9 Lessons I Learned From Dating the Devil

Valentine’s Day is upon us and the only thing I’m looking forward to is a text from my Mother and a snap from Team Snapchat. The simple joys of being single 

In light of National Love Day, I decided to write an article on what I learned from being in a toxic relationship. But don’t worry, it has a happy ending…

“I hope you enjoy being miserable,” my soon to be Ex-girlfriend mumbled as she walked down the spiral staircase of ‘our’ remote, isolated loft and inevitably out of my life. That loft resembled striking similarities to the direction I was headed – lonely and isolated, being drawn down a spiraling pathway into an unknown darkness.

There was no use arguing with her, we had done enough of that already. She was right, I was miserable. Between sleepless nights on the couch, a mountain of debt, no real plan for the future, and a severe drinking problem (among other things) – you could say miserable was an understatement.

Miserable, by definition, is: “wretchedly unhappy or uncomfortable; pitiably small or inadequate.” The problem with being miserable is the belief that there is no other alternative. You will forever be incapable of achieving success and happiness. This view forces the miserable to act on impulse, seeking quick fixes to end the sadness. Little do we know, these fleeing acts are pushing us further and further down that spiral pathway to darkness.

While I do admit that I wasn’t a very pleasant human to be around in those days, she was no peach. She completely broke me down. I hadn’t started making the money she’d hoped I would yet, so she used that to destroy my ambition. Instead of encouraging me to grow, she continually reminded me of my flaws and the dreams I hadn’t accomplished yet.

I did absolutely everything I could to hold us together. I tried meeting her demands of cutting out friends, not drinking as much, taking vacations, and spending money I didn’t have on a new condo for us. She fully consumed me and had control over my happiness entirely. To tell you the truth, she probably should’ve been gone a lot sooner than that gloomy summer day in August when she left me in that empty loft.

So, there I was feeling alone again. I stood in that empty house and realized that my entire world just came crashing down. All the pain I had gone through to hold us together resulted in me being the loneliest and most depressed I had ever been.

When we decide to invest all our time into people who care little about us, we no longer recognize what our own happiness looks like. It is important to love and cherish every person who comes in our life, but we can do this without losing ourselves in the process.

Though that relationship was quite toxic and almost broke me entirely, I am forever grateful for it. If it wasn’t for her, I wouldn’t have decided to change my life and become the person I always dreamed of becoming. I give her the credit for inspiring me to become the best version of myself. So, I will take this time to thank her for that.


1. Relying on other people for your own happiness will result in your own misery

For most of my life, I’ve had someone determining my next move for me. Whether it be a parent, teacher, coach, friend, girlfriend, etc., I’ve always depended on someone to push me along. And because of that, they were the first people I blamed when things went south.

That isn’t fair. It isn’t their responsibility to ensure I am happy. It’s mine. We can only be responsible for our own path. We need to let others have theirs.

2. The only thing screaming does is annoy the neighbor

Please stop screaming at each other. Learn how to talk to one another and then maybe something will get resolved. One thing is for certain, your neighbor will appreciate it.

3. Self-medicating to bury the problem will probably result in sleepless nights on the couch

When things got bad in my relationship, I did what any broken-hearted twenty-something would do – I dove straight into a bottle. Whatever I could do to run from the problem, I did. And as a result, I spent countless nights on the couch watching The Office hoping Steve Carell would change my mood.

4. Buying the solutions to relationship issues will most likely create more, expensive issues

Spending money you don’t have on a person who really doesn’t care about you will create more problems. You can’t just buy things and hope they patch up the relationship. You need to learn how to talk things out and communicate…then go take a cruise to the Bahamas 

5. Jealousy is toxic

I must’ve been peanut butter because she was Jelly… all the time (I know, another lame Dad joke). But in all seriousness, jealousy is not the answer.

You need to learn how to trust one another if you stand any chance at a healthy relationship. This is where establishing trust and boundaries early on is vital to growth in your relationship. Be open with your partner and tell them what bothers you early on so they have an idea of what not to do. It’ll make the conversation a lot easier down the road if the situation presents itself.

6. Blaming someone else for your problems will result in more problems

When I made the decision to become fully dependent on myself to be the person I wanted to be, I stopped blaming individuals and circumstances for my actions and took responsibility for them. It was then when I began to be at peace with my past. I started making decisions for myself, not on impulse and not influenced by what people wanted me to do.

As my buddy, Rick Warren said it, “At some point in your life, you must decide whether you want to impress people or influence people…” I opted for the latter.

7. Compassion creates passion

Empathy and compassion are the two gifts we give the world, and we become more and more alive each time we share that gift. Learning how to be compassionate and understanding to your partners needs will create a healthy environment.

I believe Stephen R. Covey in, The 7 Habits of Highly Effective People, said it best, “Seek first to understand, then to be understood.”

8. Being vulnerably authentic is the key ingredient to building trust

Ladies, I think you have this one figured out. This is one every dude needs to hear. We don’t always have to be this macho figure who has it all figured out. We need to learn how to be vulnerably authentic and express ourselves in a way that reveals we do love and care.

I think our significant others may appreciate it if we learn how to tell them we love them, and not just when we want something… if you catch my drift.

9. Letting go was the best decision I ever made 

I saved a ton of money on my Valentine’s Day by switching to single  Learning to let go entirely, and not be one foot in and one foot out, was the best decision I ever made. I cut ties completely and finally found myself.

Now I know, with certainty, when the next one comes around I will be the best version of myself…because she deserves it.

Hope this wasn’t too painful of a relationship post for you. Happy Valentine’s Day to all you love birds out there.

And to all you helpless singles…call me, maybe?