Do You Always Repeat the Same Dating Mistakes?


It’s often said that “insanity is doing the same thing over and over again and expecting different results.” So why do we do it? Why do we repeat the same dating mistakes over and over again? Dating the same type of toxic person, enabling bad behavior, tolerating disrespectful treatment, falling for the same excuses, letting ourselves be used … and the list goes on and on. Good news is that you’re not alone. Bad news is that this behavior is keeping you single. I asked my followers on Twitter Did you ever look back at your dating life & wonder “what was I thinking?” and over 80% of respondents said yes and 50% said they repeated the same mistakes. So what do you do?

Do You Always Repeat the Same Dating Mistakes?

If you’re always repeating the same mistakes and you’re tired of being single and frustrated with your dating life and feel that you’re unlucky in love … there’s hope, BUT it will take some reflection and work on your part.

Firstly, ask yourself:

If you said yes to any of these, you might be the author of your own dating misery. I know that it’s a hard pill to swallow but we’ve all been there. Me included. I didn’t realize it but I was choosing the wrong people to date. I was deliberately rejecting people who would have been better for me because they didn’t excite me and they didn’t make me weak in the knees. I deliberately choose the most charismatic guy in the room, the one who’s energy was electric. With that kind of chemistry why would you want anything else? I soon learned the error of my ways. I WAS the author of my own dating misery and was calling it bad luck, it wasn’t bad luck, it was bad choices. Plain. Simple.

How To Stop

Stopping destructive dating behavior is easy when you recognize why you make the choices that you do. That’s the important part. When you know why you do it, you can do something about it. So let’s go back to our original list:

  • if loneliness is clouding your judgement, then engage in more social activities, join a meetup group, take a class, plan outings with family and friends.
  • if you’re emotionally unavailable, try and determine why you are and work towards solving it either with family, friends or a professional.
  • if you’re not being true to yourself and your values, ask yourself why and be confident enough to let go someone who doesn’t qualify, someone else will come along.
  • if you’re not marketing yourself the right way to the right people, then think about what it is that makes you different and stand out from the crowd and always be confident about who you are, in addition to always putting your best foot forward.
  • if you’re clinging to false hope in dating, then you need to give yourself a reality check – is your current situation going nowhere fast? are you living on wishful thinking? are you ignoring red flags?
  • if you choose the one that makes you weak in the knees, most likely you like that “high” of crazy chemistry, but ask yourself if it comes with stability and refocus on what you really want? Remember that a fire that burns fast and hot burns out just as fast.
  • if you’re enabling bad behavior and making excuses for them then ask yourself why you’re doing it and what you’re getting out of it, they are the ones benefiting while you’re most likely miserable.

Some food for thought. If you always repeat the same dating mistakes, then think long and hard why you do it and make a conscious decision to stop. Don’t define yourself by your mistakes but learn from them and move on. It’s an experience, valuable experience. You’ll be much happier for it. Don’t be a glutton for punishment. You deserve to be happy and fulfilled. So CHOOSE happiness.

READERS: Do you repeat the same dating mistakes? Why do you think that is? Share your thoughts & perspective in the comments below!

Your Sister in Dating Bliss,

Single Dating Diva

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  1. I think it’s human behavior to choose the one we are attracted to but I have to admit these fade fast. I admit I have been guilty of this wanting to date the handsome guys that I lusted after versus the good guys. Once i admitted this to myself is when the good guys who would make a good match were gone.

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  2. This is a great article. I like that you suggest asking ourselves questions. I find when I ask myself questions and sometimes more than once. I get an answer back, if i am willing to listen lol. Sometime this process takes time.


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