How to Plan a Date

When men plan dates, they often make a few basic mistakes. They plan dates that are traditional dating activities – dinner and a movie, for instance – but are not conducive to conversation or building rapport. Many men seem to believe that if they simply show up and pay for everything they are doing everything right. They overreach, they overspend, and they overcommit. I knew a guy in college, for example, that invited a girl on a date that included: (1) coffee, (2) ice skating, (3) dinner, (4) a Timberwolves game, followed by (5) dessert. That’s an eight-hour commitment for a first date. That sounds exhausting.

(What might be worse, though, is the sort of guy who doesn’t really plan anything at all. Why ask someone on a date if you can’t be bothered to plan one?)

Back when my buddy Wilmo was dating his future wife Jessica, he and I had a conversation about this. We realized that the men who like to plan and be in control need to resist that urge. We realized that one of the most important components of date planning is eliminating the obstacles that help people connect with one another. A drawn out, epic — albeit thoughtful — date might be adding obstacles of pressure, stress, and apprehension. Rather than trying to plan comprehensively, they should plan for modularity. This is when we stumbled upon a concept that’s both so basic and so useful that I incorporate it into almost every social outing that I plan, romantic or not. We called it a circuit.

Here’s how a circuit works. Unlike the above example, where you explain the entirety of the date in advance, you simply pitch a “focal activity.” A focal activity is the primary selling point of the night. If you want to go to a concert, that’s your focal activity. If you want to go ice skating, that’s your focal activity. It can even be something as simple as getting ice cream. From there, identify at least two supplemental activities that are 1) organically related to the focal activity in some way and 2) within walking distance. For example, let’s say you invite your date to go ice skating. Plan to extend the date to the nearest coffee shop, but don’t announce that intention. If you finish an hour or so of skating and want to continue the date, suggest you warm up with some coffee or hot chocolate. After that, it would make sense to go somewhere casual and get a bite to eat. (It’s best to be, well, smooth about that. It’s a suggestion, not a rigid proclamation of “Now let us do the next thing I want to do.”)


There are many advantages to this approach. If you are not having a good time – or there’s no real rapport or connection – you can finish up with the focal activity and end the date with full diplomacy. If you’ve already planned an additional activity, it’s awkward and impolite to cancel those plans when you are already out on the date. Secondly, a circuit gives the date an element of spontaneity and projects both adaptability and resourcefulness. On top of all of that, it allows you to spend as much (or as little) time together as you both feel like spending. I had one such date last thirteen hours: it started with coffee, moved to a playground, extended to guitar shopping at Willie’s, transitioned to Pad Thai (we ordered the pad thai), and included at least three more activities after that.

The circuit concept is adaptable to virtually any type of date you might plan. It helps eliminate some common dating pitfalls is both naturally spontaneous and allows you to hedge your bets. Think of it like adding salt to a stew: you can always add more, but you cannot take out what you’ve already put in. Or think of it through this lens. Dwight D. Eisenhower once said, “In preparing for battle, I have always found that plans are useless, but planning is indispensable.” A date like the one my college friend planned eliminates options, whereas circuits enable them.


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