10 Love Lessons Learned by a Man

Jay Hall
7 min readSep 9, 2020
Photo by Scott Broome on Unsplash

We all go through phases in our lives. These phases aren’t who we are, but rather the building blocks we need to discover who we are.

Then there comes this point where the stars align and lightning strikes. Suddenly, we know who we are. It’s not that we know our true selves wholly but we do assemble the essence that is our true character one phase at a time.

Recently, I went through my final phase in discovering who I want to be when it comes to love. It was triggered by an event—which I’ll get to later—and the revelation was unexpected, to say the least.

Confused Kid

My first “real” girlfriend was Marsha. She was far more experienced than I and eventually she called it off because that inexperience was painfully obvious. I then dated several other girls throughout my junior high and high school experience, learning quickly that I was a romantic at heart.

My first foray into romance was with my girlfriend, Leigh. I had her come over to my place for a candlelight dinner at 3:30 in the afternoon. Disaster, right? It gets so much worse. She only had 30-minutes before her bus left to take her home, the candles kept blowing out because of the strong A/C in my parent’s basement and to top it off, I didn’t know how to cook.

As high school continued on I started to realize that I fell hard for every girl I met. Heidi, Melissa, Sarah, Shannon, Lisa, Katherine, Amanda, Cat, Vanessa … the list is long. Each, I fell for, and each either got sick of my timid attitude towards dating or we broke up because I couldn’t maintain any level of excitement as I started the quest to make something of myself.

Becoming a Confused Adult

As my adult years rolled on I dated a lot. Being in the nightlife scene I had my pick of beautiful women. Most of the relationships were surface level but I did have some long-term relationships that ended in a variety of ways.

Nina was a woman I should have never dated. The relationship was passionless unless we were fighting and I honestly had no idea what to do with her.

Kayla and I started out hot and heavy but it fizzled as life got hard and she cheated.

Lindsay and I had a fantastic relationship but I proposed too soon and she buckled under the pressure.

Dez and I started out the same way but it fizzled as life got hard and she cheated.

Krystal left me for her ex twice and strung me along while dating a new guy.

In between, I have several short-term relationships that I treasure. Sarah, Kristen, Sabrina, Michelle, Michala, Pam, Jill, and others were relationships that lasted under three-months and I remain friends with all of them to this day.

The Blame Game

For those relationships that ended poorly, I’ve been harsh in my criticism over the years about the cheaters and liars. Ultimately though, I didn’t look inward because that is a life skill I hadn’t picked up until recently.

It’s actually my hypothesis that many never learn this life skill at all. How do I know this? My mother and father broke up after my mom cheated. She did so after years of neglect and boredom. To this day, my father and sister put the blame solely on my mom for ruining their marriage.

They can’t see that there is a thread of blame for all to pull on whenever a relationship fails.

My Fault

If you were to talk to my exes, I feel confident that they would say my intentions were good but my execution was poor. They would also likely say that I created a level of passion that could not be maintained. They would be right.

I find love is the one place we can look to discover the bright and shining parts of our character but it is also where our most glaring character defects exist, as well.

My most glaring character defect is that I start something with incredible passion but then I let it fizzle. I do this time and time again.

So often, after learning I had been cheated on, I shook my fist at the sky and asked, “Why can’t I just find love?”

Turns out, I didn’t deserve it and the event I spoke of earlier is what helped me realize this.

Hurricane Dani

I once dated this gorgeous model type with a wicked sense of humour named Dani. Her smile could light up a room and her legs would make any man swoon.

We went on a couple of dates but my emotional maturity was somewhere between a rock and a mosquito. Not realizing what I had, and in the face of other challenges, I treated her unfairly. I wouldn’t say poorly, but definitely not as she deserved.

She went on to live her life as I did mine. Every so often though, I’d check in and get rocked by her beauty. A few times, we’d speak through Insta DM’s but never much more than trading a couple of jokes.

Eventually, she got engaged and it was when that happened that I knew I had unresolved feelings for her. Examining those feelings is what led to my revelation that I didn’t deserve love.

I believe that she has since ended her engagement and I’ve tried a few times to reach out with little response. Now, maybe it’s too early but it’s more likely that she remembers the idiot I was in the past.


Reflecting on how stupid I was is what made me really examine how I’ve been towards my girlfriends, my exes, and the general topic of love.

I’ve been a child and unless I admit that and atone for my mistakes then I will never find someone I can maybe fall in love with for the last time. Guys, if you think I’m being a bitch then you’re probably just not at the point where you can understand this yet, and you may never get there. So many of us settle for the person that shows us attention and slap the label of love on it.

I don’t settle! I never have … not in work or play.

So, as I continue on this journey called life I do so with my eyes wide open and my better self in tact after a lifetime of being a bit of a fool.

I will no longer talk shit about my exes—even the ones that cheated because I led us down that road too. Is cheating justified? No. There are much better ways to handle an expression of happiness. However, I can’t really blame them for looking elsewhere.

I will no longer jump in with both feet and create unrealistic measures of success in relationships. It’s okay to take my time and enjoy the little things. Not everything in a life with someone has to be an event.

I will be myself, and not who I think the woman wants. This is a doozy and an impossible standard to keep. Too often, I’ve tried to be the man for her when I should just be me and find the woman that appreciates that.

Lessons Learned

I probably won’t get to prove to Dani that I am a better man. I will also probably not get the chance to speak to many of my exes and apologize for my role in the disaster that was our relationships.

But, what I can do is be a better man going forward.

The 10 lessons I want to carry forward in my next relationship are:

  1. Texting is for information, not communication. So, “I’ll be home at 7,” rather than, “Here’s the problem I have with you …”
  2. Respect, loyalty, passion, understanding and other relationship principles are a two-way street. I can’t expect any of these from a woman if I don’t give them back.
  3. I won’t dwell on hindsight, but instead focus on foresight. If there was a problem I won’t reflect, but simply correct.
  4. Power phrases like, “I’m sorry”, “I understand”, “I agree” will end the debate or argument. Continuing results in no positives.
  5. If someone brings a concern to the table, I will never minimize it but I won’t be a push over either. Without rational discourse and problem solving no type of relationship can survive. Open communication is required.
  6. Therapists have their jobs for a reason, and one very important reason is that relationships are hard work. We get too close to each other and sometimes that destroys even the most rational debate. Talking to someone about your problems—but more importantly LISTENING to the unbiased 3rd party is not weakness, but rather intelligent.
  7. Recognizing comfort and passion will save myself and the woman I am with years or heartache. I can’t be afraid to say, “This isn’t for me.”
  8. Equality in a relationship is as easy as holding a door for someone. If that can’t be achieved then the relationship will not succeed.
  9. Work will never stand in the way of happiness again, but I also need to find a woman that respects my goals and is on my team as much as I am on hers.
  10. Only fools rush in. No more grand romantic gestures and turning all of life’s moments into events. It’s okay to be calm and present together.

I think many of us testosterone fuelled danglers should look inward more. We’re taught that we can’t be open with our emotions and I was taught that decades ago. The lesson stuck with me until recently. Maybe that’s why I was such a train wreck in relationships. Who knows?

All I know today is that I can still be strong while looking my weaknesses in the eye. Perhaps that is what strength is all about and I can’t wait to share what I’ve learned with the next woman whom I see from across the room and instantly connect smiles with.



Jay Hall

I find therapy in words. 3 types of articles I write: Life Lessons, What If (fiction meets reality) and Nonsense Listicles.