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Game Time: Red Flags and Green Lights: Navigating Midlife Dating Like a Pro
Bonus Episode23rd October 2025 • The Iconic Midlife with Roxy Manning • Roxy Manning
00:00:00 00:12:31

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We dive headfirst into the whimsical world of midlife dating, where the stakes are high and the rules seem to change with every date. The main highlight? We play a cheeky game called "Red Flag, Green Light," dissecting various dating scenarios and determining whether they signal a potential winner or a hard pass. Think of it as a guide through the murky waters of romance, where we tackle everything from a guy who’s never been married to one who asks for your Venmo on the first date. Along the way, we sprinkle in some wisdom about the nuances of relationships, reminding ourselves that every situation is as unique as a fingerprint. So, grab your headphones and get ready for a blend of fun and insightful banter that might just help you navigate your own midlife dating escapades!

Takeaways:

  • This episode dives deep into the complexities of midlife dating, addressing the nuances of relationships and the various red flags to watch out for.
  • We explore the idea that individuals often have different communication styles that can lead to misunderstandings in romantic relationships.
  • Playing games like 'Red Flag, Green Light' provides a fun framework to discuss serious dating concerns while keeping the conversation light-hearted and engaging.
  • The hosts emphasize the importance of assessing character over superficial traits when evaluating potential partners in midlife dating scenarios.
  • Listeners are encouraged to be open-minded and understanding about the quirks and habits of their partners, recognizing that not all behaviors indicate red flags.
  • The discussion reinforces the notion that not all relationships will fit perfectly, and that's okay; it's all about finding the right match for oneself.

Transcripts

Renee Rouleau:

Foreign.

Roxy:

You know, it would not be the iconic midlife if we did not play a game.

Renee Rouleau:

Exactly. We love games.

Roxy:

Are you ready for another game?

Renee Rouleau:

Yes.

Roxy:

I've got a fun one, lady.

Renee Rouleau:

This one.

Roxy:

This one is called Red Flag, Green light.

Renee Rouleau:

So. Okay, we love that. Yes.

Roxy:

We're gonna. We're gonna. I'm gonna describe a man, like, some tendencies or something he does, and you say if it's a.

Or a green light for potential midlife dating situations.

Renee Rouleau:

Okay.

Roxy:

Okay. He's never been married.

Renee Rouleau:

Green. Green light. Okay.

Roxy:

So, like, if he's, let's say 50, 55 and never been married, that's okay, right?

Renee Rouleau:

Let's. Let's not. Let's not make assumptions here.

Roxy:

Okay.

Renee Rouleau:

Okay.

Roxy:

Good call.

Renee Rouleau:

Some people are late bloomers.

Roxy:

That's true. That's true.

Renee Rouleau:

And that's okay. And that's okay.

Roxy:

That's okay. That's absolutely okay. Okay. He's in his 50s and he lives with his mom.

Renee Rouleau:

That would be a red flag. Yeah. Yeah.

Roxy:

You're like. And in the basement, too. Like.

Renee Rouleau:

I know, right? But. But I mean. I mean, except, I mean, is she elderly? He's a caretaker for her. You know, depends on the situation.

But in general, I think most women would like an independent. A man that lives independently.

Roxy:

Yes.

Renee Rouleau:

You know, or not with his mom.

Roxy:

Exactly. He asks you for your Venmo in the first week.

Renee Rouleau:

I think that's a green light. Is he sending me, like, is he reimbursing me for half the meal I paid or.

Roxy:

Could be.

Renee Rouleau:

I don't know. Yeah, I don't. I don't. I don't know. I haven't had many Venmo experiences, so I don't know. What's there an ulterior motive there? That's. No.

That's a good question. Yeah, I mean, I mean, maybe. Maybe a true gentleman would all of a sudden Venmo me because he's like, hey, let me take care of that Uber that you.

That you took. I'd like to cover that cost. Or. I don't know.

Roxy:

As long as he's sending payment and not payment requests.

Renee Rouleau:

Oh, okay. Oh, so sending a Venmo means he's asking for money?

Roxy:

Yeah.

Renee Rouleau:

Oh, okay. Sorry. I thought it just meant, like, share your Venmo. I don't know. Okay, so yeah. Yes, that would be a red flag. Yes.

Roxy:

His ex, who's a girl, is still his best friend.

Renee Rouleau:

His ex, who is a girl, is still his best friend. Green light. I have no issues with that.

Roxy:

Okay, so there's no jealousy?

Renee Rouleau:

No. I mean, I'M I think it's, you know, it's important to understand the state of the relationship and what it is.

But I think, you know, in this life, you know, there's very few people that we have true, close connections with, and if. If they're great friends and. And it has. It's clear that there's not something to it. I'm going to give the benefit of the doubt.

Roxy:

Okay. He has no social media footprint or presence at all.

Renee Rouleau:

Green light.

Roxy:

Oh, okay, so that would not scare you off?

Renee Rouleau:

No, I mean, I think. I mean, some people are private people.

You know, my late husband, he had a little social media presence, but my husband didn't trust anybody and he didn't like himself out there, and he just liked privacy. And the reality is I, you know, I kind of can't be that private because, you know, my name is my brand and, you know, I have to have a presence.

But I am far more private now than I ever have been because. And, like, I don't post my love life. I haven't posted any pictures of my relationship with my boyfriend at all because there's power and privacy.

So I think that we've all gotten kind of used to that. You have to, you know, have a presence online. But now, I mean, are they on LinkedIn? Are they somewhere? I don't know. It just.

It depends on what they do for the living. A living as well.

Roxy:

That brings me to my next one. He's charming, but vague about his job.

Renee Rouleau:

I would say that is a red flag.

Roxy:

Okay, so you'd say hold off on that one maybe.

Renee Rouleau:

And when in doubt, hire a private investigator. I mean, this is the thing, too. Like, I don't, you know, I mean, just.

Ladies, you have that in your back pocket, you know, like, especially if you've been dating someone for a while or something. Like, I mean, you hate to do that, but, I mean, if you really want to know and you don't have time to waste, hire a PI if you really want to.

Roxy:

Yeah, good point, Good point.

Renee Rouleau:

I mean, they'll find everything on someone. Trust me, they're good at their job.

Roxy:

Real quick. Okay, he is 15 years younger than you.

Renee Rouleau:

Green light. Green light. Whatever works. Whatever works. Okay.

Roxy:

He refuses to take selfies with you. He refuses or, like, be in pictures with you?

Renee Rouleau:

Well, I mean, I don't post pictures of me and my boyfriend, but we take selfies. Do you mean taking selfies and posting it and sharing it?

Well, then it's a green light because some people are private, you know, I mean, I And I just, I think that again, there's power and privacy. So I don't, I mean, I have to understand the context of it.

But also some people, which I love, like, some people are very conscious of when they're out with people to not be on their phones. Right. And like, why do we need to have a picture of every occasion? Like, we don't. Like, how about we just put our phones away and we'd be present?

So I think it just depends on the context of what that is. Yeah, so it's kind of depends. But I think, but I think, I think we need to be taking less selfies, basically what it is, Right.

We don't need to take selfies and have to document every moment. I think sometimes just being present and not having our cameras and phones out is nice too. Yeah.

Roxy:

He only text, never calls.

Renee Rouleau:

Well, I think, I think it just, I mean, I'll say a green light only because we can't always assume that people are doing something nefarious. Right. So we, it's like listen to what they're saying, I guess. I mean, some people. Now I'm in a long distance relationship.

He happens to like, you know, he enjoys talking on the phone. My husband hated talking on the phone. Now we live together, so that's a different story.

But I could never be in a long distance relationship with my late husband because it never would have worked because he didn't like to talk on the phone. And that's okay. He didn't like to talk on the phone. That just wasn't right for me. And especially doing long distance, right?

So I just think, I think especially, you know, as I said, we need to understand what men, what men's needs are. Women, we love to talk. Men don't, they don't like to talk on the phone. They're not talkers. They're just not.

And so again, you have to decide, like, am I okay with somebody who's not a big talker? If that's not right for you, then go find somebody else who does like to talk on the phone.

But again, we have to understand that men are from Mars, women are from Venus. We're wired differently. And that's okay. It doesn't make someone bad. It's just you have to decide. Does that work for you?

Roxy:

Yeah, absolutely. He wants to split the dinner bill. Exactly. Like to the penny.

Renee Rouleau:

To the penny?

Roxy:

Yeah, like, you know, 52.36 or something. Like to the penny.

Renee Rouleau:

Okay, so I will, for me, I don't like anyone who's anal and that sounds like it's anal. So. But guess what? Some. Some women are anal. Some men are, you know, anal. So if they're.

If that's their little thing that's important to them, then great, if that works for you. But you know that. That wouldn't be for me. But that doesn't mean it's wrong.

Roxy:

What about if he wants to split the bill on the first date? Like dinner bill?

Renee Rouleau:

I think that's fair. I think that's fair. I mean. I mean, also, I'm an independent woman, so I'm kind of okay like that. But, I mean, it depends on the context, right?

If a guy pursued you and he's taking you out, then of course he should pay. But if. If somebody's like, I don't know, if a friend's just kind of setting. Setting you guys up, it's like, hey, I think you guys should date.

But, like, neither one really pursued the other one, and you kind of. Someone set you up. Then it's like, you know, we don't know if this is going to be a love connection.

I'm just trusting this friend that put me on this blind date. So in that case, it's like, yeah, we may be.

We're just kind of getting together because we're doing it as a favor for our friend because they think we should meet, but it doesn't mean that it's going to be a romantic, you know, connection. So I think if that. In that scenario, then it's like, no, we. We split it.

Roxy:

Okay, that's a good point.

Renee Rouleau:

Yeah.

Roxy:

If you're not being. If one isn't chasing the other sort of a thing.

Renee Rouleau:

Exactly.

Roxy:

Yeah. Yeah, that's fair. He tells you he loves you on week two.

Renee Rouleau:

Well, yeah, I would say that's a red flag. That's. That's a little much. Especially because men, notoriously, they don't hand that out. They don't hand I love you out like trick or treat candy.

Right. So they hand it out when it's really meaningful. So if he's saying that too quickly, that. That. That wouldn't be right for me.

Roxy:

Yeah, that would feel a little weird. A little off.

Renee Rouleau:

Yes.

Roxy:

Well, Renee, you have passed the test with flying colors.

Renee Rouleau:

I know. I wish everything was so black and white, but in humans, everything is just not so black and white.

And as you can probably tell, I give people the benefit of the doubt, because inherently, humans are good people. You know, there's always going to be a small percentage that are not. But by and large, I think we all.

I Know, we all want the same things in this life. We want to be happy. We want to be loved. We want to, you know, we want to love and be loved. We want to be accepted for who we are.

Um, you know, we want to be able to put a roof over our head. We all have the same fundamental needs, both men and women. You know, there's no. There's no bad guy. You know, there's. You know, there's good guys.

There's plenty of them. And my wish is that women just give men a little more grace and just accept that they're not like us. They're not like us. They never will be like us.

And, you know, and we need to.

Roxy:

Accept that they have their own factory settings. I mean, totally different.

Renee Rouleau:

Yeah, Right.

Roxy:

And not to say we can't change those. I mean, not change them, but, you know, you can kind of like.

Like you were saying earlier, tell them what you love and what you like and, you know, the things that you want, because they're also not mind readers, you know, so you kind of.

Renee Rouleau:

Exactly.

Roxy:

Right.

Renee Rouleau:

And at a certain point, if you're sharing what you need and they're not able to meet that, then he's not the right one for you. So you can't get mad at him because, oh, he needed to be this, that, and the other thing. Some people aren't able to do that for you. Right.

And that's okay. And that's up to you. Just at some point, say, this is no longer right for me. I've expressed my needs.

I've said what's important, and he's not able to do that for me. But there'll be someone out there that would be open to that.

And so it's not, you know, yelling at each other and thinking that, you know, people are awful. It's just like, this wasn't a fit.

Roxy:

It wasn't a fit.

Renee Rouleau:

It wasn't a fit.

Roxy:

And no hard feelings, like, just move on and go on with your life. Right, Right.

Renee Rouleau:

Yeah. Because trust me, we're not the fit for everyone either.

You know, I mean, I know we act like we're all high and mighty, but we're not the fit for everyone either, too.

Roxy:

It's true. It's true. It's.

Renee Rouleau:

It's.

Roxy:

You know, it goes both ways, right?

Renee Rouleau:

It goes both ways. Absolutely.

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