Christian Singles & Dating

Confessions of a Dating Failure

  • Wendy Lee Nentwig Contributing Writer
  • 2005 1 Feb
Confessions of a Dating Failure

My name is Wendy Lee and I’m a dating failure.

There, I’ve said it. But don’t feel too bad for me. I’m not alone. And over the years I’ve learned to accept this deficiency and adjust accordingly.

While some women my age devoured books on dating, joined clubs to meet members of the opposite sex or appealed to the marrieds among us to set them up with eligible guys, I’ve settled into singlehood. I have a great group of friends that I spend my weekends with, a small church-plant that I’m very involved in, and family in California that I visit regularly. I travel, I’ve built a successful freelance writing career, and I bought my own home this past summer.
And there are other benefits to being single:

  • Unlike my married sisters, I can sleep in every Saturday without kids jumping on my stomach and demanding breakfast.
  • I don’t have to answer to anyone when I come home from shopping with yet another pair of shoes (“but these black boots have a slightly lower heel and the toe is more squared than my other pair!”).
  • I’ve never been forced to spend a weekend at a car or boat show.
  • Better yet, I’ve never had to sit through a Jean Claude Van Damme movie.
  • I’m blissfully ignorant of all the latest video games.
  • And my house? I’ve been able to decorate it exactly how I want. No making room for some guy’s collection of Star Wars action figures or his prized painting of dogs playing poker.

An Offer I Couldn’t Refuse?

But lately there’s been this annoying little question knocking around in the back of my brain: Maybe I’m missing out on something? It was around this time that an editor friend called to ask if I’d be willing to accept a challenge. Dr. Henry Cloud (you may have read a book he co-wrote with Dr. John Townsend called "Boundaries") had just finished a new book titled "How to Get a Date Worth Keeping." 

Well, I haven’t even been finding dates worth throwing back, so I’m not sure why my name came to mind. But this editor asked if I’d be willing to go through the book and write about my experiences with the program Dr. Cloud outlines. I was skeptical (I’m not much of “program” kind of girl), but I said she could go ahead and send me a copy of the book to look over. What could that hurt?

One of the first things that struck me was the tagline on the cover: “Be Dating In Six Months or Your Money Back.” I hadn’t spent any money so that wasn’t much of a promise in my case. Still, I couldn’t help thinking Dr. Cloud was pretty sure of himself. He obviously had no idea who he was dealing with. But then I read the book (wipe that smirk off your face. It was Christmas vacation and I had some downtime).

I have to admit I was impressed – and overwhelmed. Inside, there were no easy answers or false promises. Dr. Cloud wasn’t vowing to deliver the perfect man to my doorstep (like anyone would do that for $14.99!). He also didn’t say that if I’d just follow 10 easy steps, my phone would be ringing off the hook. Somehow that was comforting. Like most 30somethings, I’ve seen enough to know that if dating were that easy, everyone would be doing it. And most of my friends weren’t. Meeting someone you share things in common with, enjoy talking to and find attractive is about as easy as scoring front-row seats to a U2 show (speaking of, if you have extra tickets to their spring tour…).

Taking the Leap

I’m not sure that Dr. Cloud’s book will help me find that person (or any U2 tickets), but I do believe it will help me find some answers about my attitude toward dating and what I can do to change my situation if I really want to. So I’ve agreed to put my (nonexistent) dating life in his hands. I’ll be checking in once a month for the next five months and reporting on my progress. And Dr. Cloud has even agreed to look over my reports and offer personal feedback (as if this wasn’t scary enough, right?).

Maybe you’re looking for answers, too, or at least a guy worth sitting down for coffee with. If so, I’d welcome the company. Dr. Cloud can be your dating coach, too. Here’s all you have to do:

  • Pick up a copy of "How to Get a Date Worth Keeping."
  • Over the next month, read through Part 1, “What’s the Problem?” and then get started on the program.
  • Beginning this week, start keeping a log of how many new guys you meet (for me this will be a short list).
  • Finally, make a point to meet five new guys each week. Not sure where to start? Turn to chapter 7 in the book.

I admit, when I began reading about the program I gulped (meet five new guys a week?!), but Dr. Cloud has made it clear that he won’t take responsibility for how things turn out if I’m not willing to follow his plan exactly. And I’d hate to make him look bad after he’s been so willing to help so I’m pledging right now that I will stick to the plan. You have it in writing. There’s no going back. So I’m taking a deep breath and diving in. Here goes. Until next month…

"How to Get a Date Worth Keeping" is authored by Dr. Henry Cloud and releases this month from Zondervan Publishers.  Based on over ten years of personally coaching singles on dating, Dr. Henry Cloud shares his proven, very doable, step-by-step approach to overcoming your sticking points and getting all the dates you could want.