15 Lessons I’ve Learned While (Casually) Dating

I’ve never been good at maintaining relationships; and although I consider myself lucky to have been in love a few times, they all seemed to fizzle out as quickly as they began.

I was recently inspired to pick up the cult classic Modern Romance a few weeks ago. I read the book ages ago, but I couldn’t relate to it at the time since I didn’t have an extensive dating history. Relationships usually fell into my lap, and I never thought too deeply about what I needed from a partner.

Following a toxic breakup over the summer, I went on a serial dating binge. I realized I didn’t know myself as well as I thought I did, and I still had a lot to learn. In response, I went on countless first dates to try to understand what qualities I wanted in a significant other. Some were fantastic. And some are still stories I tell my friends (100% guy).

In the book, Ansari breaks down dating in the 21st century to a science—everything from the art of taking pictures for your online dating profile, to linkages between social media and cheating, to how to initiate the first text. A lot of the book resonated with me—namely because it made me more aware of attitudes during my own experiences that I didn’t recognize before.

One of the most significant takeaways for me when I reread Modern Romance was the concept of choice: we have more options than any other generation in history. This also makes the idea of “settling down” really difficult—there’s always going to be someone smarter, funnier, and more talented than the person you’re dating. On some level, I think falling and staying in love is a choice; casual dating can be a gateway in understanding how to solidify that choice so by the time the right person does come along, you’ll know.

I’ve found casual dating has its pros and cons: the pros including being able to meet new people and adapt to new interests and cons including the amount of work and time invested required (sometimes even more work than a part-time job). I’m not an expert by any means; but I wanted to share my 15 takeaways inspired by both the book and my experiences:

  1. Don’t compromise your values to make a relationship work. It’ll only breed resentment. At the same time, you need to have a strong sense of self too. You can’t expect to know your boundaries if you don’t quite understand who you are either.
  1. Be with someone that encourages you. If they aren’t willing to support you in the way you’d like to be supported, move on. Part of being in a healthy relationship is learning to speak each other’s languages—you have to be willing to do so too.
  1. Take time with a grain of salt. Time invested isn’t necessarily a reason to continue to date someone.
  1. Everyone has flaws and bad habits—even you. It’s just a question of which bad habits you’re willing to accept and tackle head on.
  1. One of the most challenging parts of casual dating is how quickly people can phase in and out of your life—especially coming from someone that has difficulty letting go of long-term relationships. There are some I’m still friends with and others I’ve never spoken to again. Just keep your mind open to possibilities and manage your expectations.
  1. There’s rarely such a thing as the right person at the wrong time. If the timing’s off, that’s probably an indicator that they weren’t the right person for you after all. A relationship is about sharing priorities.
  1. Tread lightly with friends that want to set you up with their friends. Most of the time, your friends only know that person as a friend and not as a potential boyfriend or girlfriend. The date in question might be a fantastic friend, but simultaneously be a difficult person to date.
  1. This is going to sound like a blatant contradiction to #1, but keep in mind everyone comes from different backgrounds, cultures, and experiences. Your worldview is one among billions. And although sharing values is important, you’re usually better off trying to understand what their intention is rather than marking them off as incompatible.
  1. You’ll learn something from every date you go on. One tuned me in to my now favorite podcast. Another taught me to pursue what makes me happy, even if it’s the road less traveled. Another inspired me to step out of my comfort zone. If you feel like you haven’t learned anything, you probably haven’t vetted enough beforehand. Quality trumps quantity. Dating doesn’t have to be a numbers game (unless that makes you happy, then by all means carry on).
  1. “I’m too busy” usually means “you’re not a priority right now.”
  1. As tempting and easy as it can be, don’t ghost on people even if the date goes south. I used to be pretty guilty of this. Make your intentions clear from the get go—and if you change your mind later, that’s completely okay! Just don’t forget there are real people behind your touch screen. Take it as a learning lesson to be able to communicate more thoroughly what you want and need.
  1. Lock him down if he likes the same memes as you.


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  1. Staying friends with someone you’ve dated is a lot of work—or least it is for me. I’ve never been “friends first” with an ex-boyfriend, so taking the time to create a foundation of friendship or maintaining any form of contact after the relationship ended has always been a no go. If you’re willing to try, give yourself space to mourn the end of the relationship and then work towards being friends. It’s a process, but it’s possible.
  1. If you want to date a quality person, you must be a quality person yourself. I see so many men and women enter a relationship with the expectation that the relationship should fill in a gap that’s missing. I don’t buy that. I think a relationship should be something that adds, not fills, to the already amazing life you have. As cliché as it sounds, you should be happy and secure being on your own instead of relying on someone else to decorate your soul. Sometimes you need to explore yourself before you explore your partner self.
  1. I’m not sure if it’s just me, but once a relationship ends, I have a tendency to delete everything (we call it the nuclear option among my closest friends). Gifts, letters, photos are all fair game for deletion. I used to disavow the relationship of any meaning and downplay its significance in my life. Although the petty queen inside me probably won’t stop deleting things, in retrospect, denying the significance of those relationships was immature. Now I’m thankful for everyone I’ve had the opportunity to date and want happiness for every man I’ve shared a relationship with. They’ve all given me better insight on what I want and how to improve myself into a better partner for the next. And that’s okay—because the ceiling of your previous relationship will be the basement for your next.

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