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I like to think that each person I’ve dated has led me on the path towards my “one true love," which is of course a positive spin on the reality that most of these dummies had no clue how to treat a girlfriend, and possessed the fabulous talent of continuously letting me down.

Starting with my very first camp boyfriend who held my hand and almost kissed me beside the lake but got too scared so he dumped me instead, to the financial analyst who took me to fancy dinners but took longer to blow dry and gel his hair than I did, these men have simultaneously made me lose my mind while teaching me how to possess a balanced, adult loving relationship. Each and every one I hold near and dear to my heart, because they have shown me what I need in my life companion, and what I definitely do not want to deal with for the rest of my life.

Here are some of the lessons I’ve learned along the way:

#1: "Chill" Is The Enemy

Don’t be fooled by their charm and nonchalant attitudes, men who insist they are "chill" and "laid-back" can be tough nuts to crack. I get it, the whole sweet and simple way of life can be enticing—but it’s not realistic. Life is not all flowers and sunshine, and when the going gets tough, these guys often freeze, deer in the headlights style.

It’s no fun to become their mothers, constantly nagging them daily about what they’re doing to figure out their career. You aren’t their mother, you’re their girlfriend. You can’t make them into the strong and motivated man that you want them to be, they have to figure it out themselves. It gets old, really fast. When things get serious, sometimes his “laissez faire” is more stressful than chill. 

#2: Some Mysteries Are Better Left Unsolved

Back in high school, there was nothing better than a tall handsome cool guy; I simply could not get enough! His leather jacket and overall cool persona got my heart a flutter…until I needed him to perform in social situations.

Just add a room full of people, like my family, and suddenly that aloof charm had my heart racing, with anxiety instead of love.

I’ll never forget the time I was dating a Mr. Mysterious and when we were with my entire family, he was off in the corner observing as my family desperately tried to include him. His mysterious persona read to them as bored and unapproachable. I soon discovered that his brooding ways meant I could no longer have fun at any social function. That's the thing about mysterious types—they usually only appeal to you. Everyone else in the room just sees rude. 

#3: White Lies Can Bite

We all tell little white lies when we’re first wooing a man. We “love nature”; baseball games are so sporty and fun; I love cheap beer!; you know the drill. It's harmless—nothing will come of it, right? 

Wrong. So wrong.

I told my ex that I was really into camping, and next thing I knew, we were packing a tent, kitchen supplies, and sleeping bags into my trunk on our way toward Michigan. My sisters snickered, they didn’t think I could last. My white lie was so convincing that I had even begun to believe it was true—I was the perfect little camper! That is until we set up camp in the middle of a swarm of blood-thirsty horse flies. We spent the entire camping trip swatting and jumping into the tent for protection against their bites. 

Moral of the story: pretending for the purpose of impressing never turns out well.

#4: LDRs Only Work If He's Willing To Go The Distance.

I dated a guy who lived in New York, and it was going really well. We had a really great time together, but it wasn’t serious. Just as things heated up, he received a job opportunity in Chicago.

Fast forward to his departure, a tearful goodbye at the subway stop in Brooklyn and the confusion of “what we would be” still lingering in the air. We continued this non-relationship relationship for about a year. One whole year of nights spent on the phone helping him with his loneliness and depression while my friends were out partying, trying to be his support. I kept asking him when he could come see me, and I always got “I don’t know when I can get off work, babe” or “I’ll see what I can do, ok?” The relationship ended, and I was exhausted from my lack luster LDR. 

Lesson learned: if you’re going to go the distance with a man, find that man who will drop everything to come visit you, because you are worth it. If he doesn’t see that then he isn’t the right man for you!

#5: Money Can’t Buy Class

I’ve always shied away from the "finance guy." New York City is filled with them; suits tailored perfectly, cologne permeating the nostrils from 7 feet away, hair coifed entirely too much for comfort…need I say more? After a string of artists and bohemians, I decided I was eliminating an entire breed based upon stereotypes. Certainly not every young finance professional fell under these categories, right?

The man I dated was handsome, smart, successful, funny, and boy did he know how to wear a suit. He took me to all the hip fancy restaurants and always gave the server his card before I could catch him. I had never had anyone spoil me in this way before; I felt like a princess! 

Then I noticed how he would speak to the servers and cab drivers; everything was on his terms. Suddenly, the spell was broken. He had almost charmed me into believing that he was respecting me, so close! That brought me back to the realization that money can’t buy class, and a good man treats everyone he meets with equal respect no matter their profession.

#6: His Mom Matters—A Lot.

The boyfriend’s mom is a tricky beast to tame; you have to be warm and complimentary, while showing that you can stand your own ground. I dated a guy whose mom was a professional powerhouse. She ran her own business while raising two amazing children. I was intimidated. She was always polite to me, but I knew she wasn’t really a fan of my relationship with her son.

I did everything I could to make her like me; I would bring her gifts, talk about how wonderful her home was, clean my dishes, and always say please and thank you, but none of that mattered. She still had disapproval written all over her face. The thought of dealing with her for the rest of my life was a huge downer, so much so that when we eventually broke up I silently celebrated the knowledge that I was finally free from his mother’s clutches. No matter how great the guy, a lifetime of contending with crazy in-laws is something to seriously take stock of.

#7: Dogs and Men Are Not The Same

As women, we have the natural instinct to “fix” people. Our bodies are designed to nurture. It is in our DNA to rescue a lost wounded dog on the side of the road, take him home, nurse him back to health and adopt him. This female mentality often translates “wounded puppy” into “human male”.

I’ve done it many times; found a man who seems lost and alone and is loaded with all kinds of baggage yet believe that I can take him in and fix all of his problems. We have to remember that men are not dogs. I know it’s hard to hear this, but you are not Snow White and he isn’t one of the adorable furry woodland creatures; go find a Prince Charming who doesn’t need fixing; he just needs a partner in crime by his side!

#8: Labels matter. They Just Do.

"DTR" is definitely one of the best acronyms I have ever heard in my entire life. I have to thank the poignant reality show The Hills for this one. Every relationship begins with the awkward terminology dance. This is driven by everyone else in your life asking, “So, what are you guys? Is it official?” (Thank you society for always implementing labels so that we may feel constantly insecure about our current professional, dating, or life situation!)

Although labels seem silly, they do have a sneakily irritating way of making sense. My ex would always ask me why we had to label what we had. He didn’t see what the difference was between calling me his girlfriend or not. I saw his point, but I also realized that calling someone your girlfriend isn’t just a label. It’s telling the world that you are fully devoted and committed to another person and that you respect them enough to introduce them to your friends and family as your partner. If either party is hesitant to make that declaration, there are deeper issues. 

#9: It's Not Always "OK."

One of my exes was a real go-getter; that was one of the things that attracted me most about him. He was in a rigorous master’s program, working at a firm to make extra money, and running a non-profit in Africa. Sounds like a real dreamboat, right? His drive and intellect made me swoon. During our relationship, I was going through a transitional period in my life, finally out of school for the first time since I started kindergarten, so I was struggling. The real world was exciting, but it was also terrifying. I was grateful to have him, but I soon began to feel that I couldn’t tell him what was really on my mind. Every time I expressed any sort of distress or anxiety, he would shut me down with, “It’s going to be ok!”. 

When my apartment got bedbugs for the second time in four months, he didn’t console me as I was balling my eyes out from stress and disgust. He simply said, “it’s going to be ok.” Guess what, life isn’t always “ok.” Sometimes it truly sucks and things go wrong. I began to recognize that I couldn’t share a giant part of my life with him because he wouldn’t acknowledge it. It didn’t matter how many non-profits in Africa he ran, if he couldn’t be there for me when I really needed him, he wasn’t the right one for me. 

Photo Credit: Nirav Patel