Too Cute For My Own Good

I never get asked out. That’s always been an issue for me. How can someone that’s outgoing, smart, funny, and attractive never get asked out? Unfortunately, it’s the story of my adult life.

It goes all the way back to high school. I was popular. I was involved with just about every extracurricular activity that didn’t involve physical activity, math or science. I got around, socially that is. I was cool with every clique. I got good grades, even when I was skipping class I didn’t get in trouble. I was just gossiping with my BFF about college and boys.

During prom season as everyone was talking about their dresses and dates. I revealed that no one asked me to the prom. A lot of the guys were shocked.

“I thought you had a boyfriend they said. I would’ve asked you,” they said, but you didn’t, I said to myself.

In college my girlfriends had the best social lives. I lived vicariously through them. They had the best stories. They were juggling guys. No one was checking for me. I was tired of being alone so I decided to take initiative. I’ll be the aggressor. Imagine what that aggression looked like for 18–23-year-old young men? Right, they wanted to get down and dirty.

The whispers started.

Where was my man?

Why was I single?

And of course, if you have no man you have to be crazy.

One day and out of curiosity I took a little poll at my old job. I asked random male colleagues if they thought I was approachable? I told them that I was single and have been single for years. The consensus didn’t surprise me.

“I thought you had someone.” One guy even said, “You’re not married?”

“Do you see a ring fool?”

Another guy told me that I carry myself so confidently that perhaps men get intimidated. I refused to believe that. Am I supposed to walk around with my head down? I do understand that men hate rejection just like women so I’m very careful with my words when I make the first move. Yup! I decided that if I was interested in a guy, I’m going for it.

The guy that eventually won my heart gave in to my advances. We lasted for several years and we created two amazing boys. Our relationship ended two years ago. When you get out of a long-term relationship, in my opinion you need time to be alone and regroup. Well I did all that healing and regrouping. I was ready to put myself back out here. I was ready to date. I am ready to date.

I downloaded a few dating apps, maybe too many. I don’t know why women say that there is a man shortage there are a lot of men out here that are looking for love. It’s actually overwhelming. After texting and speaking to this dude on Tinder, we had an impromptu meetup.

Our conversation flowed. He had some stuff on his mind, I was an ear. I had stuff on my mind as well, he was an ear. It felt really good, to just talk and listen to someone different without someone licking their lips then giving me a lustful look. He’s “good peoples” as the grammatically challenged would say.

We shared our stories of breakup, betrayal, and how we ended up on the dating app. We were two strangers, still scarred by our past, but ready to move on and then he said, “I’m sure you have a lot of suitors…” that’s when I went into my Debbie Downer story of never being asked out. He shook his head and told me that, I’m too cute for my own good.

Too cute for my own good? WTF?

His sentiments were the same as the other guys. He told me that men are probably intimidated or assume that I’m in a relationship. What am I supposed to do what that kind of feedback? Exactly what I did years ago when I heard the same thing; Live my life, enjoy my life, do the things I love, spend time with the people I love and if I see a man that I’m attracted to, I will let him know. I do it all the time on those dating apps.

Recently I met a guy, outside of the app. I really liked him. I asked for his number, we texted here and there and then he ghosted me. Ouch! Will his rejection stop me from making the first move? Hell no!

Let me be clear about something. I’m not approaching every man out there. I’m not tossing my hair in an attempt to catch his eye, or to get their approval. What I’ve learned through my experience, as far as dating is concerned is that the perceptions men have of me, is usually wrong. You never know a person’s story unless you’re genuinely interested in knowing and simply asking. Even if that person appears to be too cute for their own good.




Mom, Young Adult Author, Former Middle School Teacher. Age Enthusiast. I write about all the things I just mentioned and more .

Love podcasts or audiobooks? Learn on the go with our new app.

Recommended from Medium

The Technology Apocalypse

The Top Three Marriage-Killing Money Mistakes


My memory gift

DISPATCH FROM TAMERA 1.0 — The Grief of Returning

Sometimes, It’s Better To Be Alone

5 Steps to Getting Over a Breakup in As Much Time As It Takes, Which is Usually a While

The Heart Beats Its Own Tunes

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Starlet Reid

Starlet Reid

Mom, Young Adult Author, Former Middle School Teacher. Age Enthusiast. I write about all the things I just mentioned and more .

More from Medium

How the Ukraine Crisis Teaches Us the Key To Mental Health Wellbeing

To Forge a Strong Sisterhood, Women Need to Hold Themselves Accountable

The Highs and Horrors of LA Dating #1: 6 Months & Text Dumped

How to Break Up With Your Religion — Morgan Motsinger