How to Date When You Have Low Self-Esteem

Dating is hard. Period.

It’s even harder when you struggle with low self-esteem.

How do you put yourself out there when you don’t really like yourself?

For years, I hated the person I saw in the mirror. I grew up as a bit of an “ugly duckling,” and when I did develop into a somewhat conventionally attractive person, I still never felt beautiful. It always felt like there was someone prettier than me, thinner than me, more charming than me.

I was also unhappy in my job and didn’t feel like I was particularly good at anything.

I was on a swim team, but never won any competitions.

I liked to paint, but my art was just not very good.

I exercised a lot, but I didn’t have abs or a tight, toned body.

The only thing I ever seemed to be good at was drinking.

Who would possibly want to date me? Well, reading that, I probably wouldn’t want to date me either.

We all know the age-old advice of love yourself first, and I do agree that we have to spend time getting to know ourselves to be in a relationship, but I also don’t think that we have to hit the pause button on dating just because we’re not “there” yet.

I decided to use dating to better understand, like, and befriend myself.

It didn’t happen instantly, but here are a few ways I practiced self-love while dating:

I became curious about my date.

Instead of putting them on a pedestal, I asked questions about how they got to where they were in their life; I asked what it was they liked about their work, what motivated them. And then I thought about these questions for myself. What did I admire in my dates that I felt was missing from my own life? How could I embody that?

I practiced positive self-talk.

I learned to become my own hype-woman, standing in front of that mirror, and telling myself not that I was beautiful, but that I was capable, and brave, and had the strength to do the scary thing.

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I knew that saying clichés like “you’re beautiful” weren’t actually helpful but telling myself that I had the skills to overcome these feelings was empowering. (Therapy helps, too.)

I stopped dressing for the male gaze.

I used to feel that to be attractive, I had to wear tight clothes, look sexy (but not too revealing), and show off my “assets.” When I stopped dressing for how I thought other people—men—wanted me to, and I started dressing in what I was most comfortable, my confidence sky-rocketed. I was no longer self-conscious on dates and no longer believed that I had to be attractive to “hook” a partner.

I learned to ask myself if I actually liked the other person.

A big part of having low self-esteem has to do with taking rejection personally. If someone doesn’t want to pursue us, we interpret that as I’m not x enough. Instead, we can rephrase rejection as a gift. We often get so caught up in seeking validation, we forget to ask if we actually wanted to be with them in the first place.

This person wasn’t right for me. Now I have the freedom to find someone who is!

I stopped focusing on outcomes and learned to appreciate the process instead.

I used to feel embarrassed talking about my art or my hobbies because I didn’t feel like I had anything to show for them. I’d tell my date I painted, but I’d follow that up with “but I’m not very good,” immediately self-deprecating before they could.

When I started to enjoy art for art’s sake, when I remembered that I loved to swim or exercise because it makes me feel stronger and healthy, the way I talked about these interests shifted too.

My dates could sense my excitement, and no one ever asked how successful I was in these areas—they just admired that I had interests I was passionate about.

I also learned to enjoy the process of dating. By rephrasing rejection, dressing in ways I felt comfortable, being curious about the other person, and changing the way I spoke to myself, I found the joy in dating again.

Confidence is sexy. Curiosity is sexy. And admitting our vulnerabilities is sexy too.

We don’t have to be the best at anything to be worthy of love.

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This post was previously published on medium.com.

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