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Proposal Pitfalls

Updated: Jul 2, 2020

I recently had lunch with a friend whom I had counseled and supported through a difficult time involving the end of her marriage a few years ago. “Kelsey” and I caught up over salads and since I knew she had met someone wonderful shortly after I coached her, I was eager to hear how the relationship was progressing.

“Carter tried to propose!” she said with a smile. “Well, sorta kinda.”

“How do you sort of, kind of propose?” I asked.

She told me the story of how he had reached out to her family to make sure that his proposal would be well-received, then planned a romantic dinner to celebrate the anniversary of when they started dating. He had considered every nuance down to the last detail – including where they sat and what drinks they ordered. But he sabotaged himself before he could even get the critical question out.

Carter aborted Mission “Will you Marry Me” when he launched into a “How will we solve thisproblem if it comes up?” and “What will we do if your kids ever do this?” series of questions that rivaled the Spanish Inquisition. Kelsey was overwhelmed and confused. Her romantic dinner had taken an abrupt turn. And Carter’s proposal was completely derailed.

While there is a long list of critical questions I hope every “intended” couple is asking as they inch toward matrimony, it isn’t necessary (or even advisable) to dispense with them all in one sitting. Carter set up his proposal to fail when he tried to iron out every conceivable wrinkle before it even happened. Is it good to be prepared and ask a few “What if’s?” Absolutely? Do you have to map out a comprehensive plan that anticipates every problem you had in your LAST relationship plus all the new ones you expect will crop up?


It’s easy to see why Carter’s proposal flat-lined because we have an outsider perspective. Bless his little heart, he was trying to do his “Due Diligence” before making it official! But there’s an important “learning opportunity” here:

If you’re advancing toward commitment in some form (whether it be moving in, a common law arrangement, or a full-blown church wedding), it IS a wise idea to have some premarital or pre-cohab coaching. I do that. And if you’re already going to marriage prep workshops or doing marriage counseling with a pastor or therapist, working with a dating coach as you deepen your relationship is the perfect complement to that activity. (Don’t worry, they aren’t at odds; they’re different yet equally valuable!) Once you’ve gone down your checklist of contingencies and are feeling more prepared, you’ll be free to plan a romantic proposal that you’ll remember for the rest of your lives!

If you’d like to explore this with me, I want to hear from you!

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