Book Review: How to Get a Date Worth Keeping


Since I’m happily married, why in the world would I read a book about dating? This is a legitimate question and the short answer is because I’m reading a book a week and need a break from narratives.

The longer answer is, I’ve been intrigued by How to Get a Date Worth Keeping by Dr. Henry Cloud, because a friend of mine coaches singles in this program with remarkable, as in “near-perfect,” success. Her approach fascinates me, plus I work with and have dozens of single friends; and so I thought I should see what wisdom I could glean.

My final takeaway is the book was not merely engaging, it struck me as true. That said, I imagine Dr. Cloud’s approach could be met with resistance and skepticism for one overriding reason: he insists that people who aren’t dating well are personally responsible for their situation.

And by “insists” I actually mean “INSISTS.” All caps. No hedging.

He makes statements like these:

“Our lives are not just about the ‘outside’ circumstances…We participate in our external circumstances.”

“Philosophers over the years have referred to this responsibility for our own life as ‘existential responsibility.’ We do not cause our existence, but we participate in it, and we are responsible for dealing with it and, as a result, have a hand in creating and changing it.”

If you don’t want to own the dating life you’re currently living, if you blame the quality of men or the unavailability of women, you’ll hate this book. Cloud doesn’t budge an inch on his perspective. He argues, very convincingly, that “the ability to attract others comes from things going on inside them” and dating is “much more about your ability and eligibility.”

If you’re single and reading this book, you better wear your big-boy or big-girl pants because Dr. Cloud gets real in a hurry.

After some prefacing about the proper mindset of dating (to get to know people, to learn about yourself, to grow in skills, but not explicitly for marriage), Dr. Cloud jumps into the uber practical part of the book, aka “The Program.”

The Program is all about application and its prescription is enough to make any single person shudder because it’s highly specific. His theory is single people “reap what they sow,” so they need to PRACTICE sowing. He breaks the program into 18 quick and practical chapters. The titles of the chapters will give you a sense of what I’m talking about. Here’s a selection:

  • Keep a log
  • If you say “there are no good prospects,” you don’t get it
  • Meet five a week
  • Change your traffic pattern
  • Get over the stigma: Join a service
  • Get your team together
  • Don’t limit yourself to a type
  • Check your expectations at the door
  • Go out with almost anyone once, and maybe again
  • Be yourself from the beginning
  • Keep your boundaries and don’t settle

Each chapter calls out old habits to ditch and new approaches to try. He writes about making eye contact, why you should ask for help, and the necessity of changing routines. When he advocates dating outside your typical “type,” he does so with an eye on stretching expectations and establishing greater openness.

His logic is ridiculously solid, but equally challenging. In fact, I can’t help but see a catch-22 scenario; those who need to be more open to new ways of dating are too closed to find new ways of dating. How do you get out of the cycle?

Dr. Cloud gives an answer which is to “stop trying to find that person and focus on becoming that person.” This advice overlaps with the more elegant sentence found in The New Rules of Love, Sex, and Dating which is, “to become the person you’re looking for is looking for.”

Again, his approach is to place the responsibility for change at the doorstep of each individual. He tackles why you “attract the wrong people” and where you need to establish healthy boundaries. He calls men and women to grow up and become equal with others.

“If you want to find a good relationship, grow up and take hold of adulthood. Stop putting yourself in either the child or the parent position with others. Value your thoughts and opinions and speak your mind, but also respect the opinions of others. Give up wanting other people’s approval, and stop giving them the power to make you feel good about yourself. Give up judging others and allowing their judgments to affect you.”

Over and over again Dr. Cloud writes how dating takes initiative, effort, and work just like anything else in life. However, the message is also that dating should be fun.

“…dating is not supposed to make your life miserable. Dating is about growing – spiritually, personally, relationally – and having some great experiences. Don’t let dating get you down, and don’t put too much stock in any one date or any one person…Decide in advance to have a good time with this adventure.”

I can see why the program works for those who are open and courageous enough to jump in! If you’re in this demographic, I’d definitely consider this approach.