I Suck At Dating: My Top Five Mistakes

Listen, darlings, I have to be honest with you. At this point in life, most people I know are in long-term relationships. Most have been engaged at some point, and even if it didn’t work out, at least they knew, even briefly. Meanwhile, I’m 28, single, and my longest relationship only lasted a little more than a year. I’m not in a position to tell you any secrets to a great relationship.

However, what I DO have experience with is making bad choices in dating—I can tell you a LOT about that. In fact, I even went to the courtesy of making mistakes multiple times until they revealed patterns, so that I could prevent my incompetence in others. So gather ‘round to hear my dating tales of woe, and do as I say, not as I have done.


Dating Mistake #1: Being blinded by beauty.

Once upon a time, I came home from work to find a truly perfect specimen of man hanging out with my roommate. He was 6’4, tan, winning smile, the perfect balance of muscular and slender, and I immediately canceled my plans for the night to be in the same room as him. Within a few weeks I thought this was it. I told my friends I was going to have his babies. Given that I don’t even like babies, my friends expressed surprise and gently tried to bring me back down to earth. But they were not the ones touching his abs; I was off in the stratosphere.

About three months later, I started listening when he talked, and realized this guy had the intelligence of one of your more basic crayons. I remember sitting there, inwardly horrified, as he talked about his plans to study “maybe Chinese” “because it’s like, the future.” After the realization, there was no going back to my ignorant bliss. My friends still tease me about my misguided reproductive desires, though they also still ask to see pictures of him.

So what’s the lesson here? Don’t focus on physical aspects so much that you lose sight of the whole person. Superficial relationships have their place, but you have to keep them at the right level and be able to let go when it’s time.


Dating Mistake #2: Dating a coworker.


I used to work at a large company of young people where office romances were abound. Some of them are married today. However, far more pairings went south and produced awkwardness for involved parties, hilarity and judgment for co-workers, and occasionally, legal trouble for HR. For example, one manager had a babydaddy whose new girlfriend was accidentally put on her team. There were multiple restraining orders. In my case, I dated someone who always talked about having a lot of influence at the company. At first I felt liked by association and then I felt trapped—terrified that if I broke up with him I would be blacklisted.

Office relationships may seem fun at first, but there are so many negative consequences. You have to see this person EVERY DAY—even when you are exasperated to the point that just hearing their voice makes you want to punch their stupid face. The relationship will impact your professional image at your company. You will be gossip. And heaven help you if you date more than one person at the office. Keeping your work life separate from dating makes everything a hell of a lot less complicated.


Dating Mistake #3: Dating someone who doesn’t put it on Facebook.

Their ex re: you. via whatshouldbetchescallme

I know not everyone uses Facebook these days, mostly because it’s a complete relationship-ruiner, but what I’m getting at here is acknowledgement. Maybe it’s that their friends aren’t 100% sure of your name. Maybe they freak out if you leave your toothpaste at their place. The point is, I’ve learned that if they don’t want there to be public knowledge of you, there’s usually a reason, and it’s usually not good. They should be proud to be dating you, and want to shout it to the world. And don’t give me, “I want to keep my profile professional and my life private” when you approved six pictures of you chugging beer and other pictures with random girl friends. Next.


Dating Mistake #4: Getting talked into dating.

So maybe there’s someone who’s really sweet and funny, and you want to give them a chance even though their teeth are kinda weird and they’re maybe not really the kind of person you’re attracted to. I’m all for giving someone a chance, but don’t try too hard to overlook things you don’t like (this is someone you’ll have to see naked, after all). I used to feel obligated with romance and it took me a long time to realize that you don’t owe anyone shit. Don’t lead people on—it’s better for everyone if you are upfront and say it’s not going to work out.

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man holding baby s breath flower in front of woman standing near marble wall

Because nothing says love like a guilt trip. via whatshouldbetchescallme

Similarly, don’t let anyone guilt you out of a breakup. After giving nice-but-unattractive guy a chance, I had a great time being wooed and worshipped but soon realized that—shocker—I still wasn’t attracted to him. I tried to break up with him many times; nothing worked. He guilted me into staying for an embarrassingly long time because he was such a “nice guy,” but I later realized he was manipulative, not nice. When I finally got away, I breathed a HUGE sigh of relief and never looked back.


Dating Mistake #5: Dating someone that you suspect is a bad person.

I once dated someone whose job was basically tricking people into paying a high price for used equipment (turns out I really go for guys in sales, hasn’t worked out for me yet). He would brag about how much he ripped people off, but he was charming, fun, and incredibly good-looking. He wouldn’t accept tags of pictures with me, but that was okay because he just wanted privacy. Then guess what? He ended up cheating on me! I then found a host of other lies, including a “business trip” to visit an old flame and telling her friends to hide the pictures and deny his location. This led to both of us madly reading each other’s emails, texts, and Facebook messages and making accusations and yelling until it just became exhausting. I could never truly trust him to do the right thing.

A questionable moral compass is not something you want in a partner you will be depending on and asking for advice. Listen to your intuition here—whenever I felt something wasn’t right (like the day I woke up knowing I’d been cheated on), I was usually correct. Also, if you can’t stop snooping, maybe you need to explore that. You are literally looking for reasons to end it or start a fight, so eventually, if you’re looking, you’ll find something. You need to be with someone you respect and trust.


Despite my utter failure at dating, I still have hope (hey—learning what you don’t want is still an important lesson, right?). Be with someone who makes you happy, who makes you feel good about yourself. Go for unconditional love. I think, anyway. And good luck out there.

What’s the biggest mistake you made in the dating world? Comment or tweet us @litdarling

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