8 Red Flags That Should Send You Running From A Man


Are you tired of wasting your time on the wrong men? Listen to the story of two of my Love U clients – one too passive, one too picky – to discover the 8 things men say that should be instant dealbreakers. Want to save YEARS of your life? Listen to this Love U Podcast.

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Hi, I’m Evan Marc Katz, Dating Coach for Smart, Strong, Successful Women, and your personal trainer for love. Welcome to the Love U podcast. 

Stick around to the end to discover two of the most common patterns I see from women who remain single, as well as eight red flags to look for when you’re first dating a man. 

When we’re done, I’ll let you know how you could apply to Love U to create a passionate relationship that makes you feel safe, heard, and understood. 

So we’re going to get into it now and tell you a couple of stories, some killer metaphors, some stuff that you’re going to want to write down. So here we go. 

I want to talk about two former Love U clients. And I love these women dearly. And I want to frame this, that when I tell stories of people I do so to teach, not to tear down. I tell stories about me and my wife not to necessarily make myself look good, clearly, but I do so because it’s in service of trying to help. And so in telling the stories of these Love U clients, I want you to recognize that they’re anonymous. And I’m doing this for a greater good so that I can help you make better relationship choices with men. 

So despite my affection and admiration for these clients, it’s pretty obvious to me why they remain single in their 40s. First, we’ll start with Elise. Elise is, let’s see in my world where I teach women that you’re the CEO of your love life, Elise is a perpetual intern. She’s really sweet. She’s super cool. She comes from a place of pure feminine energy. She really responds to confident guys, big brains. She’s got to, she certainly has a type. She hasn’t had much success with men because her default setting is to be a pleaser who wants to win over a guy. She sometimes bends over backward to please. And she’s operating from a place of scarcity because she doesn’t have a good track record because she’s in her mid-40s and average looking. Sorry, not everybody can be a supermodel. For these reasons, she doesn’t always believe that she deserves more. And so she settles for less. Ask yourself if he’d ever done the same thing. Not feeling terribly confident, not having a great track record with men, and then suddenly start seeing some guy who you’re attracted to with a big brain starts paying attention to you and you’re like, “well, I guess this is as good as I can get.” And my client, at least, drops everything when she meets a guy that she likes because she’s spent her whole life looking for love. The last instance I experienced with her. She moved for a guy. She dropped her life here in L.A. and she ends up fighting for a relationship that’s not even worth fighting for. That’s the crazy part. So there’s this long-shot candidate. He’s a divorced guy. He’s got a troubled son. And she moves to be with him and steps into his world after a few months of long-distance dating and discovered, quite quickly, that it’s very different being in a long-distance relationship where you could talk and flirt and put in a little effort and get a lot of rewards. Then to be a day to day partner living in the same house with a person who’s not happy, who’s got a troubled relationship with his son. And she’s coming in as a stepmom. And she doesn’t really respect the way he’s doing things. It’s like this whole chaotic thing that she decides to take on herself and she holds on for two years. 

Gosh, I love Elise. And it’s really hard to watch this since it shows the limits of my control as a dating coach. All I could do is give advice and say, don’t do that. Don’t go there. Cut this off, set some boundaries. Have some self-esteem. Operate from a place of competence and abundance. Say no to things that aren’t working for you where it doesn’t feel good. 

So I want to contrast Elise, the perpetual intern who gives the man control of things with another client of mine, her name is Sherry and Sherry has embraced her CEO energy, which is, in general, a good thing because it means you won’t settle for less. But Sherry takes it too far. She’s objectively too picky. And when she makes her choices. They’re like these deep subconscious choices. She’s not even thinking about what she’s doing. She’s just taking these long shot, Hail Mary picks. And the only way that could work is if the sun and the moon and the stars all align at the same time. That’s the only way Sherry’s ever gonna get married unless she changes her ways. 

So on the surface, you might be Sherry. And then there’s no judgment. And this is like a tale of two clients. I’ve got, you know, Elise, the intern over here, and I got Sherry, the CEO over here. She doesn’t have high enough standards and her standards are so impossibly high that it becomes impossible for her to succeed. 

So she’s bright. She’s attractive for her age. She wants to have kids even though she’s in her early 40s. And she’s always going to attract a lot of people because she’s objectively a catch. But Sherry has even greater problems to some degree than Elise does. If Elise lacks self-esteem, Sherry has some major blindspots, fatal blindspots, not the least of which is that she thinks she’s 100 percent self-aware. She thinks she understands everything. 

So when I give her advice, she almost never follows it. She uses her own instincts, not recognizing that those instincts are what has led her to be forty-three, single, and childless. And so there’s no judgment. And, this is for all my clients. There’s no judgment. But why would you hire a coach if you’re not going to take some of what he says under advisement instead of “yeah, I hear you. But I’m just going to do my own thing.” 

So Sherry’s issue is that in no particular order, I wrote a couple of things down. She’s looking for the opposite sex version of herself. I’m familiar with this because I’m a lot like that, was a lot like that when I was single. I wanted to date East Coast, Jewish, liberal, intellectual, good work ethic, sarcasm, whatever the hell that makes me me. I find that familiar. I find that attractive. And I was always drawn towards it. And I didn’t recognize for about ten years that trying to date the female version of myself was a losing strategy. 

So Sherry dates in that manner, wants to date herself the male version of herself, but without her own flaws. Which brings me to share this second problem. She doesn’t recognize her own flaws, and that’s hard. And I use myself here because I think it’s easier if my flaw is that I am opinionated and a know-it-all and sometimes arrogant, anything anybody could say about me, I’ve heard it a million times before. And if those are my flaws and therefore I’m pretty difficult because I have opinions about everything and I micromanage situations and I micromanage at work and I micromanage in my relationship. I could at least take ownership of that and be like, “you’re right. I have to step off. I have to soften that.” I’m not going to insist that someone who feels that way about me is wrong. They’re right.

The problem is a lot of people have a hard time admitting what their faults are. So it’s very easy to see someone else’s faults in yourself. And that’s what Sherry does all the time. She points the finger at other people. Never really recognizes, never looks in the mirror, and recognizes how she is equally complicit in why she’s single. It’s not just everybody else’s fault and everybody else is flawed. Because I can hand Sherry a husband and she’d still find 100 things wrong with. Which things can you and can’t you compromise? And Sherry hasn’t figured out the art of compromise yet. She refuses to compromise, even though she compromises in her career. She compromises on her home, she compromises with her family and her friends. But she won’t compromise in this area. That’s probably its own Love U podcast – “How one should compromise.” 

Finally, Sherry takes huge and terrible risks in love. Again, I present this to you because maybe you’re familiar. You chase excitement instead of comfort. Now again, comfort doesn’t mean you’re with a guy who kisses like your brother. Comfort just means it’s easy. It’s smooth. It has this really organic path. When you’re chasing excitement, you’re banking on the long shot. Overvaluing that instead of the smooth ride. So we’re spending a lot of time on hope, fantasy, and potential. What are examples of this moving in with someone after a month, going on a three-day cross-country date, looking in other countries for love, developing full relationships by text? And so it looks perfect. That’s exciting. But it’s a self-fulfilling prophecy. It’s really safe to do to fall in love with a guy in another country. It’s really safe to fall in love with a guy in another state. It’s really safe to fall in love with the guy who’s got a wife because it never works. It’s built-in. It’s never going to work. 

So I want to borrow a metaphor from Love U because I think it’s useful. And I share with you that the eight red flags that I promised at the beginning of the video because there’s a lot of ways that one can get rich in life. You could save a dollar a day in your piggy bank. You could start a 401K when you’re 21. You can work your way up from the mailroom at some company. Right. You can take over or expand a family business. You can work side by side with some genius entrepreneur. You could start your own company. You can invest wisely in stocks and real estate. It’s all viable paths to get rich and build wealth by the time you’re ready to retire. OR you can buy a lottery ticket. Now, a lottery ticket is the fastest way to riches. But it’s the one with the least control and the highest failure rate because the lottery is the fast path. It’s no work. There’s no thought behind it. It relies on luck. 

I don’t like luck as a strategy. That’s what I’m here to share with you. There are better ways to date. Dating is a skill set. Relationships are a skill set. It’s not just something that you come by because you’re human. Just like anything in life, playing guitar or computer programming, or getting along in corporate America, there’s a skill involved in this. 

So as a dating coach for smart, strong, successful women, I see myself as your risk manager. What are the chances that this investment is going to go south? And why would you make an investment if it has a very, very low percentage chance of paying off? So I am risk-averse when it comes to love on behalf of my clients. 

And here are eight red flags that you should pay attention to and write down that I wouldn’t even embark on a relationship. I wouldn’t even go on a first date in these situations. 

Number 1, long distance. 

Number 2, he’s separated. 

Number 3, recently divorced. Like, the ink is still drying. And he hasn’t had a relationship since his divorce. 

Number 4, he’s got current addiction problems. 

Number 5, he’s got current employment problems. 

Number 6, he says he’s going through a weird time and he doesn’t know what he wants. 

Number 7, he thinks you’re too good for him. 

Number 8, he says he doesn’t know if he ever wants to get married or if he wants to have kids. 

I am positive you have and continue to take a chance on guys like this. You see something in his profile. Have a conversation. You hit it off. He’s cute. He’s smart. He’s interested. And then these things that we just read off, we throw him out. We discount them. We pretend that these things don’t matter. Other than this is going to come up somehow down the road and it’s going to come back to bite me because it always does. So why even get started? 

I’ve got a quickie anecdote and it’s a client of mine. She was in Love U five years ago, and I adore her. And I’m not going to mention her by name. But she joined the course. She was in her late 40s and never married. And through the work in Love U, you learned how she should be treated by a man, raised her standards in such a way that she never had a better relationship in her life. And as she graduated the course, I remember her telling me she was seeing a guy who was really, really good to her. He was a good guy and he made her feel safe, heard, and understood, and all the other things we talk about and in Love U. But this guy was suffering from a certain kidney disease, and he had one of his kidneys removed and he had circulation problems. And because of his circulation problems, he had the bottom of one of his legs amputated. And because he had all these health problems, he was depressed. And because he was depressed, he was taking antidepressants. And because he was taking antidepressants, he had erectile dysfunction, which is affecting their love life. And my client was explaining to me that she really loved this guy. She really loved how he made her feel and how he treated her. But it was hard because he was facing all these issues. And I remember saying to her point-blank, again, forgive me for being insensitive. “Jessica, I promise you, you can find a guy with two kidneys, two legs, and a working penis who is good and treats you well.” And that strangely crude statement gave her some relief. She treated him as if this was it. It was the first guy who’s ever treated me well, but he’s got all these problems. These problems are really hurting our relationship. And she thought that was the highest she can go. I said, “no, you can get all the good treatment with a guy who doesn’t have these problems. 

And so extrapolate that you could have a great relationship with a guy who is in your city. You can have a great relationship with a guy who isn’t recently divorced. You can have a great relationship with a guy who does know that he wants to get married and have kids. The idea that you have to accept these things in men is just not true.” 

So if you continue to take a chance on these long shot guys with these major obstacles to overcome, just because you’ve got chemistry and excitement and now by paying attention to those red flags and eliminating the 90 percent of the guys who run afoul of those red flags, now you can focus your attention on the 10 percent that actually have a chance of working out. That is the Love U way. 

Thank you for your time. My name’s Evan Marc Katz. I appreciate you tuning into the Love U Podcast. 

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And if you want to find love right now and are committed to making healthier choices with men so you can have that easy relationship that makes you feel safe, heard, and understood look for the link below and apply for coaching with me in Love U. 

Talk to you soon. 

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Join our conversation (17 Comments).
Click Here To Leave Your Comment Below.


  1. 1

    Oh my goodness… I’ve been listening to your blogs Evan for years and bought a few programs along the way and yet I still had a light bulb moment from this podcast! Don’t date someone who is separated or recently divorced… how did I miss this! You’re podcasts are THE BEST and I ALWAYS take something away from them and they keep me going on the right path and in the right direction. I would have signed up for the one on one coaching, but I’m based in Australia so it doesn’t work. Hugs to you for your amazing advice which I fully respect, especially because you are happily married and not single like a lot of the coaches out there xo

  2. 2
    Julia Arango

    I agree with all except #1 and ,#5. Long distance relationships are not ideal, but thanks to planes and trains can be done. If you break up he isn,t in your neighborhood! If you marry, one of you can move. I moved to California for a boyfriend. We broke up, but I am so glad I moved there. I stayed 9: years and left only because of a job offer. As for current employment issues, we,ve all been there. I still bitterly resent guys who didn,t want to date me when I was unemployed and people who didn,t want to set me up with guys for that reason. Anyway, we are in pandemic times. Show me someone who doesn,t have employment or money problems!

  3. 3

    That is: I agree with Julia Arango on # 1.

  4. 4

    The list, to me, is a no brainer. I can’t understand why anyone would ever consider dating anyone who falls in that list. They’re instant dismissals.

    What I have a problem with is the assumption that a woman has all these options. As Evan says, a woman can only chose among men who are interested in her. And most average women (and just about all below average women), especially over 35, don’t have all that many options.

    Rule out the eight listed above, hard drugs, alcoholics, people miserable with life, and men as old or even older than her father, and the list gets rather narrow, if anyone is left at all. That’s before any of her preferences even come into play. So I can see why she would settle for that amputee, although he seems to fall somewhat into the miserable with life category. But at least he didn’t also have one or more of the other major no-nos, and she claims he actually treated her well..

    Now, reasonably attractive women will have better chances. And yes, I can see how pickiness can easily get in the way for more attractive ones.

    I agree that the “trying too hard to please” or “settling too much” thing comes from a view of scarcity. But I also think that the feeling of scarcity is often rooted in reality.

    1. 4.1

      It depends where you live re choice (over 35 or under). I am nice looking in a sea of attractive women in my city. It took a lot of dating but i realized the harder i worked at establishing quality connections online, the more choices in dating i had and potential high quality matches. More than when I was way younger! So you can definitely, within reason, be selective as long as you live within a metropolitan area.

      I do agree though that it helps to take a nuanced view of the big 8 and to keep an open mind. A friend of mine is a recovering alcoholic, he’s in a very happy relationship. I have employment issues due to illness and pandemic, boyfriend and i are super happy together.
      People having weird times is a part of life, doesn’t make them undateable. It’s if the issue seems to be a permanent fixture, that it’s going to be highly problematic. Which is why i always think it should be called investigative research rather than dating, though i understand this doesn’t sound romantic.

      1. 4.1.1

        EMK will also be the first to recognize that there are exceptions to nearly every one of the LoveU rules and guidelines. So to your point Malika, as a 51 year old woman in a high cost of living area where desirable men in my age range can and do date much younger, someone else’s no-way-in-hell might be perfectly satisfactory to me if I truly want a relationship and I am realistic about my options.

  5. 5

    Agree with many of the commenters on #1. If you live in a rural area, there likely will be few/no available men with whom you’re compatible. I’d add unresolved mental health issues and widowers who haven’t given themselves enough time to grieve (varies a lot with the person) before dating again.
    The sad thing is that some of these may not be sussed out right away leading to much wasted time.

    1. 5.1
      Evan Marc Katz

      The list was about things you can tell right away. There are a million and one other dealbreakers that can arise later.

    2. 5.2

      The widower one is worth discussing. I went out with a man whose wife had died more than 10 years prior. We had three dates and several phone calls. He still referred to her as his “wife” (present tense), and said that she was the most perfect woman he had ever met. He spoke about her often. I realized that he was still in love with her and that no woman would ever be able to compete with this perfect version of his deceased wife. My third date was my last. 🙂

  6. 6

    This is also one of my favorite entries. It made me think. I enjoy hearing about other women’s experiences.

  7. 7

    The long-distance thing is tough. I’ve tried it twice and it hasn’t worked out for me, but I would give it a shot for the right person. I have a good friend who dated a guy in Florida while she lived in New Jersey. After a year, she moved to Florida to be with him, and a year and a half later, they were married.

    I live in a big city where dating in the suburbs feels like long-distance. Due to traffic, someone who lives in the suburbs may take a 90-minute to two hour drive. So you end up hauling a suitcase back and forth every weekend. I have many girlfriends who won’t date a guy in the suburbs because it’s too inconvenient. That said, I have one friend who gave a long-distance guy in the burbs a chance and ended up marrying him two years later. 🙂

    I guess there are exceptions to every point Evan listed and I understand that Evan is just presenting scenarios that are less likely to work. For me, I have no kids and no pets and can work from anywhere, so the long-distance thing seems like it could be possible in finding the love of my life. I do draw the line at dating someone in another country.

  8. 8

    Funny this. All of my adult life I made far and away more money than the women I came to know and had relations with–except for two who were born into very well monied families and had or would have millions of their own. Neither had any independent earning power though. I married the first one one year out of college and regretted it and moved on before there were children. The second one got pregnant and I married her for that reason and ended up a single father. Their money and any perceived lack of my own was not the issue. At least 50% of the people I have known in life had inherited wealth–and I mean wealth such that they could live the 1% lifestyle without working. No–money was not the issue with them–other than that they did not have enough of a challenge in life and being close to someone who took the world head on and did so without fear and with delight was overwhelming for them. If you can buy a Porsche at age 28 and pay it off in six months, you make a lot of money–I did.

    People who chase money for its own sake or people who marry for money are asking for their own special set of problems. And, you usually get what you deserve. I am no longer young, so my views have changed. I ended up raising 3 of four 4 children on my own as a single father. The 4th child dying just days before her 4th birthday is what brought on the divorce. I am, for the most part, quite satisfied with the job I did. I gave up looking for or finding someone who would fit into all of that and not be demanding beyond what I think is normal for an adult. As an adult, you ought to be able to take care of yourself, regardless of gender. If you can’t and you need someone else to fill holes in yourself or your life, you are doomed to failure. Those women above have massive holes in themselves–pretty obvious to me.

    I will leave you with what my father said to me when I was 19. My father grew up in a home with servants–maid and butler, cook, housekeeper, etc. He came from old money and there exists today a life size bronze statue of him in his surrogate hometown.

    “All money does is buy you a bigger house and a nicer car–it does not and cannot buy or bring you happiness”. He knew from which he spoke.

    All of which is to say, is that if you are lucky enough to find happiness in your own right, you will not
    need nor find the need for the trappings associated with wealth. Easy enough, perhaps, for me to say given how much I have on a personal level both in terms of children and material things. But–it was the children who brought the immense joy–and pain, not the success or money or anything else like that. I love my children and they love me. My youngest has now turned 16 and will soon be leaving for college. Were am I headed? Well, I will sell my very desirable largish home in a very, very upscale area and move to the “country” where I can sit on my porch of a summer’s evening, have a cocktail, pet the dog and cat, watch the sun set in the west and smell the wonderful scent of new mown hay. If someone should happen to come along and entice me with her scent, presence and sense of self, well, she can sit next to me and also enjoy that sunset.

  9. 9

    I had a problem understanding No. 7 where he thinks your too good for him. Would that not make him work harder to keep you in his life?

    1. 9.1

      There’s a difference between a man thinking you’re good for him versus him thinking that YOU think you’re too good for him.

      The thing is, at some point men don’t want to have to work to keep you in their life. We want a woman who very much wants to be there on her own. And maybe work a little bit herself to keep the man there. That’s what the men here are trying to tell the women on recent comments on this site. Women are saying that they know men are interested when men text or contact them. It shows interest and confidence. But those same women fail to realize….the fact that they aren’t doing the same….what should that show the men about themselves? Why are men the only ones supposed to do the legwork?

      We don’t mind doing a bit of the legwork for a little while, but after a while the guy doesn’t want his relationship to be about working to keep the ever-slipping interest of an ambivalent woman.

  10. 10

    Having just recently broke up a man going through a divorce, I completely agree with #2 and #3. I thought this man was pretty stable, even though his divorce wasn’t final. Then his ex, who I knew professionally years ago, found out we were dating and made our situation difficult. She had even moved on herself with a new man. I have somewhat of a public job, so she’d criticize everything I said/wrote and berated her ex often. They have a very toxic relationship, but to their friends always looked like the perfect couple/best friends. And he never stood up to her. I think she wanted the new man plus to have the old one handy at all times.

    So I called it quits. Please don’t ignore those flags.

  11. 11

    I am pretty puzzled about the #8.
    I am following your blog for months and have learned that you are a pro marriage and pro kids person, but does it mean that those who do not automatically are some outcasts of the society?
    I know that the social norm was and still is Marriage and kids, but a person who openly admits that he does not want kids and wants to focus on the relationship instead is regarded as unacceptable?
    And by marriage i hope you mean any kind of official commitment. What, if i do not want to marry you and i want a “civil union” instead, does it mean that i love you less?

    It’s common sense in my opinion. Ah, if one of you wants marriage and kids and the man says ” I don’t know let’s wait” while knowing perfectly that he will never marry/have kids, yes, i find that unacceptable. But i don’t find nothing wrong with a man that says openly and honestly before going exclusive that he might not have kids and if the girl wants for sure kids it may be better for her to look another place. They just have different life views.
    Or maybe I am crazy indeed and there are no people who do not want traditional marriage and kids and i am just searching in vain.

    1. 11.1
      Evan Marc Katz

      Thanks for the comment, Andi. Briefly, you’re taking something personally that isn’t inherently personal and putting words in my mouth that I didn’t say.

      a. No one said those who don’t want marriage are outcasts.
      b. No one said that your personal choices are unacceptable.

      However, my clients come to me because THEY WANT to get married. And if THEY want to get married, then it is, indeed, common sense to steer them away from men who don’t want to get married.

      If what you’re doing is working for you, keep doing it, but don’t get pissed at me from telling my clients to stay away from guys like you who have different life goals.

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