What I Learned About Dating From My 17 Year Old Self

What I Learned About Dating From My 17 Year Old Self
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I am the type that loves love and relationships. I hate the dating part though. It’s this awkward space full of getting to know someone and that does not always happen easily. I like things that happen organically and naturally. So now at 37, I find it both irritating and aggravating to have to navigate the waters of dating.

The dating world is full of Netflix & Chill and role reversals. It’s actually quite confusing.

The truth is, I’ve never been good at dating. Men nowadays want to do the least and get the most it seem. I’m a connection and conversation type of girl. And when it came to my standards and building standards about how I want to date now, I started thinking about all of the things that I learned about dating over the years.

I had this boyfriend in high school. He was a bit rough around the edges to say the least, but he was one of the sweetest people I knew (he would not want me to openly admit that to people). We were the total embodiment of opposites attract, but got along so well.

He always took me on dates- he paid every time. So this one time, I thought ‘I’m going to pay’, because I was a renaissance woman and had my own money right?


We pull up to the theater and I practically jump out the car to go get the tickets. He would always hand me the money to go and pay for the tickets while he parked and this time I did not want to take the money. The car had barely come to a stop before I jumped out. I run up, pay for the tickets, feeling good about myself. He meets me at the ticket window, I flash the tickets, and he grabs my hand and we walk in and enjoy the movie.

He still hadn’t said anything about me paying. I thought I had been triumphant.


We get in the car and decide to go to the city to go to a restaurant to eat. He pulls off and before we can leave the parking lot, he comes to an abrupt stop.

“Don’t ever do that again.”

I tried to pretend like I didn’t know what he was talking about, but he wasn’t having it. He went on to explain that me paying for the tickets felt disrespectful to him and all that he was taught.

“I know that your mom is this really strong person, and that you can do a lot by yourself, but as long as you are with me, you never pay for anything. That’s the way that I was taught by my dad and I like to do that for you. So put that women’s independence stuff aside.”

He basically summed it up and told me that I should never pull out any money as long as I was with him and to think to do so was disrespectful.

His final words on the subject, “Never date a man that expects you to pay for anything. You’re worth more than that.”

He gave me back the money and we never spoke of the subject again.

That stuck with me. Now, I’m #girlpower on just about everything in life. But I feel like while there are things that I expect from a man and dating that I am not willing to compromise.

My 17 year old self went on dates, enjoyed people’s company and was a bit of a socialite. My 17 year old self required that a man take me out on dates and that we spend time together doing things, not sitting around chilling. My 17 year old self would not be alright with a lackluster connection with someone and would not hesitate to drop the man who did not approach her with intelligent conversation and ideas on what to do on the dates he would take me on. My 17 year old self appreciated being a young woman and learned quickly that it was okay for the man to be a man, and that when he was, it did not make me any less of a woman. My 17 year old self was okay being alone versus dealing with someone who did not meet her needs because she had more than enough on her plate to do anyway. My 17 year old self knew that she had options and would not chase after someone who was not respectful or compassionate.

So my 37 year old self should not be struggling with dating as a concept. I’ve been here before. It’s not foreign territory. My 17 year old self has already paved the way, my 37 year old just simply has to listen.

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