I Dated Like An Ugly Person For 20 Years

My journey to self-worth and successful dating.

I dated like an ugly person for 20 years.

Ugly, of course, is completely subjective. Everyone is beautiful to someone, and everyone is beautiful in their own way. I mean no offense or harm.

What I mean when I say that “I dated like an ugly person,” is that I dated with low standards and low self-worth.

I thought I was ugly, so I got ugly results.

The painful truth is that I didn’t even realize I was dating like an ugly person until after my divorce. This is the story of how I realized my self-inflicted agony and how I finally stopped.

And how, as soon as I stopped, my life completely transformed.

How Ugly People Date

During the 20 years before I got married, I dated like an ugly person. According to my mom, I got sent home from kindergarten for kissing a girl on the cheek during recess.

So scandalous.

My mom and the teachers explicitly explained the inappropriateness of playground cheek kissing. I’m a big boy. I can handle the truth.

So, the next day I got sent home for kissing a girl on the arm.

Technically, I followed the rules. I don’t know what they wanted from me. For the next 20 years, I would have just as much trouble in my dating life. In retrospect, the lessons seem very clear.

Ugly people date unexpectedly

As a former ugly person, it always shocked me when anyone showed even an inkling of attraction or interest in me. I just didn’t get it. All I saw in the mirror was ugliness.

Even though I was a skinny 130 lbs, I focused on my pudgy stomach and bony ribs. I grimaced at my non-muscular chest and arms. Instead of a masculine V-shape, my body looked more like a lowercase “b”.

At least in my head.

“Wanting to be someone else is a waste of the person you are.” — Marilyn Monroe

It always flummoxed me when anyone else flirted with me. What I didn’t realize then is that they could tell my surprise.

Many of them interpreted my shock to mean that there must be something wrong with me that they didn’t know. Therefore, they subconsciously agreed with my own evaluation of myself.

I didn’t think they should like me, so eventually, they didn’t. But it wasn’t because I was ugly — it was because I thought I was ugly.

Ugly people date with scarcity

I also viewed dating as if there were only a limited number of people attracted to me. If I screwed up with them, I would die sad and alone.

This approach ruined many of my relationships before they got off the ground. I overly pursued, came on too strong, expressed too many feelings too soon, and refused to be myself in case it ran them off.

I didn’t want to make my girlfriends upset because I believed I only had a limited number in my lifetime.

If I screwed up too many times, I’m back to the lonely death.

As you can imagine, this is a terrible way to date. It reeks of desperation, squashes your authenticity, and parades a trainload of red flags.

Ugly people date other ugly people

Again, I’m not talking solely about appearance here. Besides, no one is truly ugly. There’s almost always someone out there that thinks every person is beautiful.

I’m talking about subjective ugliness that incorporates the whole person.

Still, no matter the definition, ugly people do tend to date other ugly people.

For me, this resulted in lowering my standards for external and internal beauty. It penned me into relationships with other people with low self-esteem and emotional issues.

If you’re thinking that’s not the recipe for true love, you’re absolutely right.

That’s why most of my dating exploits sound like reality TV. Highlights include angry screaming matches at Cracker Barrel, drunken breakups, and enough emotional chaos to fill a couple of episodes of Jerry Springer.

How I Stopped Dating Like an Ugly Person

After my divorce, I took stock of my life. I started reflecting on my poor track record with relationships. I studied the research, read books, and sought feedback from people who seemed to be killing it in the dating department.

It became clear very quickly that I was dating like an ugly person.

I needed to make a sweeping change. I needed to drop the “ugly person” label and replace it with something fresh. Something that might undo the wreckage of my childhood, retrain my brain and refocus my life.

I treated myself like a beautiful person

I didn’t value myself, so what made me think anyone else would value me any higher?

I was projecting my own low self-esteem on other people. They had no choice but to accept my own evaluation of myself. Besides, who knew me better than me?

“Beauty begins the moment you decide to be yourself.” — Coco Chanel

So I started working on how I viewed myself. I began to consciously focus on my good qualities.

I had a full-time job, I was a good dad, I had a car and a house. I began to remember all the compliments other people had given me over my entire life.

You’re a good man

You have your stuff together

How are you still single?

You’re pretty cute for a white guy

That last one I got from a random girl in high school in between classes. I think she may have had a locker near me.

Whatever the case, her off-hand comment stuck with me.

I spent time every day thinking about all the positive things people have said to me over the course of my life. I finally let all of the compliments in—instead of ignoring or dismissing them.

I used them as daily affirmations to boost my self-esteem and self-confidence.

And it worked. Over time, I began to see myself as highly valuable. I started to see myself as a beautiful person.

I behaved like a beautiful person

Because I valued myself, I started changing my daily habits. I worked out more. I ate better and healthier foods.

I started going out more with friends. I even started experimenting with new activities like kayaking, sand volleyball, and rock climbing. I focused on my mission of becoming a full-time freelance writer.

A crazy thing happened.

As soon as I started behaving like a beautiful person, other people started treating me like one. I noticed more attention and attraction from others everywhere I went. I got more looks and more smiles.

This only served to reinforce my belief that I was a beautiful person.

I decided I deserved to date beautiful people

For most of my life, I lowered my standards to whoever would have me. That is a sad state of affairs.

This time, I didn’t put any ceiling on the type of person that would find me attractive. I realized that attraction is intensely subjective.

Again, as soon as I made this mental shift, it seemed to have an impact on my dating life. When I raised my personal standards and focused on my personal preferences, I started attracting other beautiful people.

“If you don’t love yourself, nobody will. Not only that, you won’t be good at loving anyone else. Loving starts with the self.” — Wayne Dyer

How I Dated Like a Beautiful Person

I also noticed that I started dating differently.

I stopped spending hours endlessly scrolling through dating apps. When I matched with someone, I didn’t spend weeks or months “getting to know someone" over messages.

Instead, I sent a few texts back and forth and then set a date.

This saved me tons of time and resulted in more in-person dates. I usually didn’t text or call much before the dates because I was busy with my mission, hobbies, and friends.

That made the dates more exciting because I had so much to learn about the other person.

I also started making friendly eye contact with other people that I came into contact with on a daily basis. I smiled and chatted with strangers. I became playful with everyone around me.

I started treating everyone in the same confident, fun, and positive way.

What blew my mind is how quickly my schedule filled. I had to shut down the dating apps several times because I was just too busy. I began setting dates a few weeks in advance.

Each small behavioral change further reinforced my self-worth.

Eventually, I didn’t rely on other people to feel good about myself anymore. Some women were interested in me and some weren’t. And that was perfectly okay. I knew my own value and I also knew there were other people out there that highly valued me, too.

I just had to find them.

Takeaways

I dated like an ugly person for a long time. My hope is that, if you recognize yourself in any of my past dating stories, that you might use this article as an impetus to provoke change.

Dating like an ugly person simply means that you do not value yourself. Therefore, others don’t either.

Dating like an ugly person is a terribly hard way to date.

You can change your self-evaluation if you want to, but it might not be easy. You start the moment you recognize that you are limiting yourself and your worth.

Here are the takeaways:

• Immerse yourself in the memories of all the compliments you’ve received over the course of your life.
• Spend 5 to 10 minutes per day soaking in the positive feedback from others.
• Repeat affirmations to yourself about your worth.
• Get busy with friends, fun activities, and your personal life mission.
• Remind yourself that beauty is subjective. There are people out there that find you absolutely stunning.
• Don’t settle for anything less than someone who thinks you’re amazing. Not perfect, but perfect for them.
• Don’t spend all your time texting, calling, or scrolling through dating apps.
• If you ever experience moments of self-doubt, pause to remind yourself that you are a beautiful person that deserves love and respect from other beautiful people.

Parting Thoughts

Beauty is, indeed, in the eye of the beholder. But when you trap yourself with your own self-limiting thoughts, you construct an ugly prison around you.

I like the saying, “Whatever you focus on magnifies in your life.”

Many people have said something similar, so I don’t know who said it first. What I do know is that I find this statement to be true in all areas of life, including relationships.

Yes, there are traditional beauty standards based on biological and cultural programming. However, that’s not where the story ends.

No one is truly ugly. It’s all subjective. Perhaps the ugliest person is the one who is ugly to themselves.

It’s past time we embrace our beauty.

“To love yourself right now, just as you are, is to give yourself heaven. Don’t wait until you die. If you wait, you die now. If you love, you live now.” — Alan Cohen