Dating Intelligently 6: Dating Red Flags & Boundaries

Author(s): Scott Douglas Jacobsen

Publication (Outlet/Website): The Good Men Project

Publication Date (yyyy/mm/dd): 2025/11/01

Christopher Louis is a Los Angeles–based international dating and relationship coach and the founder of Dating Intelligence. As host of the Dating Intelligence Podcast, Louis draws on intuition and lived experience to guide clients toward authentic selves and meaningful romantic connections.

In this exchange with Scott Douglas Jacobsen, Louis surveys enduring red flags—self-absorption, ex talk, and rude manners—and newer ones: chronic phone use and love-bombing. He links patterns to anxious and fearful attachment styles. Among professional “alpha” clients, over-filtering and impatience can eclipse good matches; less secure daters “audition” rather than observe—social media fuels labels, subtweeting, and vaguebooking, eroding privacy-as-dignity. Post-MeToo, respecting boundaries has evolved from chivalry to consent. Louis’s season premiere with Brande Roderick explores LAT as a workable model. His remedy: presence, empathy, and perspective.

Scott Douglas Jacobsen: All right. Once again, we’re here with the charismatic Christopher Louis. We’re going to be talking about red flags. This is a big topic, but it’s always good as a refresher course because we all forget what red flags, green flags, yellow flags, and so on are. You work with active clientele, and people pay you for your advice and feedback.

Louis: That is correct.

Jacobsen: What comes up for you? And your first episode is out now, right?

Louis: That’s correct. Thank you. My first episode of Dating Intelligence for the new season premiered last Tuesday. It features Playboy Playmate and Baywatch star Brande Roderick. She is the premier guest co-host for this new season of Dating Intelligence. It went really well, and we discussed LAT (Living Apart Together). She and her partner actually live apart together—he lives right behind her. They live in separate houses, backyard to backyard.

Jacobsen: That could work.

Louis: It does for them. They’ve been together for years, and it works quite well.

Jacobsen: When you see red flags in your business and when people come to you, how do you identify one? How do people present red flags to you, and how do you identify red flags about them or about the people they’re discussing—things they may not be acknowledging when they describe their situation to you?

Louis: Hi, Scott, thanks for having me. With the people I coach, most of my clients who have red flags tend to fall into either the anxious attachment style or the fearful attachment style. What happens with that—starting with women first, and then I’ll talk about men—is that women often tend to be quick to talk about marriage and children. They’re usually in a hurry. Many feel like there isn’t enough time, especially women in their mid to late thirties, whose biological clocks are ticking. They want to push the issue of marriage and children a bit faster. That can be a red flag for men, rather than just letting things go where they naturally go. Even though you can bring that up on the second or third date, I always tell people that on the first date, you want to get to know the person. Have fun, see if there’s a connection, and then you can ask, “What are your views on marriage? What are your views on children?” When it’s pushed too quickly, it’s a red flag for most men because they’re either caught off guard by the question or unsure whether you’re the right person even to be thinking that way.

Now, on the flip side, for men, their red flags often come from talking too much about themselves and focusing on their possessions. There’s nothing worse than a man on a date talking endlessly about himself—what he owns, how much money he has, how much he paid for something, or showing off what he can afford. That’s a major turnoff for many women because it comes across as egotistical.

As for other red flags on first dates, what I tell my clients to look for are straightforward things. I always ask, “What are your three red flags?” They’ll usually come up with examples such as someone who talks too much about themselves, is rude to others, or constantly talks about their ex. That last one is big—talking about your ex on a first date, especially in a negative way. It shows a lack of empathy in the moment. No matter what your ex did, they shouldn’t be put on blast to someone you’re just starting to date. And if you talk about your ex in a way that shows you might still be in love with them, still have feelings, or wish you’d never broken up, that’s another huge red flag for the other person.

Jacobsen: How does this work for gay and lesbian matchmaking? Are the same principles involved?

Louis: It’s very similar in the LGBTQ community as well. There will always be an alpha and a beta in these situations. Everyone has tendencies—whether they’re rooted in insecurity, jealousy, rudeness, or controlling behaviour. These traits can appear in anyone. This crosses all boundaries: ethnicity, nationality, gender, or orientation. Whether it’s a woman dating a woman, a man dating a man, gay or lesbian relationships, red flags tend to be universal.

Jacobsen: Are there unique American qualities that are seen as red flags?

Louis: That’s an excellent question. I’ll say no to that, because people are people. If we talk about etiquette and manners, that applies everywhere. If you don’t have manners, that’s an issue no matter where you’re from. If you’re rude to servers, the valet, or anyone around you on a date, that’s a universal red flag. Insecurities and controlling behaviours are the same across the board. There isn’t a specific American or Canadian difference. What might differ is how forgiving or polite people are, depending on their culture. Some may avoid speaking up immediately because they think it’s inappropriate, a view that may also be influenced by religion. Certain religious or cultural norms can shape what’s considered acceptable behaviour in relationships.

Jacobsen: Most of your clientele are professional-level women, correct?

Louis: Yes.

Jacobsen: What trends do you notice among them—what they identify as red flags? How does that change across this arc? Because you mentioned mid- to late-thirties women who want children often feel a greater sense of urgency. But what about more broadly?

Louis: Let me start with the first part and break this down. Women in business—my high-level clientele—are usually more established. They can afford their own lifestyle and are very clear about what they want from dating. This can make things difficult because these women, whom I call “boss” or “alpha” women, tend to be less tolerant. They already have their three non-negotiables set and know exactly what they want. The man sitting across from them might be a great person, but because they’re dominant in their professional space, that control sometimes carries over into their dating life. The balance can get skewed. They’re often more impatient and think they know exactly what they want, dismissing potential matches too quickly. As a result, they sometimes overlook genuinely good partners because they come in with an agenda—expecting a certain calibre or lifestyle.

You see this in matchmaking, too. Many matchmakers say they’ve had clients reject five or more dates in a row simply by reading profiles and deciding, “This person isn’t for me,” even when the profile actually fits what they claim to want. The same thing happens with men—it goes both ways.

Now, on the other side, I also work with women who aren’t as financially successful but are more insecure. They tend to “go with the flow.” They want a guy to like them. They’re looking for someone who shows genuine interest in them.

They’re less likely to pick up on red flags as quickly as others because, as I tell them, they’re auditioning for the guy instead of the guy auditioning for them. I always say, “Why are you auditioning for him? The guy should be auditioning for you.” You should sit back, observe, and see if he’s listening, communicating well, and showing emotional intelligence—rather than putting on a show to impress him. Then you realize you thought the date went well, but he doesn’t call back for a second one. That’s a problem because they’re not recognizing their own red flags or the ones the man is showing. They’re more tolerant than others.

Jacobsen: How many of the clients who come to you in their thirties arrive with negative attitudes about dating in general—either from bad experiences or frustration?

Louis: It’s about half and half. Half feel like there’s just no one out there for them because they can’t find a profile that matches what they want. The other half are genuinely discouraged, saying things like, “I’ve been on all the dating apps. I have dating fatigue. I can’t find the right guy. Is there even one person out there for me?” With those clients, I have to focus on rebuilding their self-image and self-worth. With the more established women, I have to help them tone things down and step out of their alpha mode—to reconnect with their feminine energy and openness.

Jacobsen: What about online content that isn’t from real experts? Do you have clients who absorb that material and then come to you needing to unlearn it—so you can bring them back to a healthier balance?

Louis: Yes, absolutely. I have one client who actually goes to his “best friend,” ChatGPT, and uses it as a secondary dating coach. He’ll ask, “What do you think about this?” or “I went on a date—here’s my summary—can you break it down for me?” He’ll then come back to me with all this data and say, “Here’s what ChatGPT told me.” I tell him, “Okay, I see this, but you’re missing key details. How did the date actually go? How did you feel?” ChatGPT can only give him the general averages of what usually happens, but it can’t reflect who he is or how he showed up. He’s feeding the AI what he thinks happened, not what really did. So I have to walk him through that and get him back to real, human insight.

Jacobsen: What about contemporary factors—things like social media, which didn’t exist in earlier dating eras? How does it play into red flags today?

Louis: Social media plays a huge role now, in several ways. It’s introduced new terminology—gaslighting, breadcrumbing, benching, ghosting—all of which shape how people interpret dating behaviour. People see a post or a TikTok explaining these terms and immediately apply them to their own experiences. They also hear others’ stories about bad dates or relationships online, and that colours how they view their own. Dating apps themselves function as a form of social media, with people sharing experiences and asking for feedback. Sometimes they get good advice, but often it turns negative, becoming a kind of mob mentality where everyone piles on instead of helping someone reflect honestly. It amplifies anxiety and judgment instead of empathy and understanding.

Jacobsen: There were two more sophisticated ones—let’s run through one or two. In one instance, a solution is to disassociate—not disrespectfully—but to say, “Thank you very much, take care,” and ensure communication is clear. One is subtweeting. Another is vaguebooking. So, to define them: vaguebooking comes from Facebook—it’s cryptic, emotional, and dramatic without naming names. 

Subtweeting comes from “sub,” as in subtext, and “tweet,” as in Twitter—or X now. It’s when someone talks about another person without tagging them, so everyone knows who they mean, but technically, they didn’t say it. That’s where the passive and relational aggression comes in. It’s important to acknowledge it calmly when it happens, communicate explicitly but not excessively, and then disengage if needed. That approach came up in another interview with a family and relationship therapist who focused on trauma.

Louis: Right, and my feelings on both of those are that when people go online to subtweet or vaguebook, they’re really looking for validation. If you’re airing your dirty laundry online, unless someone has done something truly awful to you, it’s unnecessary. For example, about a year and a half ago, there was that viral story in New York about a man who dated hundreds of women. 

These women eventually found each other and created a Facebook group dedicated to him, realizing they’d all dated the same guy. Good for him for his popularity, but the point is that they publicly exposed him because he’d misbehaved. In a case like that, fine—there’s a justification. But if you’re too uncomfortable to break up or have an honest conversation—just saying, “It was nice seeing you, but this isn’t working out”—then posting about it for validation is the wrong approach.

That’s what social media has become, however. Everyone puts their lives out there—TikToks, dances, comedy clips, bloopers, people falling or embarrassing themselves—it’s all public. No one keeps things private anymore. People rarely process experiences privately; instead, they post and let strangers judge.

Jacobsen: When it comes to that kind of behaviour, you have to make an individual judgment about what you’ll tolerate, and once you decide, you have to own it. Whether you allow it to continue or respond in a calm, dignified way—that’s a matter of personal integrity. What this brings to mind for me is the idea that privacy is dignity. We still have some of it left, though we’ve lost a lot in the internet era. When you’re working with professional clients, do you incorporate that idea—privacy as a form of dignity—into your advice?

Louis: Yes, I do. I always consider everything, but I also have to be mindful of how people are feeling. Sometimes clients share things that, in my head, seem trivial or avoidable—I might think, “Really? You couldn’t see that?” But those are their genuine feelings and experiences. I have to take it seriously and be fully present for them, no matter how small it seems to me. It’s similar to journalism—you might write something from your perspective, but someone else with all the facts might correct you. That’s what I do with my clients. I guide them toward perspective.

Sometimes, I have to mute my phone, shake my head, or chuckle because what I’m hearing is so unexpected. But these are real issues in their lives, and my job is to meet them where they are. Whether it’s a client who uses ChatGPT as his “best friend” for dating advice or someone asking about something they saw online, I have to listen and make a thoughtful, professional judgment.

Unless it’s a friend —Scott — or a close friend, then I’ll say, “What are you doing?”

Jacobsen: Sure. Then you’re allowed. Friends are the ones who’ll talk trash to your face but speak well of you in public.

Louis: Friends are off limits. I’ll tell them, “You’re being dumb.”

Jacobsen: Three questions. What are the old red flags that are still around? What old ones have evolved? And what are the brand-new ones?

Louis: Let’s start with the old ones—the tried and true. The first three would be talking about yourself too much, talking about an ex, and poor manners or etiquette, which includes being rude. Those have never gone away.

As for newer red flags, one of the biggest is constant phone use. People bring their phones to dates, keep checking them, scrolling, texting—it’s a major red flag and just plain rude. Another one is love-bombing. It’s been around forever, but the term itself is more widely recognized now. It’s when someone showers another person with excessive affection early on, often coming from insecurity.

And an older one that’s evolved is respecting boundaries. Decades ago, men often took the lead—they’d order for women or make decisions for them. That behaviour doesn’t align with today’s norms, especially in light of the MeToo movement. You have to be conscious about respecting autonomy and comfort levels.

Talking about your ex used to be more common. Dating was more conservative—you’d pick someone up, meet their parents, maybe bring flowers. Back then, people would often compare their date to their ex, saying things like, “My last partner never did that,” or, “You do this so much better.” Whether positive or negative, those comparisons were a way to process and move forward. It was a bit more accepted then than it is now.

Jacobsen: What about overthinking? People not doing the obvious thing—just putting themselves out there?

Louis: Yeah? What do you mean exactly? Give me an example so I’m on the same track as you.

Jacobsen: They keep coming to you for advice, taking notes on their phone or even in a notebook. They thank you, they go on a few dates, maybe cancel at the last minute—but they’re not actually being proactive about dating.

Louis: That makes sense. That’s rooted in insecurity, maybe introversion. If you’re unsure of who you are when dating—and you should always just be yourself—that uncertainty can turn into imposter syndrome. I had a client once who told me he just wanted a woman to like him for who he really was. He admitted that on previous dates, he’d pretended to have more money than he actually did. He’d built up this façade, but by the third date, he couldn’t sustain it. He was insecure about his true self, convinced that women wouldn’t like the genuine him. But he was still going on dates, so clearly, he had something going for him.

Jacobsen: Thank you for the opportunity and your time, Chris.

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