Josh Sway
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/ In Dating, Don’t Bring Up Insecurities

Bringing up insecurities only highlights them. It's best to ignore.


All of us are insecure about something. For every guy it is different. Sometimes it might be physical, like looks, height, or (lack of) hair. For others it may be mental: a confidence or self esteem issue, or perhaps a feeling that one is somehow mentally inferior (education, humor, etc.). Others still may be insecure about various environmental factors such as their job, apartment, or finances.

When dating, it often behooves one to have as little insecurities as possible. Unfortunately, many men think that a way to deflect attention from an insecurity is to actively bring it up in either a joking matter or actively mentioning that it doesn’t bother them. This works from time to time, but a much more effective way to combat an insecurity is to not bring it up at all.

The Pretending Strategy Rarely Works

As mentioned previously, a super common way to pretend an insecurity doesn’t bother one is to actively bring it up and tell your date it doesn’t matter. For example, if you are insecure about your height you may say something like: "I don’t care about height, it makes no difference to me." This can work sometime (and it may actually be true, but then height wouldn’t be an insecurity), but often times, women will interpret this as a form of "overcompensating" for an insecurity; especially if you bring it up often.

The reality is, the more you talk about something, the more it likely matters to you. The mere fact that you bring up your insecurity already shows that you, at the very least, think about it. If you start telling her how much you don’t care about it over and over, it will become obvious how much you do care. If you are going to use the "pretend" strategy, or if she brings up an insecurity of yours in conversation, answer firmly and briskly and change the subject.

For example, a girl you are out on a date with who is taller than you asks: "Do you feel weird dating a girl who is taller than you?"

Answers a and b are pretty good:

a. "Nope."
b. "Nope, doesn’t matter to me."

Answer c, seems reasonable, but stick with a or b.

c. "Nope. I have dated several girls who were taller than me in the past and it never really bothered me. I don’t care about height, I don’t think it matters."

It’s easy to not bring it up

So if pretending doesn’t work, what are you supposed to do, tell the truth? No, don’t pour your soul out about all your insecurities (unless you have already slept with the girl, then you have much more leeway), just don’t bring it up! Is it really that hard to go through a date (or two, or ten) without bringing up some of your insecurities? It really shouldn’t be unless you are insecure about many things. In that case, you should be working on overcoming some of your insecurities as most likely, many of them don’t make sense to begin with.

Bottom line: are you insecure about something? Work on it, but if you are still insecure about it when meeting a girl, don’t pretend you aren’t insecure, just don’t bring it up at all.





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