6 Things I’ve Learned From 6 Failed Relationships

My dating experience started with a boy named Lucas*, a Mormon and decent wrestler from my high school. I was 14 and he was 15, and was the first person I knew who had an iPhone. From the start, the relationship was doomed. His staunch religious parents thought I was a harlot in my tanks tops and denim cutoffs, and did everything in their power to make my life a living hell. They chaperoned dances, put a tracker on his car, and even went as far as to start volunteering at the school several days per week. It was during this relationship that I learned the story of Romeo and Juliet was not as unique and romantic as it had seemed. Being in a “you and me against the world” type of relationship is not passionate, but instead incredibly draining.

Lesson number one: To make a relationship work, you have to get his loved ones on your side. Form a relationship with his mother. Bring her a candle or cookies when she invites you to a family function. Get your nails done with his sister. Have inside jokes with his best friend. Even now as an adult, this is an important concept. Our families hold much more power than we choose to recognize.

My longest relationship was next. Derek was a diamond in the rough, a ruggedly handsome gun enthusiast with the strongest jaw line I had ever seen and a “wet your pants” sense of humor. I met him when I was 15, a junior in high school, and he was almost 17. As the children of two sets of high school sweethearts, everyone assumed we were soul mates, following in our parents’ footsteps. We thought that too, staying together for two years after he moved away with the military and quietly planning a summer wedding. I could have married him. We wouldn’t have divorced and would have had a good marriage. But I don’t want a marriage that is “good.”

Cue lesson number two: Never, ever, ever settle when it comes to love. Derek was really special and I still think he will be an amazing husband and father, but our relationship was bland, boring, and predictable, and I craved something vibrant and exhilarating and exciting. We were the color eggshell; I needed magenta or blood orange.

That’s where Eric came in. He was a bit older than I was and didn’t grow up on the cushy suburban streets I was so accustomed to. He was a college athlete and bought me beer with his real ID. He taught me the mechanics of a record-breaking keg stand. To this day, Eric is the meanest person I have ever known. We had that “fight hard, love hard” type of relationship, screaming at each other one minute, and making out in a coat closet the next. His touch lit me on fire and I pined after him in an animalistic kind of way that was entirely new to me. Eric taught me all about college dating. He came home with hickeys I didn’t remember giving and sweat-smudged phone numbers written on the insides of his wrists. He instructed me in the art of manipulation. He taught me to be icy and carefree and sometimes a little slutty. He also showed me what it feels like to be an option rather than a priority.

Lesson number three: Wait for someone who picks you every time. Don’t date the boys who get all the girls and make you feel lucky you were chosen, the ones who keep you around by reminding you that they “always comes home to you.” Don’t be thankful he drunk dialed you for a ride instead of going home with a seven and a half who bought him two Long Island Iced Teas. Picking you five nights a week isn’t enough. He should pick you every second of every minute of every day.

After Eric and I split, I dated a drug-dealing bad boy named Brad. Brad had a chest tattoo and grew up in the roughest part of the city. He never wore a seatbelt and took me to parties in neighborhoods I had been taught to steer clear of. He had a burner phone. Once, Brad called me at 4 am to pick him up from an apartment complex. When I asked why, he told me he “needed a get away car and alibi.” I made him sleep on the couch that night, and told him to never come back the next morning. He left his watch on my bookcase. For weeks I was afraid he was going to break into my apartment to get it, and regretted letting him know where I lived.

Lesson number four: Don’t date a drug dealer. It is not cool and risky and dangerous and sexy. It just makes you look over your shoulder more and move your emergency stash of twenties to a new hiding place.

Next was Steven. Steven was an honors student I drunkenly met at a Jimmy John’s at 3am. He was smarter than me, raised in Wisconsin, and looked identical to James Van Der Beek. The master of cancellations and excuses, Steven canceled on rain checks time and time again. One day when he asked to reschedule a dinner we had already postponed twice, I informed him I did not wish to see him at a later date. In fact, I did not wish to see him at all.

Lesson number five: Stand up for yourself. Be your own hero and give yourself permission to leave situations that don’t make you feel good. If someone doesn’t value your time, tell them to kick rocks, and go find a person who does.

After Steven came Mitchell, a tattooed casanova who came into my life as a set up by a mutual friend. Mitch came from nothing and had made something of himself, a quality I found irresistibly attractive. In his earlier years he had been a star wrestler at a Canadian university and now made over $100,000 dollars a year climbing cellphone towers and dangling from helicopters making electrical repairs. He was a high roller at only 22, treating me to weekends in Las Vegas, buying round after round of drinks at swanky bars and gambling hundreds of dollars at a time without batting an eye. Though he had some rough edges Mitch looked great on paper, and my mother swooned over “what a gentleman” he was. But behind the scenes, a different story was being told. When I first met him, I was enchanted by his crooked smile and daredevil demeanor, choosing to overlook what I thought was a bit of recreational drug use and telling myself that he just liked to party after a 60-hour work week on the towers. However, as time went on, his pill popping and habit of “less-than-sober” driving became harder and harder to make excuses for. About two months into our relationship, Mitch called me and begged me to come stay the night. I arrived only to find he had taken five Ecstasy pills and washed them down with shots of Southern Comfort and bottles of Corona. He was laying face down on the stairs, half dressed and even less coherent. I stayed to make sure his heart didn’t give up overnight, waking repeatedly to find him thrashing in his sleep or vomiting in the bathroom down the hall. The next morning I got in my car and drove away for good, vowing not to love a man who loved a drug more than me.

Lesson number six: Do not get yourself involved with an addict. Your idea of “sober” and his will never align. He will always be drawn to his drug like a moth to a lightbulb, and even though you know addiction is stronger than promises of sobriety, it will break your heart each and every time he relapses. As romantic as it is to be a lighthouse in the sea of darkness that is his life, he will sink his own ship before you can ever lead him to safe harbor. Do not be a passenger on his boat of destruction.