I was never a fan of dating. I think I’ve shared that. I had little patience for the proverbial “games people play.” The flakiness, the leading on, the ghosting—I’m sure I’m not the only one who thinks it’s more than a bit exhausting. And then there are the pitfalls—the common mistakes we all make on the voyage to romance. I’ve found, through my experience, and that of friends, that there are two major dating blunders: the relationship that burns too hot, and the one that drags on but never really ignites at all.

First, the fire: I had a few boyfriends with whom we hit it off immediately. The chemistry I felt with those guys was off the charts. They were fun, attraction was intense, and our conversations were stimulating. And yet those relationships never lasted more than a few weeks. Some suddenly extinguished, with one of us abruptly losing interest, while others turned unhealthy and drama-filled very quickly.

Now, the fire-resistant: There were the long-term relationships that just weren’t meant to be. One of mine lasted nine years—living together for seven of them. My ex was a great guy. Truly, one of the kindest, smartest, funniest people I’ve ever known. He was handsome, too. We had many interests in common, and we loved each other. But the truth is, we really should’ve just been friends. Our relationship was comfortable, and easy-going, but it lacked passion. And at a gut level, I knew it from the very beginning—I broke up with him briefly three times in our first two years, and thought about it many more.

Are you familiar with the Greek myth of Scylla and Charybdis? They were two sea monsters who lived in the strait between Sicily and the Italian peninsula. Scylla had six heads and when a ship sailed too close to her, she'd eat a man with each head. Charybdis lived underwater, creating whirlpools that swallowed up entire ships, which she then devoured. They sat on opposite sides of the strait, so sailors navigating those waters had to be careful not to stray too close to one to avoid the other—either would lead to certain death.

Dating is like sailing between Scylla and Charybdis. On one side, there's the danger of falling hard and fast for "exciting" but tumultuous, unhealthy, or simply non-viable relationships. On the other, there's the danger of becoming complacent in a relationship that is adequate but has no deep sexual and romantic chemistry—a relationship with a person who could perhaps be a great friend, but not a lover. Both dangers lead to the eventual death of the relationship—one quickly, as if eaten by Scylla, the other slowly, as the ship sinks into Charybdis. Either death is bound to be painful.

Dating is like sailing between Scylla and Charybdis. On one side, there’s the danger of falling hard and fast... On the other, there’s the danger of becoming complacent.

What I’ve observed through the years I’ve spent sailing and watching others sail is that most people seem more drawn to one monster than the other. It may be that they’re so scared of the one that they always course-correct too far toward the other, or perhaps it’s just that they are blind to that one danger altogether.

If you’re currently sailing the dating straits, and find that you just can’t get through, take some time to discern which monster poses the greater danger to you. Do you fall too fast, pinning all hope on one person after the other, always thinking “this is the one” after five minutes of conversation? Or do you find yourself dating partners who are “good enough”—ones who tick off the major boxes but never feel quite right?

Be on the lookout for both Scylla and Charybdis. They sit close to each other, and getting past them requires self-awareness. If you find yourself constantly heading straight into the mouths of Scylla, learn to pace yourself. Accept that you simply cannot know that this one person you’ve met this time is most definitely the one. Get comfortable with conversations at arm’s length before you pull a stranger into a close embrace. If you find yourself drifting toward Charybdis, mindlessly (or perhaps anxiously) in a relationship that falls short of what you really want, don’t be afraid to break up; don’t stay in it simply because you don’t want to be single or can’t make up your mind.

I’ve faced both monsters, and I’ve lost to both. Thankfully, like in an old-school arcade, losing a life just brings you back to the beginning, and you get to try sailing the strait again. At one point I was even certain I had seen the dark screen of “Game Over,” but after a break I grabbed another token and got the game going again. In David I found the perfect co-captain for my ship, and together we’ve sailed into the waters of marriage (which have their own dangers).

Dating is frustrating. It is confusing. It is sometimes painful. But it can also be a lot of fun. And it can of course be fruitful—in addition to my husband, I initially met some of my dearest friends as dates. You can even see dating as an avenue for growth. So get to know yourself; figure out what poses the biggest dangers for you, and sail on.

Constantino Khalaf is a writer living in Portland. He and his husband, David, are the authors of Modern Kinship: A Queer Guide to Christian Marriage, a new book from Westminster John Knox Press. Available for preorders now.


Image Credit: Detail of Odysseus in front of Scylla and Charybdis, by Johann Heinrich Füssli. Public Domain.

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