that's how you build a relationship. And all those other fun things in social media should be just that they should be fun and light.

[Jen or Wendy (Co-host or Guest)]

Exactly. Yeah. Because I think that that's a mistake that a lot of women make is they'll get serious or they'll, like, try to express their. Express their emotions in that way. And it's like, you can't really do that. You can't express a serious emotion and then an emoticon to really get across.

[Host/Interviewer]

Smiley face.

[Jen or Wendy (Co-host or Guest)]

Yeah. Smiley or a wink or a sad or whatever it is. So, like, really say what you. What you need to say. I think it should just be fun and flirty and light.

[Deborah]

Yeah, Light thing about flirting in these social media environments is that you're able to flirt in a controlled environment. You're able to actually think about what you want to say and how it's going to make you look before putting it out there. So if you're smart about it, then it could really, really help you out.

[Jen or Wendy (Co-host or Guest)]

And for Single Girl boot camp, what would be your suggestion before immediately replying to something you get from a boy? So say you get, like, a flirty text from a boy or a flirty direct message or whatever else it is. Like, do you have any advice on. Okay, before you reply, you should do what?

[Deborah]

You should stop.

[Olivia]

Stop and think. Well, what we usually say is that the first thing that pops into your mind is most likely impulsive and driven by emotion. So what you want to say initially is probably you're going to think of something better in an hour, you know, and, like, just hold off. There's no need. Just because it's speedy technology doesn't mean you need to be speedy with your response.

[Host/Interviewer]

Which is the rule that you applied to texting when we had you in.

[Jen or Wendy (Co-host or Guest)]

Exactly. It's the same kind of thing. Like, if you take your time, then you can be witty and light and funny.

[Host/Interviewer]

Now, we had a guy in studio, actually a friend of the Birch Show a couple months ago, and he approached a girl. He got invited to a party that he couldn't attend, but then was looking at the pictures of the party, and in those pictures found a girl that he thought was attractive. So checked out her Facebook page, and whatever he saw on her Facebook page, he's like, wow, this is, you know, this is a cool girl. So he sent her a message, not a public message, a private message on Facebook, and asked her if there was any, you know, if she's single and if she wouldn't mind grabbing a cup of coffee.

[Jen or Wendy (Co-host or Guest)]

And I thought his approach was kind of cute because he said, you know, I was supposed to go to the party where you went, and, you know, kind of. Man, I'm really mad I missed it because I missed the chance of meeting you.

[Host/Interviewer]

So the question is, is Facebook or any social media that has a picture attached, is that an acceptable medium for meeting? Yeah, for the initial meeting.

[Olivia]

I think people are using it. Absolutely. I think people are actively using it almost as a dating site at this point. And if, you know the rule, I mean, I think it's cute and safe to say what that guy did is appropriate. And, you know, it's also based on whether this girl is interested. And most likely they have a lot of friends, mutual friends in common. And she can, she'll probably check that out and go and ask around her friends, get his story before she probably responds. And that's the thing is it's going to be based on those mutual friends and what they have to say about him.

[Host/Interviewer]

Well, what she did do is she immediately defriended him, which we found amazing.

[Jen or Wendy (Co-host or Guest)]

She blocked him.

[Host/Interviewer]

Blocked him, right?

[Jen or Wendy (Co-host or Guest)]

Yeah.

[Host/Interviewer]

And so he couldn't contact her anymore, which led us to believe that she was a psycho. And he.

[Deborah]

My rule with guys that I don't know, strangers sending me a private message saying that they think I'm cute and would I want to go out sometime, I ignore all of them, every single one of them. If you give me a generic Facebook private message the same way you would give me a generic text message, I just, I don't think you're putting in effort. I think it could be a mass message that you copy and paste to a bunch of girls.

[Jen or Wendy (Co-host or Guest)]

Right.

[Deborah]

If you want to make yourself stand out, then you need to. I don't, you know, what you said, what this guy did, where he, he mentioned a party that he knew she was going to, which could be a little bit crazy on his end. But if he, if he had said something, you know, that they had in common and I know your friend, this person and that sort of stuff, if you make it personal that, you know, a girl knows you didn't just copy and paste it, I think that that's better for you. I mean, it gives you a better step ahead in the right direction.

[Host/Interviewer]

What about the issue of infidelity online? Like once you're exclusive with someone, are you allowed to comment on members of the opposite sexes pictures?

[Deborah]

Yeah, if you do it very lightly. I mean, if you don't say anything inappropriate. Absolutely. Because you know that, you know it says it on your page that you just talked about somebody else's photo. So your significant other is going to check that out if she's able to. And also there's a level of trust that you have to have. You know, with social media.

[Olivia]

I actually though, I mean, a little story like we have, there's someone I know that is in a relationship with someone else living with them and on Facebook and it does so on their status. However, they continue to. Guy continues to hit on other girls and it's like you have to be, I mean, none of these girls, I mean, he's a really good looking guy. He's got a lot going for Him. But, like, are you serious? Like, there's pictures posted of you and your girlfriend everywhere. It says in a relationship with blank. I mean, I don't know what people are thinking that that's okay to do a huge weird thing to me.

[Jen or Wendy (Co-host or Guest)]

Let me ask you guys about chivalry, because a lot of people would argue that chivalry is dead and that technology makes it EAS even more easy for chivalry to be dead. How does a single girl navigate, you know, being in the world of texting and social networking while dating? Because it's just a part of it now. You know, there's no avoiding. That's just. That's just the way it goes now. But still being able to expect to date a gentleman or expect some chivalry at some stage of the game.

[Deborah]

I think it's about mixing it up. I mean, it's about knowing that a guy that really likes you will call you at some point and hopefully early on to make a date. But we'll use texting to flirt with you. We'll send a funny post on your Facebook page when he's thinking of you and he's going to mix it all up.

[Olivia]

Mm, no, it's true. I mean, I think, you know, the most important thing is I think if you have to wait for that phone call, I mean, I think that is kind of all these social media, everything that's going on, whether he Facebook see you and get your phone number that way, like, it's got to come down to the phone call. Right?

[Jen or Wendy (Co-host or Guest)]

Okay.

[Host/Interviewer]

So it's like phone call, like in person, like talking.

[Olivia]

Yes.

[Jen or Wendy (Co-host or Guest)]

I'm striking.

[Deborah]

Do you remember that?

[Jen or Wendy (Co-host or Guest)]

Hearing their voice? Yeah.

[Host/Interviewer]

I don't understand.

[Deborah]

Yeah, you can still place calls on your phone.

[Jen or Wendy (Co-host or Guest)]

I know you can express so much more with your voice than your thumbs. Jeff.

[Host/Interviewer]

Hey, Deborah and Olivia, thank you so much for joining us today.

[Olivia]

Sure.

[Jen or Wendy (Co-host or Guest)]

Thanks you guys.

[Host/Interviewer]

I appreciate it. And the name of the book is called FlirTexting.

[Deborah]

FlirTexting. Yeah.

[Jen or Wendy (Co-host or Guest)]

It's really good and it's awesome book. It's such a great book. I have used it more than one time as, like, a guide for how to do it.

[Deborah]

And do we have to have to tell you one more super big tip about Facebook?

[Host/Interviewer]

Yeah, go ahead.

[Deborah]

Olivia and I were doing sort of a Facebook makeover bootcamp with some of our guy friends, and we noticed that a lot of our guy friends have absolutely ridiculous photos. And when a girl gets a guy's number, the first thing she's going to do, whether she's friends with you or not is check out your Facebook profile. So you have to make sure that that picture is very, very wonderful and you're not doing anything in it that she could disagree with. So if you go to flirtexting.com on our blog today we've listed the 25 worst things you could possibly be doing in your Facebook profile picture.

[Host/Interviewer]

We'll link that up to our website.

[Deborah]

Great.

[Host/Interviewer]

That's very cool. Thank you guys.

[Deborah]

Thank you guys.

[Host/Interviewer]

Have a great day. Have a great week.

[Olivia]

Thank you too. Bye.

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