The Midlife Bachelor Personal Makeover >> Attitude Adjustment / Mental Makeover Rev 2.0 >> The Dangers of Insecurity …

The Dangers of Insecurity
No mental makeover is complete unless you can find personal security within yourself without the help of others.   What I mean here is that you need to be a secure individual – secure with your midlife bachelorhood, secure with your financial and emotional situation, secure with your looks … basically secure overall.   If you are not secure, then it will show – and you will have a tougher time with dating than you otherwise would.

Every single person is different – and therefore I cannot give you specific advice about how to be secure, or how to avoid being insecure.   [Psychologists and psychiatrists can help you with that, if necessary.]  All I can tell you is that the more secure you are with yourself, the better off you will be in terms of midlife bachelor dating.   Put another way – the more insecure you are, the more difficult time you will have … because women sense insecurity.   [You can wear the “red badge of insecurity” like a big sign on your back or your forehead – without ever realizing that it is there.]  Here are some of these outward signs of insecurity:

Nervous (versus confident) in terms of conversation – if you just cannot have a normal conversation with a woman because she is too hot, then you, my friend, are insecure.   I’m not saying I’m any better – it still happens to me on occasion.   For me, I get nervous if I think a woman is “out of my league” – usually with respect to looks, but possibly with respect to her income.   [In other words, sometimes a wealthy woman intimidates me.]  I get “tongue tied”, and say stupid things.   I usually laugh at myself afterward.

Failure to look a woman in the eyes – this is one that has never happened to me … probably because I am in sales, and am used to looking at people eyeball-to-eyeball.   But if you have trouble looking at a woman square in the face, you are probably insecure.

Constantly or repeatedly asking a woman out – you should never be a pest, but sometimes we slip into this rut for whatever reason.   Anytime you ask a woman out – if she says “yes” but doesn’t subsequently get back to you or return your phone call … you can call her (at most) ONE MORE TIME.   If she fails to get back to you a second time, then she is not interested … and you should promptly move on to greener pastures.  If you keep bugging her, you are insecure – because you do not know when to give up.   In cases like this, just take a break and spend that energy elsewhere.

Calling too often – every woman is different, and every relationship is different.   Generally-speaking, if you are pursuing a new woman to go out with, you should not call her more than once or twice a week UNLESS she calls you or asks you to call her.   It is better to call infrequently versus too often.   You’ll know right away if you should call her more often – as most of the time she will be calling you.   If she never calls you, then something is wrong – you are probably chasing the wrong woman.   The bottom line is – if you are calling and calling and calling a woman, then you are probably insecure.   Give it a rest, and go do something more productive with your time.

Being too nosey – never ask too many questions, and do not ask questions that you really do not want to know the answers to.  Especially when you first start dating a woman, do not ask her pointed questions about who else she is dating, or when was the last time she saw her last boyfriend … because you might not be happy with the answer.   Over time, even if she is still seeing someone else, if you are the man for her – she will devote all of her attention to you.   Just don’t rush it.   Besides – you might scare her off.  If you are too nosey, she will see you as prying and insecure … and she won’t want to talk to you.

Stalking – don’t spy on anyone.  It just isn’t nice, and it might even be criminal.  If you feel you have to spy on a woman, then either she is not worthy of your trust, or you are completely whacked and in need psychiatric assistance.   Stalkers are pathetic as well as insecure – so do not be one!

Assuming too much about the status of the relationship – never assume or presume that just because you have gone out with a woman or slept with her, that she is your new “girlfriend.”   Always discuss potential titles like “girlfriend” with a woman before announcing or introducing her that way.  If you assume too much too quickly, she might be gone before you know it.  Everything is political – and some women are more difficult than others in terms of locking themselves down in a steady relationship.   Play it safe, and don’t assume too much.   Let her stress over what to call whatever it is you two share – after all, she’s the woman (not you).  If you are secure with yourself, then you won’t worry about the status of the relationship

I’ll be honest with you – in general I have personally struggled with many insecurities over the years.   If I was really intent on pursuing a woman, I would make the mistake of over-thinking how I was going to talk to her … and I would wind up appearing really nervous … often turning red.  I am one of those people who have kind of a pink tint to their skin … and I blush extremely easy.   Plus when I know I’m blushing, I get even more nervous … so nervousness tends to snowball for me.  Sometimes I used to actually rehearse what I was going to say to a woman that I was going to ask out – the result was that it sounded almost like I was reading a speech!   Even after I got a date with a woman, I used to obsess over planning the details of the date … where we would go, how the smallest details of the date would progress.  It was crazy because if anything changed spontaneously (like the restaurant was closed, or had a two-hour wait, or something along those lines) then I would stress over it, and the date would not be as fun.    It took me many years to get over what I describe here – the way I did finally conquer it was that after fifteen years of being single, I started to care less about how everything turned out.  In other words, I began to feel that it was great to have a nice evening out with someone/anyone … versus being focused on the mechanics of the date, or what was going to happen between me and the woman.   I had heard all along that as soon as you give up trying – that is when you will meet your soul mate … and I believe it!  You cannot “not try” but you definitely should not “over try”.

As far as “calling too often”, “being too nosey”, or “assuming too much” about the relationship – I’ve struggled with those insecurities, too, over the years … although not nearly as much as some people I know.   The bottom line is that you as a midlife bachelor have to be sensitive to every dating situation – and before you do or say anything, you need to think about the possible implications … because you never want to send a woman the wrong message.   Plus – you are generally better off by not being a pest.

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.