I was sitting at a local happy hour, sipping wine with a friend. Young and recently out of a relationship, my friend has never casually dated. Her previous serious beaus all blossomed from friendships. As the pinot flowed, she divulged that a strikingly handsome stranger had approached her in a bar, offered a stellar pickup line and his number, and she was hesitant on how to proceed.
She looked at me, with all my years of dating experience, and asked, “So, what do I do?”
Honestly, I’ve asked myself no-brainers like that a thousand times. Sadly, too often in my past, I’ve overcomplicated the answers. By taking dating too seriously, I’ve shot myself in the foot, spent too much time in my head, and ended up standing in my own way. But after making some serious changes in my dating life, I’ve realized that loosening up and taking dating a little less seriously can yield better and, surprisingly, far more serious results.
In so many words, this is the advice I shared with my friend:
01. Get to know your dates organically.
When I was young and newly dating, I treated each date as if he were a possible future husband. As a result, I dumped a whole lot of information on him that he didn’t necessarily need to know—at least not yet. I felt the need to share everything about myself. Immediately. My insecurities would tumble from my lips, and I imagined them filling the space between us. Not so. Rather, I often pushed a date away as I overwhelmed him with my overzealous sharing.
Sure, someday someone will share my hopes and dreams and help me carry my burdens, but that will be long after our first date. Let the information flow naturally. Let him ask questions. Let him be intrigued. Let it take time.
When you see the first date as an opportunity to simply have fun and learn about the other person—as you match the level of sharing to your level of emotional intimacy—you’ll have more enjoyable second, third, and fourth dates.
02. Scrub your checklist.
Checklists. We all have them—and some of these requirements are legit (e.g., morals, values). But when we take dating too seriously, there’s a tendency to become a tad idealistic and aggressive in our checklists. Sure, some qualities are important, but lengthy checklists often veer toward the superficial—height, profession, or even neighborhood. I’ve known city-dwelling women who won’t consider a man who lives in the suburbs and others who dismiss a man who fails to reach six feet tall.
You see, we think we know what (and who) is best for us, even when life consistently proves us wrong. We build up the perfect partner in our minds and look for him in everyone we meet. So when a man fails to immediately meet our criteria, we never give him a chance. Perhaps the guy who’s an inch shorter than you would make you laugh until your stomach hurts, and that man with the house in the suburbs? He’s probably grounded, financially stable, and would love the opportunity to cook with you in his giant suburban kitchen.
Aside from some core nonnegotiables, take a few risks and watch your dating life expand. I promise you’ll learn more about what you truly want in life and in a partner when your nose isn’t stuck in your checklist.
03. Open up to possibilities.
I love labels and boxes and all things organizational. I used to try to label the relationships in my life, too. I agonized over the status of a relationship after five dates or unilaterally decided that the new girl at work was just that—a new girl at work, not a potential new friend. And that guy at the gym? Just a casual acquaintance. But the truth is, people defy categorization, and relationships with the people in our lives are fluid.
When you loosen your grip on your dating life, you’ll see that the possibilities are endless. That new girl at work might become a dear friend who introduces you to the love of your life, or that casual friendship with the guy at your gym might be the start of a slow burn that will grow into lasting love. You don’t need to label everything in your life—you need to live it, and taking dating less seriously will allow you to do just that.
04. Give yourself permission to have fun.
There are so many elements of your life that you must take seriously, but going on a first or second date isn’t one of them. Loosening up leaves you free to have fun. To enjoy his company, the coffee, the dinner, and the wine. To laugh when his jokes are funny, to flirt unabashedly, and to see each date as an adventure. We often lose sight of what dating is all about. And it’s this: It’s about connecting with another person, sharing who you are while learning who he is, and enjoying each other’s company. When you don’t take yourself or the date too seriously, you’ll quickly find yourself having the best dates of your life.
So go ahead and give him your number, show up, ask questions, listen to the answers, and enjoy every second of it. Taking dates more casually at first will allow you to enjoy your time as a single person, and I guarantee you, you’ll see some serious results.