In today’s world of fast-swiping dating apps, relaxed social norms regarding premarital sex and cohabitation, and new permissive social norms regarding sex-positivity, kink, and alternative relationship configurations, it should hardly need stating that people are dating around more than ever. Thus, I’m not going to waste time making an argument for the acceptability of dating around. Instead, I’m going to show why dating around is not only healthy, but a set of skills and habits that should be actively practiced and refined, akin to working out, eating and sleeping well, and managing your finances.

The Benefits of Dating Around

Affection, sex, and relationships are healthy, there’s no doubt about it. Research has demonstrated that these activities regulate our hormone levels, leading to happiness, stress reduction, healthy risk-aversion, reduction in feelings of loneliness, etc., etc. This shows at least that entering into and maintaining relationships is better than not being in a relationship. But what about having a series of relationships, or having multiple relationships in parallel (assuming we’re being ethical about it)?

The Upward Spiral of Experience

Too often people unwillingly end a relationship and feel single again, back where they started, a failure. If we’re talking merely about our relationship status over time, then it does tend to resemble a circle: single > dating > relationship > breaking up > single again, and round and round we go until we “find the one” who ends our search for the perfect match.

But if we approach relationships from a mindset of learning and growth, then we’re never truly back where we started. While our relationship status is cyclical, our relationship skills improve and our overall experience elevates to new levels. Thus, the cycle of relationships is, in reality, an upward spiral. Each turn brings new insights. Each return to a particular state is different because we are different; the entire experience is different. It is never a failure; it is a constant moving forward. It’s like returning to your childhood home and realizing how short everything is; the home is the same as it ever was, you’ve grown taller, and thus your perspective has shifted forever.

Widened Experience

Being overly selective without prior experience is often frowned upon in other areas of our lives. Think of picky eaters or music snobs. Our instinct is to present new tastes to these people to help them appreciate more of the world. So, too, it is with our sexual and romantic partners. Without a wide sampling, we simply cannot know what else we might enjoy. Being selective too early on in life artificially restricts the types of experiences we can have and makes it more likely that we’ll have difficulty finding better matches and possibly settling for less than we have the potential to love.

There are a wide variety of people, of sexual preferences, of relationships styles, even if we’re being fairly vanilla about it. There is value in a fling—feeling that intense New Relationship Energy and then allowing it to pass. And there is value in finding someone who pushes your sexual boundaries and exposes you to new pleasures you didn’t know possible. These are not one-time, throwaway lessons. Rather, these lessons are carried with you throughout your entire life, and they form a foundation upon which yet wider experiences are built upon.

A Basis For Comparison

Standards are sets of preferences brought about through cultural programming, second-hand experience, and, most importantly, personal exploration of a person’s unique interests. The only way to build a robust set of standards, to know what you truly enjoy or shy away from, is to go out and test those standards.

In this way, you may realize that standards are not a list; they are not checkboxes that you tick for each person. Rather, they are dynamic and changing. What you may not appreciate in one person, you may appreciate in another. There are some combinations of traits that work well together under certain conditions, yet under other conditions or broken apart you may find those same traits repulsive. The point is that you truly do not know until you have multiple partners to test against.

On One-Itis and Breakups

This article should in no way be construed as arguing that love at first sight or soulmates are impossible. These concepts are possible, but are strikingly rare. My brother and his wife are good examples of this: a model relationship built upon love, trust, understanding, and a healthy acceptance and mockery of each other’s faults. They were each other’s first true relationship, and many years of marriage and several children have not broken the spirit of their joy for each other.

But usually people fall into the trap of believing the old trope of “a relationship takes work.” They believe that they should try as hard as possible to make their current relationship work, even when all signs point to fundamental incompatibility. Relationships do take work, but that work should be joyful. When that work harbors resentment, it’s time to consider ending the relationship. Thus, we practice breaking up.

Breaking up is not the bogeyman that it is made out to be. This, too, is a healthy learning experience in which two people find their boundaries and how far they can stretch and compromise for each other before the stress of it breaks them, and discover how to resolve their differences with an amicable separation, and learn to process their emotions in a healthy way and how to recover from a sense of loss. These are important lessons in life! And those lessons are generalizable far beyond romantic relationships, into childrearing, professional relationships, and personal relationships with oneself.

Patterns and Anti-Patterns

As our experience is widened, it is also deepened. I encourage anyone who is afraid of falling in love at the risk of heartbreak to embrace that possibility of heartbreak. Only by allowing ourselves to fall deeply for someone and feel the pain of it at the end, and choose to fall deeply again, can we learn how and when to be vulnerable. And by allowing for that kind of deep connection, we progress far enough into relationships that we start seeing the patterns and anti-patterns.

Patterns and anti-patterns are those experiences that seem to happen time and time again:

  • New Relationship Energy: those magical 3-6 months after meeting someone when everything seems too perfect and serendipitous, and you hope it will remain this way, but it doesn’t, which reveals…
  • The Passion/Compassion Curve: that spike of passion at the beginning of the relationship that fades over time, followed by a slow-growing yet much deeper sense of connection with your partner
  • Jealousy and Attachment: the clinging on to your partner as they are, fearing change or withdrawal, fearing their association with other people or things in their lives, knowing what manifests the emotions and how to process them in a healthy way
  • Emotional Processing: how you deal with your emotions—do you stifle them until they explode, do you let them take control of you; or do you learn to come to terms with them, and allow them to teach you lessons as they pass you by?
  • And many more…


Some people never seem to put energy into dieting or exercise, and yet they’re perfectly healthy. The same is true of relationships—for some people, they meet their first love early and happily remain at their side for the rest of their lives. But for the rest of us, we do need to consider how we date, just as we consider what food we eat and what sports will keep us moving around.

There is no other way to learn the deepest lessons of relationships except by exploring as widely and as deeply as possible, as often as feels healthy for us. And by doing this early in our lives, by carrying those lessons with us forever as we traverse the terrain of relationships, we promote healthy relationships for ourselves, and bring about emotional and physical health as well.

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