Dating with Low Self-Esteem: Here's How to Do It

January 9, 2019 Sam Woolfe

Low self-esteem can stop you from dating. But when you avoid dating, this can further lower your self-esteem. Here's how to break that vicious cycle.

For a long time, I avoided dating because of low self-esteem and because I always found it too awkward. I limited myself to meeting people spontaneously or in other contexts. But the truth is if you avoid dating completely, you’re likely to stay single for a while. While dating can bring up nervousness and anxiety like a job interview, it’s often something you have to do in order to increase your chances of meeting the right person for you.

But fear of awkwardness hasn’t been the only thing that’s stopped me from dating. My low self-esteem has been an obstacle as well. I have struggled to feel confident in myself enough to make a date happen.

“I’m Too This or That”

I have often avoided dating because of the belief that I have qualities that are either "too much" or lack certain attractive qualities. For example, I have long thought that I am too quiet, sensitive, and awkward. These self-criticisms create a vicious cycle. The more I buy into them, the less confidence I have, and this lack of confidence provides me with a further reason about why I’m not good enough for someone else. Who’s going to be attracted to an unconfident man?

Learning self-acceptance is a long, difficult, and gradual process. There will always be people who don’t connect with your personal attributes. But you can never find the people who do if you reject yourself and reject opportunities to show yourself to others.

Fundamentally, believing you that are "too this or that" comes down to a general feeling of unworthiness. You may think you aren’t boyfriend or girlfriend material (whatever that means). Some people with low self-esteem may try and validate themselves through dating, sexual encounters, or relationships. But healthy relationships tend to come about when each person already feels good enough as they are, or they at least are making a conscious effort to feel that way.

How to Date When You Have Low Self-Esteem

Dating can feel like an extra struggle when you have low self-esteem. But if you constantly avoid it (as I have done), then you will always feel like you’re missing out on a vital aspect of a fulfilling life. Here is one key tip for dating when you are grappling with self-doubt.

Feel the fear and date anyway. When you doubt yourself, you may hold back on a date or act more awkward than usual. That’s fine. Dates get easier over time. It’s important to accept that dating after a long break may be uncomfortable. However, it’s always better to have a bad date and come out glad it’s over than to avoid it altogether for fear of it not working out. The more often you throw yourself into the dating scene, the less you will be troubled by self-limiting beliefs. Dating is a practical way of challenging the negative beliefs you have about yourself. It can allow you to see that you can be completely yourself – expressing all your attributes and eccentricities – and still be good enough for someone else.

APA Reference
Woolfe, S. (2019, January 9). Dating with Low Self-Esteem: Here's How to Do It, HealthyPlace. Retrieved on 2024, July 20 from

Author: Sam Woolfe

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