How Casual Dating Opened My Heart to Love

“Hopping from one relationship to another is not the way to find love. Slow down and give love a chance to find you.” ~Unknown

When I was younger, I was a serial monogamist.

I did the math recently and it turns out that once I started dating, I didn’t spend more than two weeks single at any point.

Then, after the end of my most serious relationship ever, I had a moment that changed everything.

My boyfriend and I hadn’t even been together a whole year, but I really thought he was the one, my soul mate. We had so much in common. We seemed to see eye-to-eye on everything. But then a stupid fight about birthday candles somehow blew up and ended our relationship.

I remember just standing behind the window the morning he left with a box of books under his arm. It was the end of October, and we’d just had the first snowfall of the year.

I kept thinking about the last Christmas we’d spent together, how he’d taken me snowshoeing for the first time. Our breath crystallized in the evening air.

Then I realized that that wasn’t actually him. That had actually been my previous partner before him. All my relationships had begun to blur together so I couldn’t tell where I ended and they began.

The idea of going out there again, into the cold dating world, seemed impossible. Even if it worked out, wouldn’t it just end up the same way?

I felt trapped.

When you keep getting what you think you want and you’re still not happy, you have to start asking yourself, what am I doing?

So instead of firing up Tinder, going to the bar, or texting someone, I made a different choice. I simply waited.

I realized that what was creating problems in my relationships wasn’t the fact that I couldn’t find my perfect match. It was my attitude.

I felt like I couldn’t be alone. I didn’t want to deal with life as a single woman. But the real problem was that I looked at life as a search for this idealized perfect partner that probably didn’t even exist.

Embrace Strength Over Fear

When I was jumping from relationship to relationship, I was making my decisions based on fear—I was trying to avoid pain rather than trying to embrace love.

I sometimes wonder how many of my relationships were twisted toward jealousy, insecurity, and conflict. How many people did I date that were simply wrong for me out of a fear of being alone? 

And how much time did I waste clinging to those men, as if they were my only hope for happiness, when I not only had the power to be happy on my own, I could easily find other people to date if I tried?

Stop me if you’ve heard this one: There are plenty of fish in the sea. This is a cliché for a reason. There really are so many people out there that you could date a different person every week and never run out.

That’s not to say that we need to jump from superficial relationship to relationship. It just means we don’t need to suffocate our relationships with fear because we can trust that we’re strong enough to be alone and we’ll always have options for relationships in the future.

The Casual Dating Difference

Casual dating was always something I had avoided like the plague, but when I thought about it, I wasn’t sure exactly why. It was one of those things that you put into the category “sounds like fun, but it’s not for me.”

But after a few months of being intentionally single, I started to get lonely. I was proud of taking the time for myself, and I knew I didn’t want to dive back into a relationship just yet. Still, deep down, I know I thrive when I’m out in the world, meeting people, and getting to know them.

I knew I wanted to get back out there, but I wanted things to be different.

What Exactly Do I Mean by Casual Dating?

One reason that monogamy is the norm is that it’s something we can all wrap our heads around. Casual dating is a lot more vague because it means different things to different people.

I came at casual dating from a place of complete ignorance. Rather than being a drawback, this allowed me to create a definition of casual dating that worked for me.

Basically what it comes down to, for me, is non-exclusive, ongoing relationships with one or more people. I’m all about communication, but I prefer seeing people face-to-face. This means no texting, check-ins, or endless social media interactions.

I sometimes felt rude or callous putting these ground rules out to someone I’d just started seeing, but I place a lot of value in honesty, openness, and mutual respect. I found that, while this may have been a difficult conversation to have, it saved confusion and hurt feelings down the road.

I made sure the people I was seeing understood that this probably wasn’t going to lead to a more traditional relationship because I still wasn’t ready for that. I wasn’t playing hard to get so that they had the chance to win my heart. I was enjoying their company and getting to know them, without any pressure on how our relationship would evolve—or if it would at all.

This actually enabled me to be more fully present with the people I was dating. By simply being open to new possibilities without clinging too tightly to any one person or relationship, you’re able to build something beautiful, moment by moment—whether this is with several people, only one, or even just yourself.

Casual dating can be a path to self-discovery and lead to a deeper, more healthy relationship if you do eventually decide to commit to one person.

The Casual Dating Checklist

1. Have clear intentions.

While many people choose casual dating to avoid having difficult conversations, this can lead to a negative experience for both parties. I advise you to be open with the people you’re seeing about what you’re looking for. This means figuring out what it is you want and what you have to offer another person rather that letting it go unsaid. First and foremost, this means being honest with yourself.

2. Slow it down.

Casual dating gets a bad wrap because some people think it’s synonymous with “sleeping around.” While there’s nothing wrong with that, as long as you’re being safe and honest about your intentions, you can date casually without hopping right into bed.

In fact, when you’re dating someone casually you tend to see them less frequently, so things can unfold more slowly and naturally than with traditional relationships.

Beyond just sex, adopting a slower pace with casual dating can actually create a stronger and more real bond than strict monogamy. You’re less likely to get caught up in the “rush” of a new relationship and will instead be focused on actually getting to know them as a person.

3. Explore your options.

One of the biggest appeals of casual dating is the freedom it gives you to date outside of a narrow type. When we’re looking for someone to spend the rest of our life with, we tend to be less forgiving, accepting, and open to new experiences.

With that in mind, make sure to date new and different people. Be open to invites and attention from people you’d normally steer clear of.

4. Understand what you want and need.

Casual dating is about finding out what you want through experimenting so you don’t have to have things all figured out going into it. But make sure you’re being fair to yourself in these encounters. Don’t settle for people who mistreat you. Just because it’s non-traditional, doesn’t make you any less worthy of respect.

5. Know when things have run their course.

Whatever the circumstances, it’s good practice to be clear and honest with the people you’re seeing. Instead of ghosting, tell them how you feel. A lot of the problems that come with casual dating are in how it blurs lines between dating, sex, and relationships. When in doubt, speak out and make your feelings clear. If you’re going to end it, do it without any ambiguity.

And sometimes, things don’t have to end. I’m happy to say that, after a few years of keeping it casual, I’m back in a more traditional exclusive relationship.

At first, he was just one of several people I was seeing. We spent more and more time together and before long, I realized I wasn’t interested in dating anyone else. I just wanted to get to know him and only him.

While we are monogamous now, we did it by choice rather than obligation. This happened naturally and we both agreed upon it rather than it being simply the default.

What we have feels more real than anything I’ve had in the past. And I know that if it ends, I’ll be able to move forward. While I love him, and I love what we have, it’s finally loving myself and my freedom that has allowed me to be happy.

About Jessica Boss

Jessica Boss is a relationship coach and writer who helps people to create their own ideal love life with a basis of self-love and honesty. She is a staff writer for LoveLearnings.com where she dispenses advice and guidance on a variety of topics including marriage, conflict resolution and breakups.

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