36 Dating Red Flags for Women and Men to Watch Out For

Rich Cooper from Entrepreneurs in Cars has re-released a chapter of one of his books that deals with red flags. It’s a genuinely intriguing list and it inspired me to do my own list, except, percentage-wise, my audience is more evenly split between men and women. So, rather than just doing a red flags list for men, it made sense to do one for women as well. In addition, since some things are red flags for either gender, there’s a list of those included too.

PS #1: I am differentiating here between “red flags” and “baggage.” I am treating “red flags” as a warning signal that you need to look out for and “baggage” as more obvious problems that you can see and take into account before going further.

For example, if the person you’re considering dating has $50,000 in debt, uncontrolled schizophrenia, or three children from previous marriages, anyone with half a brain can easily see the potential issues.

Some of the red flags may also seem obvious to a lot of us, but if a surprising number of people don’t seem to see the potential problem, it’s worth including. 

PS #2: A red flag is a significant warning that something may be wrong, and you should consider it carefully, but of course, some people ignore red flags and have everything work out fine. Are they the majority? Probably not, but they exist.

So, don’t look at one of these red flags as a sign that you need to immediately dump another person who has them, but DO take them into account. That goes double if you’re seeing multiple red flags.

Red Flags Women Should Watch Out for in Men

1) Overly emotional men: Whether it’s a man who flies off the handle or cries at the drop of a hat, it’s a bad sign. Men who show too much emotion are inherently unstable.

2) He seems threatened by your successes: Anyone who cares about you as a human being should be happy when you succeed or get recognition. If they don’t, it’s a sign that they’re jealous, have low self-esteem, don’t want you to succeed, or have some other unhealthy impulse going on.

3) Unreliable: How can you rely on a man to be your rock if you can’t even be sure he’s going to show up or that you can take him at his word?

4) He seems overly reliant and attached to his mother: It’s healthy for a man to love his mother, but he’s also not supposed to be enmeshed with her. If you ever start to feel like his mother is a significant impediment to your relationship or that there’s some kind of competition going on between the two of you for “her boy,” watch out. At best, he’s looking for a new “mom” and at worst, he will allow her to tank your relationship because you’re a threat.

5) Ignoring boundaries: Human beings have a natural tendency to push and test boundaries, which is fine. However, if you have firm boundaries in place and a man either just consistently ignores them or regularly tries to talk you into, guilt you into, or intimidate you into pushing past them, it’s a sign he may be narcissistic, doesn’t care about you very much, or just generally isn’t all that great of a human being.

6) Shiftless: A lazy man is going to drive you nuts a half dozen different ways. He’s not going to want to work, he’s going to leave stuff all over the place for you to pick up, and he’s going to put things off he told you he was going to do for long periods, maybe even for months.

7) He’s hit you or some other women: These leopards typically don’t change their spots. If they hit one girlfriend, they will hit the next. If they hit you once, they may pretend to reform when you threaten to leave them, but eventually, they’ll go back to it. You just do not need that in your life.

8) Overly controlling, including isolating you from friends and family: Some men like to set themselves up as the only person their woman can rely on to keep her under their thumb. If they can drive wedges between you and the people who were important in your life before he came along, like your family and friends, they can occupy that position by default. Guys like this are never the sort of men you want to be hooked up with long-term.

9) He doesn’t want to pick up the check on the first date: Picking up a check for a first dinner date is a pretty standard expectation in our society and if a man doesn’t want to do it, it either means he’s too poor to do so or alternately, he has some very unconventional views about dating. Either one is a sign that you should be cautious.

10) Very low effort: If you’ve made it clear that you like a man and he’s still putting no effort into you beyond potentially sleeping with you, it’s because he’s just not that into you.

Red Flags Men Should Watch for in Women

11) She’s a feminist: Modern feminism is not only hostile to men, it embraces a lot of beliefs that inevitably lead to conflict and the undermining of healthy, traditional relationships.

12) She’s really bad with money: If you get into a relationship with a woman who makes herself feel better by spending money and you’re not insanely wealthy – and maybe if you are – it’s likely to end very badly if you end up mingling finances with her.

13) Being any type of sex worker: Whether you’re talking about a prostitute, stripper, sugar baby, OnlyFans girl, or whatever, not only do you have to worry about the shame involved if your family or friends find out about it, but that type of work changes a woman. It tends to make them deeply cynical about men and often leads to them embracing a transactional view of relationships. It’s hard to build a castle with a girl when the foundation is made out of that kind of sand.

14) She’s an influencer: We could debate how popular an influencer a woman has to be to cause you to be cautious, but what you’re looking out for is an endless stream of men telling her she’s beautiful, sliding into her DMs, and promising her the world to get in her pants. How likely is she to hang in there when a relationship gets tough (and they all get tough sometimes) if she always feels like she has a half-dozen replacements ready to go in her DMs?

15) Women that need to be saved: Men have a natural tendency to want to protect and take care of women they care about. This can backfire though when a man gets in a relationship with a woman who has made a huge mess of her life and he tries to “save” her. If a woman is not a functional, together human being, trying to put her on your back and carry her to happiness is much more likely to pull you down than lift her up.

16) Referring to herself as a b*tch: You don’t want to be with a b*tch and if a woman flat out tells you that she’s a b*tch, take her at her word.

17) Drama queens/hissy fits: Women are more emotional than men and tend to generally enjoy drama more, so a little drama comes with the package. However, there are also women who have an outsized need for drama, even if they have to create it. These are the sort of women who seem to have contentious blow-ups with whoever happens to be around them on a semi-regular basis and if that person happens to be you, so be it. You don’t need that hassle.

18) Hot and cold/they flake: A woman who genuinely likes you is not going to leave you confused. If she’s hot and cold, flaking or generally leaving you unsure where you stand with her, it’s either because you’re one of several options or she’s just not that into you.

19) Being comfortable with other women doing extremely deceptive things to men: When a woman laughs off or worse yet, seems to perversely enjoy the idea of some woman taking a man to the cleaners in a divorce, tricking him into getting her pregnant, or making a false accusation, don’t walk, RUN in the opposite direction.

20) Doesn’t like children: Women instinctually like children. If you run into a woman who doesn’t, it’s a strong sign that you should be cautious because she’s damaged.

Red Flags EVERYONE Should Watch Out For

21) Way too clingy, way too fast: If someone is dropping “I love yous” a week in or planning out your whole summer on the first date (this really happened to me once), that’s a sign they have low self-esteem, are just very immature, or at least are extremely inexperienced. Be cautious.

22) They’ve gone to jail: Going to jail tells you three things about a person. The first is that they’re a criminal and have probably committed a lot of crimes because few people get caught the first time they break the law. The second is that they have a serious flaw. Since most criminals don’t get caught, they’re probably either dumb, unlucky, or have extremely poor impulse control. Last but not least, since they’ve been to jail there’s a good chance they have more than a few friends you don’t want in your life.

23) Over-the-top jealousy: A little jealousy is no big deal, but when you’re getting to the point where they’re falsely accusing you of cheating or picking fights with people for talking with you, it’s an unhealthy trait that is likely to lead to serious problems.

24) Frequent lying: If you spend a lot of time around someone and are smart enough to just let them talk and not immediately ask about every inconsistency, you may start to become aware of patterns of deception. People who lie a lot are obviously not people you want to tie yourself to over the long haul because if they’re lying to everyone else, they’re going to lie to you, too.

25) They don’t respect the opposite sex: There are people who, for whatever reason, just generally come across as disliking the opposite sex. Maybe they’re making nasty jokes about men or making it clear that they think “b*tches ain’t sh*t.” You may get a temporary reprieve because they’re crushing on you, but they are practically guaranteed to return to form when it comes to you if you give them long enough.

26) You find yourself walking on eggshells: We’re not talking about fights here, which happen to pretty much everyone on occasion, we’re talking about finding yourself being very careful about what you say and do because the least little mistake or non-mistake, depending on how they interpret it, is going to start a fight or get them in a bad mood.

27) Addicts: It doesn’t matter how wonderful someone may seem sober, if they have an addiction to a mood-altering substance, the odds of it taking them to a dark place or turning them into someone you’re not going to like over the long haul are very high.

28) External locus of control: People who blame everyone but themselves for the problems in their life will not only never succeed, they will also inevitably blame YOU for their failures if you end up together long-term.

29) Cheaters: People who cheat once are likely to cheat again one day, even if they end up long-term with the person they cheated with.

30) Your friends don’t like them: Don’t get me wrong – your friends are definitely not going to ALWAYS be right about your significant other and that goes double if you hang around with mentally unhealthy people. The flip side of that is your friends know you well, they tend to hear a lot of details, and especially early on, love can be blind. If your friends are sounding the alarm, maybe there’s a good reason.

31) Can’t hold a job: If they can’t hold a job, that’s a sign that there’s something wrong. Maybe they’re difficult, inconsistent, lazy, have mental health challenges, are secretly on drugs, are unstable, etc., etc. Let’s just say that this is a warning that there’s an area of concern somewhere.

32) Talks way too much about an ex: It doesn’t matter if they love an ex, hate an ex, or miss an ex, if they spend an inordinate amount of time talking about that ex, it’s a sign that there’s something significant still there and they are too emotionally attached to let it go. That’s not a healthy place to be if they’re trying to start a new relationship. 

33) Doesn’t fight fair in arguments: If they’re regularly dealing low blows that they know are sensitive for you when you get in a fight, that may mean they’re immature, love drama, or care more about “winning” the fight than solving the problem. That doesn’t bode well for the long-term health of your relationship.

34) You’re at different political extremes: Maybe it doesn’t matter all that much if either of you isn’t very political, but at this point, there is such an enormous gulf between liberals and conservatives on so many issues that it’s hard to see how they could date each other.

35) Divorced, especially multiple times: This may seem unfair because we all know great people who ended up getting a divorce that looked to primarily be the fault of the other partner. However, the statistics on this are daunting. 60% of second marriages and 70% of third marriages end in divorce.

36) They trash all their exes: How did that old saying go? “Once is an accident, twice is a coincidence, three times is a pattern.” Conceivably, anyone could have a really bad break-up with a horrible ex, but when there are multiple exes they’re bad-mouthing, the commonality is them.  

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