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#486 - Even the Dating Coach Has Bad Dates

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Confession: the dating coach had a rough date this past weekend.

I’d love to tell you that more than a decade of coaching midlife singles makes me immune to bad dates. It doesn’t. I’m out here doing the very same thing you are.

How it went

We met for a beer before a casual dinner. Within the first few minutes, I learned three things.

First, my questions were “terrible.” Not in a playful way. I usually got a non-answer, the question turned back on me, or a flat “That was a terrible question. Try again.”

Second, I could use some pointers on connecting with my own grandkids. This came from someone who had never had children, and who was crystal clear on what I should do differently without knowing anything about my family.

Third, there is only one football team worth talking about, and only one city worth visiting. Hers.

I’m not here to judge her. I only saw one evening, and I’m sure there’s more to her story. I’m here to share what I noticed, and what I did with it.

I had an exit. I didn’t take it.

The beer was a perfectly good exit. Did I take it? Nope. I stayed for dinner. Honestly, I was hungry. And I was curious to see where it would go.

Spoiler: more of the same.

But I wasn’t staying because I hoped it would turn around. By the end of that beer, I already knew this wasn’t a match. Dinner wasn’t a rescue mission. It was a meal and a front-row seat.

Are you seeing the patterns?

What struck me most was how fast it all showed up. One dismissive comment, I’d have shrugged off. Could be nerves. One strong opinion about football? I’ve got a few of those myself. But by the time the beer was half gone, I’d heard the same thing three or four different ways.

And I knew. I think most of us do. When people tell me their dating stories, they almost never say, “I had no idea.” It’s usually, “I kind of saw it early, but...”

So, it’s not an intelligence problem. It’s a decision problem.

Dinner with my eyes open

Once I’d made up my mind, the pressure was gone. I wasn’t trying to win her over or hunting for common ground. I was just enjoying a meal, paying attention, and finding the whole thing a little fascinating.

I hear the other version of this story all the time. Someone sees the same pattern, then talks themselves out of it. Maybe I’m being too picky. Maybe they’re just nervous. So they stay out of politeness or hope, drive home drained, and sometimes say yes to a second date they didn’t want.

Same dinner. The only difference is whether you’re sitting there with clarity or with hope.

What I took away

This date reminded me of something I already knew: I want a conversation where both people are curious about each other. Where a question gets a real answer. Where someone can disagree with me without trying to correct me or put me down.

That’s not a high bar. But it’s my bar, and a rough Saturday night made it a lot clearer.

Your turn

Think back to your last date that didn’t go anywhere. Was there an “I kind of saw it early, but...” moment? A comment you brushed off? A question that never got a real answer?

What’s the early sign you keep catching and then talking yourself past? Leave a comment or hit reply. I read every one.

If that “but” keeps winning, it usually means you’re not completely sure what you’re looking for, or you don’t fully trust yourself yet. That’s exactly why I created Finding Extraordinary Love. It walks you through the patterns in your own dating history and helps you build your Must Haves and Deal Breakers, so the next time something shows up early, you’ll recognize it and trust what you’re seeing. Get the workbook here.

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#486 - Even the Dating Coach Has Bad Dates

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