Dating An Insecure Man: Why It Just Won’t Work

August 10, 2012  |  

My last dating situation was probably one of the worst. In the past I have dealt with a cheating ex who tried to justify his doggish behavior.  Honestly I didn’t think any relationship, past or future, could get any worse than that until a few months ago when I dated an insecure man.

Chris* looked good on paper. He was intelligent, ambitious, and had a promising career that paid him extremely well. He had great conversation, opened doors, was considerate, and liked to talk about feelings. I soon learned that even I, as a woman, didn’t like talking about feelings as much as he did. Probably because his feelings were accusations targeted towards me.

He snooped my Facebook page (yes, this grown man), interrogated me about childhood guy friends, and even questioned my ‘feelings’ when I didn’t respond back to his calls in what he considered a reasonable amount of time. According to him, I didn’t show that I cared enough and every guy besides him was the person I really wanted to be with.

The first time the jealous accusations occurred I shook them off, partly flattered that he didn’t mind showing he cared. Silly, I know. But the second time when he stalked my Facebook wall picking out posts from guys who had written me before he and I even began dating, I knew I wasn’t in a healthy situation.

After this, our relationship went downhill. If I made a nice comment about another man, he said I didn’t compliment him enough. If I talked about guy coworkers in an innocent manner, he questioned my relationship with them. And if I didn’t answer the phone when he called, he immediately accused me of cheating. These accusations came in the form of long text messages telling me how inconsiderate I was and how I didn’t make him feel wanted.

Insecure men come in all disguises, but most share the common traits of appearing sensitive and caring. To most women a caring man who listens is a hot commodity; but it quickly changes when his insecure traits take over the relationship.

In the article “Is It Love, Or Insecurity?” psychologist Joseph Nowenski, highlights some traits of an insecure man. These include a need for constant reassurance and approval, distrustful, smothering behavior (basically he wants to be with you all day, everyday). In addition, most insecure men are jealous or possessive.

Chris possessed all of these traits. And while I shunned them off initially, it didn’t’ take long to realize his caring and sensitive ways were partly due to him being insecure. A caring man is something that I wanted, but an insecure man, not so much.

This scary excuse of a relationship lasted about three months before I realized that my nerves and sanity were at stake because of his lack of trust and enormous level of insecurity. He accused me so much at times I almost thought I was cheating. I ended the relationship quickly, but not without learning a valuable lesson. Dating an insecure man, especially one who doesn’t consider himself insecure, is like watching a relationship die a slow, painful death. Basically, it just won’t work. Dating an insecure man is like saying “nerves, I don’t care about you and sanity, I don’t need you in my life.”

According to Nowenski, dating an insecure man is like a bottomless pit that might just drain you of every drop of love you possess. My translation: dating an insecure man can drive you crazy.

While most people possess some level of insecurity, problems arise when a person’s level of insecurity affects the majority of the relationship. You  can tell an insecure man you love him, but he questions why. You may say that you’re tired and would like to go to sleep. He assumes you’re just not attracted to him anymore. Nothing you can say or do will make an excessively insecure man, secure. It’s a waste of time, effort, and energy. And normally the person who ends up drained, will be you.

From my last situation, I quickly learned that everything else could be great about a man; but insecurity will more than likely overshadow it all.

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  • Egodeath Godmaster

    The lack of compassion and empathy coming from posters (and also the OP) is disappointing, to say the least. After my first love broke my heart, destroyed my self esteem, and strung me along for crumbs of affection for over 2 years, I took that baggage with me into my next relationship. (I didn’t realize it would be an issue until the relationship began.) I would say that in many ways I am a deeply insecure person, but I do my best to keep it in check. I have never checked my partner’s phone, stalked them on FB, accused them of cheating, etc. They do their best to reassure me, but I know that my issues can be draining. Thankfully I have a partner that is willing to work on my issues with me and not abandon me because of my insecurities.

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  • Dan Williams

    I’ll tell you honestly, I was a bit like that person you were with, but it was because I had been betrayed in the worst way by my first love of five years. It was another five years before I could be in any kind of serious relationship at all with a woman, and I was very fortunate to find someone I felt I could trust. We’ve been married for twenty years now, and I’ve never felt more secure in a relationship than I have in ALL of those years. Not once have I felt any concern over faithfulness. How can this be? Simple: she brings my name into conversations frequently, letting everyone know how significant I am to her life. I do the same for her. There has never, ever been any question but that our relationship is one that can not be trespassed upon by anyone under any circumstances. When people think of me or her, they think of US.

    It’s hard to find someone like that, but it’s so worth it. People who claim to love each other, and then go off by themselves with nothing other than a ring on their finger to indicate that they are in a relationship, convey an independence that is non-conducive to a healthy relationship, in my opinion. Any meaningful relationship with the opposite sex, other than your significant other, should involve fully your significant other, or that relationship is unhealthy, period.

    My wife saved me from a miserable life of frightened loneliness, and I love her dearly.

    • Jerry

      All the women on here talk about these men like defects. Too a degree, yes they are defective. But guarantee these same women end up with worse. Every man will have some issues. And these same women will eventually exploit them and post about that issue on some forum. All the while pushing 40, convincing themselves that being alone is ok. Insecurity is not good in general, but are you on FB 24/7. Do you try to have a committed relationship and put FB activities, and friends above that man? Do you live your life out on FB (ie. your life from the last 10 years can be viewed for the last 10 years)? Do you still have an over abundance of male friends? Well if you meet a man with trust issues from a past relationship, don’t throw him right into your social fire where trust is his only means security. Of course there is a honeymoon period. But a month or 2 in if you are feeling it then fade back from the social scene and focus on that. If having a life partner and love is your priority then act like it. If the love is worth it, go for it. If not, break it early. But know that insecurity, especially from past experiences, can be fixed. It takes a woman that wants to stay. With that said, it takes years to repair. Wont disappear in a month. If he is worth loving, work to fix it. Insecurity issues dont disappear by just saying you love a woman so you surpress those insecurities. Trust is the problem. With an insecure male, his trust has been stomped from some past relationship where he did trust. Ladies, if your out there looking you need to consider that. Trust is earned. If he genuinely feels that, you can create a life partner. Recurrences subside and then you have the “almost” perfect man you always been wanting.

  • Kate

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  • Kate , thank you so very much for helping with the custom spell. I don’t know what you did to help me land the job of my dreams and the love of my life but it worked. It was nothing short of a miracle. I would love to be able to repay you not only in dollars but in extraordinary kindness & love. Thank you so much

  • bridget

    I used to think magick was bogus but after Martin left me I felt open-minded to try it. Maybe I was desperate too. But this is real! You restored the love we had for each other. And now he proposed as you promised he would! I am your friend forever and very grateful for all of this. I will come back again, very soon. thank u

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  • Michelle

    I married one. IT WAS HELL. I moved overseas to be with him, thinking that distance was the source of our problems. NO. BIG MISTAKE. 4 months later and 20 weeks pregnant, I was on a plane home.

  • Tlb

    It is so true that insecure extremely jealous men come off as the most romantic, caring, passionate, loving man. Beware it is just a fake facade to get you hopelessly in love with them so when they start shedding the fake mask and their true scary selves comes out, u will be hooked and in total disbelief that they could be so cold blooded liars. They are nothing but malicious liars so full of hatred for woman, they will make your life a miserable nightmare. They know they are sick but continuously go searching for victims. They also can be labeled as narcistic sociopaths. Be happy when you find the courage to leave for good. There are so many better men out there and that’s what they truly know deep down. I fell for one of these guys for 4 yrs, thought he was my soulmate but finally realized he was a cell mate. I left and found a truly genuinely nice guy.

    • Rob

      Salty much.
      I’m caring, passionate, very loving and nowhere near insecure. I love women, and my ex, with not one shred of malice. Sounds like you’re still recovering from some scars.

  • Juliet

    Your love spell has huge powers! I cant believe what’s happening to me! It’s been only 1 week since you did that spell and Joe is already after me. Since the last week-end he phoned at least 7 times. I believe he seems to realize his mistakes. It’s absolutely happening as you said!! Thank you! Your work is helping me so much… Without you I would feel so lonely and miserable… Thank you!

  • Sydney

    I am currently in a relationship with a man that I believe is insecure, yet still am happy. Yes he may be insecure, but he loves me like no other. Yes he can be controlling in certain aspects, but he does so for my safety. Although during the initial stages of the relationship I wanted to leave and ran as far as possible, but I am glad I didn’t. Communication and trust can be built ladies and it crucial in any relationship. He tells me about his concerns, and I mine and we reach an agreement and common ground. We have the power to make them secure, reinforce your love for him, appreciate and respect him. I understand that these ‘clingy an obsessive’ traits may not be appealing to every woman, but one should confront him about it. If he is willing to change he will.

  • Sil

    I was in for 10 years with an insecure man. He is controlling and stalked and snooped. When I met him, I was so attracted to him physically that I didn’t pay attention to who he truly was. I ended up pregnant after about 4 months of dating. I even knew early on that he was bad news, but I didn’t listen to that gut instinct. I decided to make it work and went through the worst roller coaster ride I could have ever imagined. Always trying to adjust my reactions to how he would feel about things, I ended up losing myself. I have been fighting back for two years now and have finally gotten out on my own, but its so tough. I miss writing. I used to write in journals before I met him, but even those weren’t off limits for him. I even started to write things a certain way knowing he’d read them. The last straw was him picking up my phone for probably the 100th time and I just lost it. No matter how far in our marriage I thought we had gotten, he would make me realize how far we weren’t. My relationship of 10years before that was nothing but cheating. Although, he let me be myself. My marriage was incarceration! It was a unbarred jail cell where I had to walk the walk and talk the talk in order to just make it through until bed time. I wasted so much of my life with this man and have nothing but regret. I’m hoping I can break free completely soon. Just waiting on some signed papers, but it is hard. The roller coaster isn’t gone completely and I have moments of wishing things were different. I want to start dating in order to move on, but I don’t trust myself with another man. I don’t think I have the skills to know if he’s worth it. Trust is gone. I’ve basically become a shell of a person.
    Insecure men will break you. Although he wasn’t physically abusive, he was loud and controlling in different ways so it almost feels like I was. I don’t even know if this makes sense. It’s just a mess.

  • syleishere

    Reading this article I would have to say it is to 1 sided. I have heard women say these types of things way to many times to know there is something she is hiding. Even insecure guys can be secure if the woman is not doing anything to make them feel insecure to begin with. A woman who actually cared about a man, would also seek counseling for this person instead of leaving him flat on his face, that is what people who love each other do. I believe the writer could possibly be the insecure person and make her partner into a codependant sharing the same traits. I would have to ask if someone is snooping email or facebook, that you must have done something to make him feel jealous or betrayed him in some way or he really does need counselling since this is not normal behavior. I have dated enough women to know right away when a woman starts accusing someone of being insecure/jealous type, they are generally the ones with the insecurities and cover them by blaming their partners. I think we need a reply from the man at this point to his defence on the issue to give a good analysis. The last point that does not make sense in this, is with my phone or facebook, I could care less if my partner was reading my things, so what is she hiding…

  • Dan

    I’m sorry but the rationale a lot of you ladies give is just mind blowing. A lot of you need to look in the mirror and ask yourselves why you are ending up with guys that do this because I’m sure you’re not all perfect angels and are giving these guys some reasonable doubt about your intentions in the relationship. I dated a girl for 5 months who constantly told lies but I believed her out of blind hope. I friended her on Facebook and from time to time she would get tagged with a guy named Alex at a movie or a fest. I would question her and she would tell me that it was a friend and she was there with other friends too. Turns out it was her ex boyfriend and she was cheating. I was suspicious throughout the whole relationship because deep down I knew the truth. I did Facebook “stalk” (as if thats even such a thing..anything is public knowledge on Facebook) her because she gave me a reason to suspect she was up to no good, and surprise, surprise …she was indeed up to no good. So before you go and criticize all men, you should look at your own behaviors. I’m not saying there aren’t some psycho guys out there, but a lot if times it’s you women who make us this way. It isn’t being a guy in today’s world..especially when it comes to dating. Especially because of Facebook. If you’re in a relationship you shouldn’t be commented how good a guy looks, or going to dinner with guy “friends”. Honestly some of you just need to grow up and stop blaming men for everything.

    • allwomenarejealous

      yep..5 years of my loving angel manipulating, lying and playing the Im never wrong game….. after the lies I question why…. but I was always the insecure and jealous…. turns out she would call her ex then call me just to erase the redial info….. she was crazy…. ill believe an honest woman who doesn’t flirt.lie.or cheat exists when I meet

      • Dan Williams

        I married one, but they are RARE. The problem is, too many men pass on the quiet types. Look for the wallflower, bro — they are late bloomers, and as the young beauties age and get angry and ugly, your wallflower will become a rose. Just remember when you find her, you stay LOYAL to her. She will deserve it.

  • humanizer

    This guys sounds a little over the top. I dated a woman who was just as insecure…she went through all my stuff, not really sure what she was looking for. But to be honest you all sound a little mean…and reek of a double standard. Sure you want your man to be honest and caring, but if you treat men like sh*t, the secure ones will leave you and if they have any insecurity at all, you will be bringing a world of pain onto them and yourself. Read the book “Attached”…

  • Guest

    I swear when I finished reading this article I wondered had I started dating “Chris” right after this 3 month relationship ended. Unfortunately, I ignored the signs and started to believe I had the problem. Now I’m engaged and pregnant to “Chris”.

  • Lostmyfriend

    I’m pretty sure my sister in law has hooked up with this same kind of man. She left a 24yr marriage to go be with this freak. Im sure he was real attentive,loving, smooth talking, and extremely charming. HE promised her the world and his love and even wants to marry her all within the 6 months she was cheating with him. NOw that she has left and is living with him, she has NO contact with any family or friends and barely even calls her 18yro daughter or mother for that fact. Its like she just walked out of her own life and left everyone who loved and cared for her behind. SHe has abandoned everyone to be with this man. I call it crazy. She has made reference to how jealous and insecure he was. I fear for her safety, but she will not talk to anyone. I think he has cut her off from those that love her and is holding her hostage. Is there anything we can do to get through to her.

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  • Eboni

    This is so true. Please ladies run when you meet men with these traits! There’s something wrong! http://www.singleplusdating/free-report/

  • MLS2698

    Ha! My ex-husband once started looking in a hanging flower pot we had in our tiny apartment when we first got married; claimed that I may have put a phone # of a man there ( huh?). After I finished cursing him out, he stated that he had aunts (his mama too, but he didn’t want to acknowledge it) who always cheated, and thought I was doing the same. I explained that I could care less about what those BISHES did, and he needs to check himself. It took about seven years for him to stop being jealous; and here is the catch: he ended up cheating years later…..must be genetic.

  • Erika

    OMG! I went through this and it was CRAZY! We were on and off for about 3 years. Oh wait… theres more… He was my first and I ended up having a baby by him. My son is now almost 6 and he is a deadbeat and STILL is very insecure even though we havent been together in 3 years. A couple of years ago I decided that I did not want absolutely nothing to do with him. I did not want to have any type of communication or money from him. I just wanted him to disappear! Because of him I have been single ever since (3 years and counting). I thoroughly learned my lesson!!!!

    • Chelsea

      What made you realize it was time to get out. and how does that affect your sons relationship with his father if you don’t mind me asking. I am currently in the same situation we have been together for about 5 years now. And it has been an emotional roller coaster.

      • Erika

        I realized that it was time to move on when I was constantly stressed out and unhappy. No woman should ever sacrifice her well being for a man thats not even worth her time. No man should ever make you feel unworthy. There is a such thing called emotional abuse. When you waste your time with people like this, you miss out on opportunities of finding a REAL man and also you miss out on your own happiness. My son’s relationship with him is almost non-existent (he sees him around 2 to 3 times a year). I felt like he was a bad influence on him anyway. Breaking up with him may hurt in the beginning, but as time goes on your confidence will soar. Afterwhile you’ll be like WTH was I thinking? LOL

  • Adrina

    It is the worst relationship you could ever be in. After mine ended, I stayed single for a long time because it literally drained me. And not to mention, I was going through a death in the family, bad career, and he didn’t give a damn. He was the worst and knew he was insecure. He figured because he didn’t cheat, he was automatically a good man. I’m glad it’s over. And he was hard to get rid of. ugh

    • Sevn

      Wow, so many similarities! I started to think I was crazy or mean for telling myself it was the worst relationship I’ve been in but seeing the posts, the majority felt the same way. That’s good you took some time off and I’m sure the guy who is meant for you will come to you soon.

    • Chelsea

      That’s the same exact way the guy I’m currently with thinks. I honestly thought I was the crazy one in the relationship because he is soo good to me when I have absolutely nothing going for me. He loves the fact that I don’t speak to friends or go out also. This is a huge eye opener.

      • Amira Aminuddin

        omg yessss me too! I thought I was the only one who thought I was crazy! They are so good at making us feel this way! I’ve opened up my eyes wide. He’s a lesson learnt!


    my last “relationship” was with a guy who had mommy AND daddy issues. he told me his mother had passed then he told me his father was dead too…then he said his father was “dead to him”…who lies about death…? dude, take your meds!

  • i’ve learned that insecurity comes in different forms, and manifest itself in different kinds of situations. i dated an insecure man too. he was great all around, but was afraid of commitment because he was hurt before. that lead to strange behavior that confused me and drove me crazy.

  • urightonthis






    • Really?

      I’m getting tired of seeing this comment on every story. Since you got your credit straight, why not pay all of our bills too so you can stop posting! Oh, and I’ll need to borrow the Camaro Tuesday….

      • Kay

        Lmfaoooooooko dead

  • wait…but but wait? is that a white guy in the pic? what the hell? aren’t all things swirl perfect and redemptive?! this is visual BLASPHEMY!!! why are you spreading such LIES?!!

    • Kay

      Pure ignorance

      • RJA

        I wanna thank u!!!!

      • yes. i’ve been working on my formula. glad i’m approaching 100%. takes A LOT of knowledge and hard work to be perfectly ignorant. i do though think i have a bit to learn from you though.

        • Kay

          No I think you’ve learned enough on your own

          • the fact that you have insight to make that observation suggest that you are my superior. i humbly sit at the feet of master kay until she promises to teach me the ways of ignorance.

            • Kay

              I never said I was your
              superior, I just wanted to let you know that statement was ignorant. That is all ,Now Good Day Sir.

              • how dare you call me sir when my rightful title is lord?! your every word is a trespass against me, kay. any how making a statement, or in your case a decree, without any evidence suggests superiority.

                • Kay


  • Sevn

    Omg…I am currently getting out of this relationship, but imagine your 3 months of the situation being 3 years! I finally made up in my mind (not heart) that I cannot go through the vicious cycle, back and forth anymore and I am a shell of a person now. That’s what happens when you give more and more to a person that is insecure, jealous and possessive…they take it and still need more of your attention. You end up being emotionally broke. They’ll look through your cell, facebook (even though i’m not up there, jus saying), stalk, ask you about guys at your job, accuse you of cheating regularly, etc. just to find something to make them feel better. It’s gonna take alot and I’m going to go to support group counseling to talk to women who have gone through what I’ve been through. I had someone who is like a second mom tell me this…You can get everything back except your life.

    • Adrina

      MIne was 3 years too! It’s been 4 years since it’s been over…

    • Amira Aminuddin

      oh my lord, I’m so glad I got out of my relationship of 2 years with an insecure guy too! I knew how insecure he was, so instead of making him more insecure by talking to other guys or going out with other guys, i did the exact opposite. I’d tell him he’s not ugly etc and he’d say I lied. He’d get paranoid, he wanted me to ask for his permission etc. It’s sick. I dont know why I stuck around with him. Its gonna be hard on me, since I gave him my all to the point where it drained me, but it hurted me even more that his insecurities let him to cheating (and he denies it!). Nonetheless, I know that whatever made the relationship sunk, it wasn’t me. It was his insecurities that was truly toxicating.

  • Lucky_charm2976

    I am currently out of my insecure relationship but if I tell ya that was the worse 9 months of my life and not to mention I almost lost my life at the hands of the shell of a man. When you are so insecure that you imagine different scenarios, stalk, chase, intimidate and control because of your insecurities that is not healthy you should probably go seek some kind of help. As a woman, its in our nature to love…but when love is taken and abused this way, something in you is lost.

  • genii love

    I LITERALLY just went thru this. only mine lasted almost 7 or 8 months. its horrible! It drains every ounce of your energy having to constantly reassure someone that you aren’t doing anything outside the relationship. it was exhausting. having to always explain the relationships of every person I contacted or recieved a cal/text from. If i wanted any bit of was only because I was seeing another man (according to him) not because i felt like i was being smothered and needed to be alone for a few hours to just….i dunno…BREATHE. I had to literally turn of my phone so i wouldnt get flooded with texts that went from “i love you so much” and quickly turned to “i need you, why are you doing this to me!? I hope whoever you are with is worth it”

  • Piecana

    FYI that doggish man in your previous relationship was probably really insecure too…. His insecurities were just expressed in a different way :/