The Tale of the Big Hill…a.k.a. What’s Taking This Dating Optimism So Damn Long?!?

I get lots of questions from those of you who’ve read the book and want some extra guidance. This week, I got two of nearly the exact same question so I thought it was time to address it stat. The question is: “I’m being optimistic. I’m staying positive. And yet…no one. What the hell is taking so damn long?”

In response, I want to tell you…

The Tale of the Big Hill

This is Peru, not Sea Cliff. But a hill's a hill. (Image: Amy Spencer)

I grew up on a steep hill in Sea Cliff, and when it was time to learn how to use the stick shift in our Volkswagen Rabbit, my parents took turns teaching me. On my Dad’s turn, we headed up the hill toward town as I wondered which street we’d turn onto at the end. But then, at the very top of the hill, my Dad shouted, “Stop!” After I did, he said, “Okay, let’s go.”

Now, I don’t know if you’ve ever driven a stick shift, but when you let go of the brake, the car doesn’t sit still. It rolls backward—fast. The only way to get the car moving forward is to master the pressure as you let up on the clutch and tap the gas at the same time. It’s an art form. And at the top of a steep hill, it’s also a heart attack.

After four tries, six tries, ten tries, I started to cry. “This isn’t fair,” I said. “I can’t doooo it!”

“Yes you can,” he said.

“I can’t!” I said, rolling backward on try number eleven. But my Dad didn’t give up on me and wouldn’t let me give up on myself. Instead, he told me how important it was that I learn how to do this. On try twelve, I started getting the hang of it. By fifteen, I did it! Perfectly.

“Do it again,” he said. I did it over and over and over again. Sometimes poorly, sometimes perfectly, but the more I did it, the more I nailed it. And when I got home that day, I ran beaming into the house, shouting how great I felt. And from then on, no hill frightened me. Those small humps I used to think were tough? “Pfft, cake.” I became fearless in that car; no road was out of bounds, no stoplight on any incline made me flinch. Years later, I was the one of my friends in San Francisco who had to hop into the driver’s seat to parallel park our car on the hill because no one else could do it. This is the gift my father gave me. And this is the gift that life is giving you.

Dating, sometimes, can feel like torture. It can feel like you’re sitting at the bottom of a very big hill with no tools to get to the top, no energy to climb it, and no assurance that once you get there you’re going to like what you find very much at all! But the hill is a part of your journey to that great relationship. If you can accept that your life is about becoming the best of who you can be for the right relationship, it might be easier to accept that hill. Because once you climb it—through the sucky relationships and the lonely nights and the failed blind dates and the jerks who don’t text you back—you will get to the summit strong and proud and really ready for love.

Part of the essence of dating optimism is that it’s not just about taking the short cut—riding the tram up the hill so you don’t have to walk or drive it—to someone you can settle down with. It’s about the hill too. As I talk about in Meeting Your Half-Orange, the optimism is about the whole journey. You may be tired of the journey, but it’s vital in teaching you to appreciate your life and the people you meet, and to become the person now who you want to be in the right relationship later.

Sometimes life makes our hills longer because there is more for us to learn on our way up. If I hadn’t climbed my dating hill before I met my husband, I never would have appreciated all the things about him I didn’t know were important and been ready for marriage with him. The hill is readying you for love in ways that you don’t know yet. That’s what’s taking so damn long. I think life gives us the right person when we’re good and ready enough to appreciate them. You may have another person to meet, another lesson to learn about yourself, another lame date with a player to appreciate how valuable a “good guy” really is. I know it’s hard, I know it sucks sometimes, and I’m glad you’re staying positive when you can. Just remember: You might meet the love of your life tomorrow. So don’t you want to be in a place of gratefulness, calm and acceptance when you do?

Here’s to your hill. Life isn’t giving up on you, so don’t give up on yourself.

You might also like:

The Motorcycle Lesson

Big love,