I often joke that while some people are serial monogamists—moving seamlessly from one LTR to the next—I should be labeled as a serial casual dater. While I have had several deeply meaningful relationships in my life, I have also spent quite a bit of time dating in the old-fashioned sense. That is to say, I’ve often found myself sitting across from a man I barely know, sipping coffee or a cocktail, making small talk while assessing our connection and my interest in ever seeing him again.
Over the years, I’ve had a rocky relationship with my dating life. At times I find it joyful and invigorating, and other times I’m fed up and convinced that I will never meet the right guy. Regardless of my own mixed emotions, going on so many first dates has taught me some profound lessons about finding peace with myself and others in and out of the dating scene.
Here are four life-changing lessons learned from casual dating.
01. I’ve learned to always expect the unexpected.
In my early years on the single market, I went into dates with some kind of expectation—positive or negative. I imagined what his sense of humor would be like, how he might hold the door for me, or the fireworks that would explode as his lips met mine at the end of the evening. These expectations would only heighten if the first date went well, and I’d start planning our matching Halloween costumes or worry about differences in our cultures or faith before I even knew his middle name.
I quickly learned that the first date was never what I expected, and I could never accurately predict the path our relationship might take. Dropping my expectations doesn’t just allow me to experience men as they are (not as I want them to be), but it also helps me pause and enjoy the surprises in the life I already have.
02. I’ve learned to not sweat the small stuff.
Dating is like interviewing for a job. You dress to impress, highlight your assets, share your goals, assess whether the partnership is a good fit, and part ways hopeful for a second meeting (or not). In dating, we are simultaneously interviewer and interviewee, and sometimes it’s just not a fit. In interviews, we tend to think that everything matters—from the color of our shirt to the quaver that slipped into our voice. The same is true in dating. We think “if only” I hadn’t ordered the spaghetti, texted him that stupid cat GIF, or asked where this was going—we would still be dating.
I’ve learned that when it’s right, it’s right, and the little things I obsess over won’t matter with the right person. Sending an effusive text to that guy you just started dating won’t ruin a good thing. A tipsy text full of kissy face emojis will not send the right guy running—unless it’s to your door the next morning with your favorite hangover remedy. And that goes for those little mistakes you make at work or in your friendships, too.
03. I’ve learned to communicate even when it’s difficult.
I’m not proud to admit that as a casual dater, I used to ghost on men I only briefly dated. My desire to avoid awkward conversations was stronger than the inner voice reminding me how awful it feels to be ignored without explanation. However, during my own agonizing hours spent avoiding looking at my cell phone for a text that never arrived, I learned that there is nothing more maddening than an information gap—and the worst kind of information gap is wondering what happened to the person I thought I was getting to know.
So I changed things. Now, I’ve realized all it takes is a brief phone conversation or even a text explaining that I don’t feel the connection I’m looking for, but I wish him the best. Men have thanked me for my candor, and one even asked if I had any single friends—if they were anything like me, he’d love to date them. But I don’t just utilize this strategy solely for dating. Whether I’m providing feedback to a student, asking my boss for advice, or counseling a friend, I strive to be open and honest in my communication. No matter our relationship status, we all should strive to put out into the world what we want to get back.
04. I’m constantly reminded that we are all just doing our best.
Dating is hard. It takes real effort and resiliency to continually make yourself vulnerable in the face of possible rejection. The greatest lesson I’ve learned through casual dating is that we as people are all in this together. The vast majority of us are looking for the same things: acceptance, connection, love, and a lasting, fulfilling relationship. In that search, most of us are acting in the best way we know how and with the best of intentions. But we are human. We screw up, we fail to communicate, we change our minds and have fickle hearts.
By learning to be gentle with myself and the men I date, I’m reminded that we all make mistakes in all facets of life, dating or otherwise. Yes, we should be held accountable for our blunders, but a healthy dose of compassion and reflection allows me to see life for what it is—our greatest and most enduring teacher.