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I’ve said it many times: dating will make you hyper-aware of all your insecurities. Whatever thing is “wrong” with you or you dislike about yourself, there’s nothing like going out with a stranger you find attractive to remind you of it.

We all have an Achilles Heel in dating, something that holds us back. For many, there’s some area of our dating skill set that needs work – for example, like I talked about last time, some need to work on their social skills and the impressions they make on others. Others need to have more realistic expectations. But then there’s the kind of Achilles Heel that’s more personal and less skill-based; I’m talking that one thing you’re insecure about, the thing you hate about yourself and thus assume the other sex will hate it too.

Here’s an example: I have a friend (female). She met a guy, and they went on a few dates. Things went SO WELL that she was genuinely surprised that after 3 dates, he disappeared. Just stopped calling. At this time in her life, my friend had put on weight. Forty pounds, to be exact. This was a difficult period in her life, and the 40 pounds reflected that. She hated her weight. She felt pretty sure that this guy, despite liking her, disliked her weight. He was a good-looking, great guy – why would he date her when he could get a thin woman?

A few weeks went by and she got a call from him. He apologized for disappearing. He told her he had a great time with her and really liked her, but had unexpectedly reconnected with a former girlfriend, and they’d gotten back together. Then, a few more weeks later, my friend was at a farmer’s market and spotted this guy and his girlfriend from afar. And guess what? The girlfriend had the same build she did.

She’d convinced herself he’d rejected her for her weight. Clearly, that was not the case. She did what many people do – date, get rejected, and them blame whatever thing they’re insecure about for it. For her, it was the 40 pounds. For others, it’s something else. I can’t tell you how many times I’ve heard people find some imperfection about themselves and use it as a reason they’ll never succeed at dating. Here are some examples:

  • “Women prefer guys with money and I’m broke.”
  • “Men prefer younger women and I’m over 40.”
  • “I’m short and women always want tall guys.”
  • “People only care about looks.”

To this list you can add balding, shy, uneducated, overeducated, skinny legs, fat legs, small boobs, weak chin, acne, big nose, single parent, divorced… you name it, I’ve heard it.

Sure, dating can be unfair at times. Yet, tons of broke guys have girlfriends. Tons of single women over 40 have active dating lives. I can’t tell you how many short men I’ve known who are quite successful with women. And average-looking people date just as much as the hot ones. What makes these people different? Their “imperfection” isn’t a source of insecurity for them. Or, if it is, they’ve learned to deal with it and find people who like them for who they are.

The problem isn’t that thing you’re insecure about. The problem is your mindset about it. I know it sounds cheesy as hell, but here it is: if you’re comfortable with who you are, others will be too. Grow comfortable with your imperfections and insecurities. Work on them if possible, but learn to accept them. If you do, I guarantee you’ll succeed at dating.


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