As a man who’s dated a significant number of women in my lifetime, I’ve (unfortunately) had my share of situations where I’ve dated red-flag women.
Sometimes these were short overnight hookups, but some of them even stretched into longer-term flings or even full-blown relationships.
At times, my inexperience kept me ‘blissfully ignorant’ of the red flags until it was too late to avoid disaster. And sometimes, I would willingly go ahead and date the woman in question anyway, for one of any number of complicated reasons:
- She was hot, so I willingly took the risk
- I got super emotionally attached, so the red flags became ‘less noticeable’ to me
- Our sex was so good that I decided a ‘calculated risk’ was worth it
- At the time, I felt like I wouldn’t be able to meet or date anyone healthier and better-suited to me due to not believing I was attractive or desirable enough to do so
But by far the most dangerous situation that a man can find himself in when it comes to red flags is this:
He starts dating a woman who exhibits one or more red flag behaviors, but either by inexperience or due to emotional blinders, he fails to recognize the danger and attaches himself to her anyway.
This kind of ‘blind slaughterhouse’ scenario is exactly what you want to avoid as a man.
Don’t get me wrong. Sometimes, as men, we choose to take ‘calculated risks’ with women on a short-term basis because the sex, the excitement, and the thrills are just too damn good.
But at least when you knowingly engage in such affairs, you’re walking in with your head on your shoulders—and you can keep your eyes peeled for danger.
The unknown dangers, by contrast, are those that pose the greatest risk.
So in this guide, you’re going to learn exactly how to identify the most crucial red flags to look for in your dating partners—to help protect yourself from harm while also cultivating a masculine dating life that you can actually enjoy.
What Is the Meaning of a ‘Red Flag’ When it Comes to Dating?
I define red flags as behavioral or lifestyle symptoms of deep-set destructive, chaotic, or dangerous belief systems or thought processes.
So, for example, I call ‘entitled behavior’ a red flag because it’s a direct symptom of something deeper and much more destructive than just the behaviors that an entitled person might exhibit on a day-to-day basis.
Entitled behavior is actually an indication of a deeper mindset issue. A woman who’s truly ‘entitled’ believes that everyone else in the world owes her a certain standard of treatment, regardless of whether or not she’s actually done the work to earn that treatment.
This is obviously problematic—and thus, why every red flag I’ve listed in this guide is actually a behavioral symptom of a much deeper and more sinister inner belief system that, quite honestly, as a man, you shouldn’t want to tie yourself to in a long-term life partner.
So date and mate carefully, gentlemen. Here are the signs to watch for.
12 Biggest Red Flags for a Girl: Look Out for These At Any Time
Entitlement is basically an inner-held perception where a person believes that they deserve special treatment or privileges just because of who they are or what they have.
It can manifest itself in a number of ways. Entitled people may:
- Expect people to always be available
- Feel like they are owed certain things (money, priority, special treatment, etc.)
- Be unwilling to make compromises or change problematic behaviors
- Make unreasonable demands that don’t take your feelings (or even rationality) into account
In my opinion, an entitled mindset is one of the biggest red flags to look for in a dating partner.
These women can be very charming and attractive at first glance, and this mindset can even come off as ‘cute’ in the short term. But in a long-term relationship, it’s incredibly destructive.
We all tend to deal with at least a small level of indecisiveness in our own lives. But at major levels, where people actually get crippled by their inability to make decisions and move forward in life, this can be very destructive.
Here are the major aspects of this red flag to watch out for:
- She doesn’t know what she wants in life
- She can’t make decisions about her life trajectory, which leads to analysis paralysis and doing nothing at all
- She can’t decide which dating partners she likes, so she never commits to one and/or keeps men from her past around
- She’s too afraid of walking away from things to choose to commit to important new things, which leaves her stuck in her current life state
On a minor level, indecisiveness is a pretty normal human issue. But at debilitating levels, this behavior can be problematic and difficult to unravel—and it’s better not to get too involved with people who get paralyzed by it.
3. Emotional Unhealthiness
There are a number of unhealthy emotional states to watch out for in your dating partners.
Some of these include:
- Excessive and/or consistent negative thinking patterns
- Suppressing emotions
- Addictive behaviors (including social media addiction)
- Extreme jealousy
- Overly competitive
- Unresolved trauma
We all deal with some levels of these things in life. But you also want to make sure that the people you’re dating aren’t exhibiting debilitating or uncontrollable levels of emotional unhealthiness.
4. A Lack of Intentionality
Intentional living is crucial not just for every individual, but also for partners who want to move forward in life together as a family unit.
And dating someone who displays a lack of intentionality in life is going to be problematic for this process.
Be on the lookout for the indicators of this red flag behavior. Women who lack intentionality will:
- Neglect general life goal-setting
- Fail to make detailed plans
- Not have a set, specific purpose in their life
- Not be able to articulate exactly what they want to do, be, have, or accomplish
- Be more likely to drift chaotically through life than to make structured plans and execute them
It’s always best for men not to get too involved with these types of women.
5. A Victim Mentality
A victim mentality is a way of thinking and seeing the world where the person sees their life as a place where they’re powerless to change their circumstances, where everyone is ‘out to get them,’ where their life is uncharacteristically unfair, and/or where they basically can’t or don’t expect for their actions to be able to positively impact their future outcomes.
People with a victim mentality will:
- Complain a lot
- Cry about how life is unfair
- Maintain a pessimistic, cynical, and/or negative perspective of life and the world
- See themselves as powerless to fix their problems
- Blame their problems, challenges, and suffering on anyone other than themselves (other people, their boss, the government, their past, their parents, society as a whole, etc.)
- Be less motivated to take action or stick with plans because they’re less likely to believe that their actions can fix anything
This kind of person is also highly likely to only say negative things about all of their exes instead of taking responsibility for their part in their own failed relationships.
The victim mindset is literally a poisonous mindset for people who want to better themselves and succeed under their own power. Thus, it’s never in your best interest to date someone who’s trapped in a perpetual victim mentality in life.
Lazy people are going to be much less likely to want to work together with you to move toward a state of greater success in the future—and this is obviously problematic.
Here are some signs that may point toward the fact that the woman you’re dating is actually lazy:
- She does a lot of procrastinating
- She’s disorganized
- She’s unmotivated to take action or accomplish things
- She’s unreliable and seems scattered
- She doesn’t seem interested at all in taking action for personal growth
- She’s all too willing to let someone else do the hard work so that she can relax
These types of women are sometimes fun to date in the short term, because they’ll be more likely to want to put their work, chores, and responsibilities aside to go on adventures with you.
But in a long-term partner, laziness will spell disaster for your future life and relationship together.
7. Chaos and Drama
Chaos and drama slow down progress, cause needless problems, hinder plans and goals, and get in the way of success.
They can also be costly to your life in a myriad of other ways. Thus, it’s going to be crucial that you stay away from dating partners who are constantly embroiled in chaos and drama in their own lives.
So avoid becoming entangled with dating partners who:
- Entertain negative friends
- Always seem to be in the middle of drama and fights
- Are always talking about their problems instead of actively finding solutions
- Often show up late or cancel plans due to some kind of drama
- Try to control people or circumstances around them via dramatic manipulation or other unhealthy social impulses
By contrast, dating a woman who has a drama-free life, who helps to create order around her, is like a breath of fresh air and will help you as a man to make your life even more structured, orderly, and successful.
Dishonesty is a destructive behavioral trait that erodes trust, creates misunderstandings, and ultimately undermines the foundation of a healthy relationship.
When considering a potential dating partner, avoid women who:
- Habitually lie or deceive others, even in seemingly insignificant ways (it’s the behavior that counts, not necessarily the scope of the deceit)
- Display a lack of transparency or refuse to communicate openly about their thoughts, feelings, or past experiences
- Engage in secretive behaviors, such as hiding their phone, evading questions, or acting suspiciously
- Manipulate the truth to serve their own interests, disregarding the impact it may have on other people (especially in their intimate relationship)
- Break promises or consistently fail to follow through on commitments
The truth is that trust is an essential building block for long-term relational success.
Choosing a partner who values honesty will empower the two of you to foster an environment of trust, openness, and authenticity together.
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The problem with irresponsible people is that they can’t be trusted with the important stuff that needs to be taken seriously in order for life to move forward (and for the relationship to succeed).
Here are some signs to look for that may indicate that the woman you’re dating is an irresponsible person:
- Often late or canceling plans
- Always making excuses for why important things don’t get done
- Not good at follow-through
- Not good at self-care or caring for her house, pets, kids, etc.
- Bad time management
- Poor with money
- A history of bad decisions that could have been avoided by critical thought and responsible action
It’s always better to avoid dating irresponsible people—because in time, their irresponsible behavior will spill over into your life and affect you as well.
Cheating should be considered an absolute deal-breaker in any relationship. And as a man, you should have a zero-tolerance policy for women who exhibit regular ‘cheating’ behaviors in their relationships.
Note that there’s a difference between a woman who ‘cheated once’ back in the past as a bad choice, and women who exhibit regular patterns of cheating throughout their life and relationships.
If a woman seems to have learned her lesson and is now a loyal person—that’s good. If she still seems to be at a place in life where her attitude toward cheating is that it’s always a viable option for her—then you should probably avoid that situation and consider it a deal-breaker.
11. Life Stagnation
As a man, you likely know that you must continue to grow and develop yourself if you want to be more attractive, increase your dating marketplace value, and succeed at all of the vital metrics that matter in life.
And as a man who is committed to self-improvement, you should be looking for a partner who shares these same values.
Note that your partner doesn’t always need to be 100% the same as you in these respects. You may be a marathon runner and heavy weight lifter, while she may be more interested in yoga, meditation, and gentle ‘calisthenics’ at the park to stay in shape.
But that’s OK—because as long as you’re both oriented toward a life of self-improvement and you avoid dating people who are fine with just stagnating and not moving forward to further develop themselves in life—you should be on the right track to avoiding this red flag and setting yourself up for better dating success.
In other words, you want to avoid getting wrapped up in women who don’t level up their mind, soul, and body on a regular basis.
12. Toxic Communication Habits or Violent Tendencies
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Communication is key to making any quality relationship work.
Without it, you’re going to struggle to make any headway in your emotional relationship, intimate life, and basic forward-life momentum.
You could also put yourself in danger of building a home and a life with someone who isn’t equipped and committed to communicating with you in a positive, productive, and respectful manner.
Here are some toxic communication red flags to watch out for:
- Passive aggression
- An inability to be straightforward and to honestly speak her mind
- Negative or demeaning criticism
- Contempt (eye rolling, name-calling, mocking, etc.)
- Saying hurtful things
- Not understanding that words have power and that they should be controlled by the person speaking them
- Any signs of physical violence
Everyone sometimes makes mistakes. But these toxic communication habits won’t usually crop up unless the person has some deeply held communication/trust/behavior issues that haven’t been addressed.
So be very careful if you encounter any of them, and definitely consider them a red flag.
3 Red Flags in a Relationship With a Woman
In this section, we’re going to talk about some red flags that may not actually manifest until you get into a dating relationship with a woman.
But these red flags are still crucial to watch for, though they can be difficult to spot if you’re not aware of the constant need to watch out for them.
1. She’s Not Committed to the Goal of the Relationship
The goal of a relationship is for a man and a woman to join together in life, as a team, to start building their tribe and moving their family toward a place of greater success.
However, some people are not mature enough to see this as as good and noble purpose.
Does she still insist on keeping men from her past around? Does she vie for external validation by posting provocative pictures on social media of herself? These are not the signs of a woman who is invested in you and your combined tribe.
Some women don’t even think about the ‘goal’ of the relationship or how they can help to contribute to it in a big-picture sense—and that’s a classic hallmark sign that she’s not the kind of woman who’s ready to be in a serious relationship with a man who wants to build a flourishing future for himself and his family.
2. She’s Not Committed to Constructively Building a Future Together
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It takes hard work, effort, and commitment to effectively build a future together.
And this work will be physical, mental, emotional, financial, and even spiritual.
This might mean that the two of you will need to stop going out to the clubs and bars for dates—and instead, spend those evenings putting a new coat of paint on your rental property or working out together to get into shape and better your health.
These are the types of investments that grown-up couples make to better their lives and move forward together.
And the truth is that some women just aren’t ready for this kind of work.
So as a man, you should consider it a red flag if the woman you’re dating doesn’t seem ready for this kind of commitment to engage in the hard (but rewarding) work of constructing a successful future together with you.
3. She Fails to Show a Desire to Uphold Her Part of the Workload
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Some women like the idea of being in a relationship with a man who’s committed to excellence in life, but struggle to uphold their end of the bargain when the time comes to actually roll up their sleeves and get to work.
This is really a laziness issue—but even more than that, it’s a sign of wanting to ride on the coattails of someone who’s actually willing to put in the effort without being willing to meet them halfway as a true partner.
These types of women aren’t ready for a real relationship and should be vetted out.
You’ve Identified a Red Flag: What To Do Next
If you’ve started dating a woman and have noticed that she’s exhibiting some red-flag behaviors, here’s the general game plan that I’ve used to really assess the situation and make a firm decision without acting rashly.
- Take note of the behavior(s)
- Take your time (don’t escalate the relationship until you fully understand the situation)
- Keep her in your casual dating rotation for now
- If she continues to exhibit red flag behaviors, and/or if those behaviors end up causing you problems, drama, or chaos in your own life—you should disengage from dating this person and cut contact with them
- Continue to meet and date quality women applying the provenprinciples from our Dating and Masculinity Transformation System until you find someone who truly doesn’t exhibit any of the major red flags that we’ve listed in this post
- Don’t fall victim to the belief that you can change a woman, lead her to better behaviors, or ‘help’ her to eliminate red flags in her life
The truth is that most women don’t really want to change their behaviors. So the key is to find someone who’s already done the work to better themselves and overcome their own inner demons./
Launched in March 2023, this step-by-step system will teach you everything you need to know to ATTRACT the women you desire and KEEP them in your life. I'll share with you the exact strategies that I, and hundreds of my students have successfully applied to achieve true dating abundance as masculine men.
How Many Red Flags Is Too Many?
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This is a difficult question to answer definitively because, in reality, you get to decide what level of ‘toxic’ you’re willing to endure in your relationship in exchange for the benefits that the relationship gives you.
No human is perfect and completely devoid of issues.
With that being said, it’s been my opinion and belief in my own life that a strong presence of more than one red flag should be considered too many red flags.
If one red flag is present, you may be able to take a second look and make a cost-benefit analysis of how it might affect your life in the long run. But if there are two or more, you should consider it a deal-breaker for long-term commitment, especially if you’re working on yourself to be a truly high value man.
A few minor red-flag behaviors (often called orange flags) can probably be sorted out. But strong, predominant red flag behaviors are a big issue that can take years’ worth of therapy and self-work to unravel.
And as a man, you probably don’t want to invest in someone who isn’t already deeply embedded in that kind of self-improvement work anyway.
The truth of the matter is that the quality of the person you choose as your dating partner will have a major impact on the quality of your life.
This is a person you’re going to be sharing intimacy with. This is someone who’s going to sleep beside you, have access to your home, share resources with you, etc.
You need to be able to trust this person—and identifying red flags is the first step in determining if there are any ‘warning signs’ that you should be looking for that may indicate that you should pull back and start looking for someone different.
Finding a high-quality woman may seem like a challenge. But it’s totally worth it.
Go with grace, my friends, and never give up your power.
What is the meaning of a ‘walking red flag’?
When someone displays so many red flag behaviors that they would obviously be a problematic mate choice, they are commonly referred to as a ‘walking red flag.’
This is a lot like saying:
That person has so many red flags that it’s literally better to not even get involved with them to begin with.
What are the 5 green flags in a girl?
The 5 most important green flags to look for when dating a woman are the following:
1. She lives with intentionality
2. She’s willing to work hard
3. She’s loyal
4. She’s honest
5. She constantly strives to better herself