dear hilary: the leap

Dear Hilary,

I have loved the same boy for most of my life. We’ve been dating now for two months, and he’s crazy about me and I can tell, but he’s reluctant to get more serious in case there’s somebody else who is “The One” for me down the road. I don’t think there will be, but I don’t know how to tell him so he’ll believe me. I think this might be a forever kind of love. But when do we know for sure? When does it just become time to take the leap?


Dear Cliff-Dweller,

When I was 17, the movie Enchanted came to the big screen. A sweet movie, one that cleverly and wonderfully plays with other Disney stories, a redheaded heroine, the city of New York… I loved it.

At the very end of the movie Carrie Underwood sings this song, “Ever After.” I used to imagine (I’ll admit it, because this is a place to be real) that I was Carrie Underwood singing that song. I used to imagine that “The One” would sweep into my life and play opposite me in a slightly-more-but-not-that-much-more-realistic version of Enchanted. 

Haven’t we all done that, somehow? We wait for the sign. We wait for the marvelous, the extravagant, the moment when there is nothing for it but to burst into song in the middle of a crowded street and hand out roses. We all want a One, and we all want to know for sure. We think that finding “the one” will give us the permission to be extravagant with our love. To proclaim and sing it, Carrie-style.

But I wonder if we, in our waiting for the big sign, we end up more afraid than we should be. What if that wasn’t the sign? we ask ourselves driving along country roads. Or what if there is someone else, in a different state/country/zip code, in a different college, with a different life story… we write in our journals. I wonder if he or she is really everything I think I want. I wonder if I should be as committed to this as I want to be… I wonder, I wonder. 

We could wonder ourselves to death waiting for someone to come in with a pot and a wooden spoon, clanging away, “The one is approximately 2.4 miles and 3 months away!”

If you want to know anything, you have to leap.

You’ve entrusted a big thing to me – this question about love – and I don’t take it lightly. I don’t think we are meant to be thoughtless or hasty before we leap. I don’t want to tell you or your boyfriend to do that. Ask each other hard questions. Ponder together what this thing is between you, and what you think it might or could become. Fight, and laugh, and even spend some time worry and pleading and joking and explaining and listening… and a million verbs.

All the million verbs point to the bigger point, though: live it. 

That’s what the leap is about. You won’t know before you go whether this is “the one.” You won’t know what kind of gift you are to each other. You won’t know if it is a forever kind of love. I can’t promise you that.

But I can promise you that when it comes to love, the only learning is in living. I can promise you that if you leap, whether you are a forever love or a season of love, whatever the nature and shape of your story, it will be lived. We can wonder alone in a dark room with the “Enchanted” soundtrack playing, asking for the sign that will make us sure that we are right about who this person is and what they are meant to be. And I think there is a special kind of love I have for those days, in all of our stories.

But I wish the fullness of leaping for the two of you. I wish the hearts that you’ll help expand in each other. I wish the bigger story, the one of unknowns and discoveries and all those million lived verbs.

There is a glorious kind of life in the leap together – wherever you land.



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