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The 6-Month Dating Experiment

The 6-Month Dating Experiment

Let me be frank: It’s hard to write about your love life when there’s just not much going on.

When I read Henry Cloud’s book How to Get a Date Worth Keeping: Be Dating in Six Months or Your Money Back, I was confident that I’d be dating in no time. OK, I didn’t expect to be asked out as often as my friend Apryl, who had seven dates lined up for last week alone. But I anticipated a fair amount of success.

That was five months ago, and I haven’t been on a single date yet. It’s tough to follow Cloud’s advice to “go out with almost anyone once, and maybe again” when nobody seems to be interested.

“The next day I woke up lying to myself, I feel fine.”

Sometimes I use that as ammunition to beat myself up. One night last month I pitched a bona fide temper tantrum. I sat in bed with my quilt, cat and journal, writing the following words:

“Why do I inspire such lukewarm feelings in men? Why am I the girl with whom they flirt, but refuse to take the next step? Why don’t they want me?"

I know that in asking that, I seem to be seeking my worth in the eyes of men. Know that I’m fully aware that my value lies not in some man’s opinion, but in Christ’s ineffable love for me.

That doesn’t mean these questions don’t cross my mind. The other night two of my close friends and I were discussing all the guys who had crushes on one of them while we were in college. I silently tried to turn the question around on myself, but instead of coming up with an answer, I drew a three-and-a-half-year-long blank.

I can’t name even one guy who was interested in me then, and I want to know why. Was I unattractive? Too talkative? Too insecure? Too much of a goody-two-shoes? Was it because other girls were more athletic or more exotic or smarter than me? Do I like football too much? Am I not godly enough? Were my clothes all wrong? Did I act too maternal?

Is there something wrong with me?

It’s OK if I am, as my sister termed it, “fundamentally undateable.” At least, I think it’s OK. But could someone please let me know, so I can avoid (or accept) being the girl all the boys flirt with but wouldn’t dream of dating? Please …

“I had been taught love is a vice.”

I don’t know why I let the past get me down. After all, it’s been three years since I left college. And most days, I really don’t care that this whole “program” hasn’t been working for me. I’m 24 years old—I’m not in a hurry to settle down.


The truth is I want to be someone worth fighting for—not just for one date, but for a relationship, and someday for a lifetime. I want to risk letting down my guard. I want someone who is willing to love me when I’m “not myself” (to borrow John Mayer’s phrasing). I want someone who is worth the risk of vulnerability. I want someone to believe I’m worth the fight.

And yet Jesus is already all of those things. Why do I struggle to believe that? And why do I make myself feel guilty for desiring some earthly, though imperfect, reflection of that?

“The vice spins and the ice turns to melt.”

I’ll admit that as I’ve seen Cloud’s advice prove unsuccessful, I’ve started to give up a little. There are still weeks when I met my requisite five new guys, and I’ve even toyed with the idea of an online dating service. (Sorry, Henry—as much as I appreciate your advice, I just can’t bring myself to go through with it.)

So I’m five months into this experiment, and what have I learned? Well, I have improved my friendships with guys. But moreover, I’ve noticed that this ice princess is starting to melt a bit. Because I usually don’t believe anyone would be interested in me—or more specifically, that anyone I like could be interested in me—I can be stand-offish and cold. I try to pre-empt rejection.

One of my guy friends recently said to me, “You’re the sort of girl that boys would like to be interested in, but if you’re all ice queen, what are they supposed to do?” He has a point, I think.

I’m fighting the urge to be aloof around boys I might be interested in, as though I don’t care if they come around. I’m avoiding the “I won’t call you, you must call me” game. (What can I say—I’m a Southern girl. Mom taught me to let boys do the calling.)

Sometimes I even flirt a little bit!

See, it’s nice to feel like a girl, like maybe all these years of not dating are a fluke. Like there’s something attractive about me, whether it’s my hair or my personality or my smile. My friend Heather says that’s kind of the point of all this—just to remember what it is like to be treated like a woman. She says (and I agree) that being looked at like a woman is exhilarating, because that’s the nature of being worth it—it’s a reflection of the church. That’s the whole point of it.

That, and to learn not be so ice-cold that I’m intimidating when the right guys come along.

I’m still working on that, I suppose.

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