A 90-Day Dating Strategy

The idea borrows from a familiar business framework: get clear on what you want, establish your boundaries, set a target and don’t rely on one channel to deliver the result.

That starts with knowing what you’re looking for.

Kind, funny and ambitious are on the list, although preferably someone “not too obsessed with work, like I am.”

There are boundaries too.

No more three-week text conversations that never turn into an actual date. No more automatically falling back on “I’m too busy.” And no accepting someone disappearing for weeks only to casually pop back up again.

“If I wouldn’t accept a client ghosting me for a month and then reappearing like nothing happened, I’m not accepting it from a man either.”

It’s a funny comparison, but there’s something useful behind it. The standards and boundaries that seem obvious in business can become surprisingly flexible in other areas of life.

Then there’s the question of where these dates are actually going to come from.

Dating apps are described as “the digital lead gen of the dating world”, but they’re only one part of the plan.

Pickleball or paddleball could provide a more natural social environment. Hiking groups are another option. Trivia nights make the list, although there’s some concern the crowd could skew younger.

“They might bring their dad along or granddad along.”

Cooking classes could work too. There’s a shared activity, built-in conversation and a little forced teamwork. And if nothing romantic comes from it, at least there’s a decent meal at the end.

The point is to try different avenues rather than waiting for the right person to magically appear.

“You can’t sit at home waiting for the perfect person to fall through your roof. Just like you can’t sit in your office waiting for leads to fall into your lap.”

Test, Learn and See What Happens

Just like any 90-day plan, the experiment doesn’t stop once the activity begins.

The idea is to actually look at what happens.

Did the dating apps create genuine conversations or just crickets? Did pickleball lead to meeting someone interesting or simply provide a good workout? Did trivia night have a great atmosphere but lead nowhere afterwards?

If something clearly isn’t working after a few weeks, try something else. If one avenue seems promising, lean into it.

“Data doesn’t lie, and neither does a string of bad dates.”

Of course, dating isn’t a business and finding the right person isn’t something that can be guaranteed by hitting a KPI.

That’s partly what makes the experiment so entertaining.

But underneath the dating stories and business analogies is a bigger question: how much attention do we give to the areas of our lives that matter to us?

We can spend hours planning business goals, reviewing results, building strategies and deciding what comes next, while other parts of life are left on autopilot.

Sometimes, making a change simply means being more intentional, putting yourself in situations where something can actually happen and being willing to adjust along the way.

For the next 90 days, the KPI remains simple: one date a week.

And because it’s now been said publicly in the latest episode, there’s a little extra accountability too.

“Wish me luck. I’ll keep you posted. God help me.”