Getting Oriented in Dating

Estimated reading time: 6 minutes


January tends to invite a refresh or a restart — often in the form of big questions:

What do I want?
Where is this going?
Should I be doing something differently?

Those questions aren’t bad, per se, but depending on your situation, they can be premature.

Before you decide where to go, it helps to know where you are.

By that, I mean noticing what’s happening without immediately trying to improve it, optimize it, or explain it away.

In dating, this kind of reflection can be clarifying.

Movement vs. Progress

A lot of dating stress comes from confusing movement with progress.

You can be busy — updating your profile, matching, texting, going on dates — and still feel stuck. You can also be moving slowly and learning a lot.

Paying attention to your starting point helps you tell the difference.

Emotional signals matter here, especially being able to tell calm from boredom, or anxiety from excitement. I’ve written about emotional clarity before, if that’s useful context.

Questions like “What should I be doing?” tend to be most useful only after you understand where you are and what you’re actually trying to move toward.

This connects closely to something I wrote about last year in Go Slow to Go Fast.

What Paying Attention Looks Like in Practice

This kind of awareness may not be obvious.

In dating, it often shows up as fairly ordinary observations:

  • Certain conversations leave you energized or drained

  • You feel relief when a date ends or when it continues

  • You’re spending more time explaining what something means than noticing how it feels

  • You feel calm afterward — as distinct from feeling bored, anxious, or keyed up — even if you’re not especially excited

None of these observations require immediate action. But they are informative.

They tell you something about your baseline — your energy, your pace, your level of interest, and your tolerance for uncertainty.

The Urge to Act Quickly

Many people move past this step too quickly because uncertainty is uncomfortable.

When something feels unclear, the impulse is often to:

  • try harder

  • give it more time than feels right

  • talk it through repeatedly (with yourself or others)

  • make a decision simply to reduce ambiguity

Taking a bit more time to notice what’s happening can be useful — at least long enough to see whether patterns are forming:

  • Confusion that resolves quickly is different from confusion that reoccurs.

  • Nerves that settle are different from tension that persists.

  • Curiosity that grows is different from curiosity you have to convince yourself into.

Paying attention helps you tell those apart.

Take Baby Steps

I’m a big fan of the movie What About Bob?. There’s a scene where the psychiatrist tells Bob to take “baby steps,” and Bob takes that advice literally. It’s a silly joke, but the premise is sound. In dating, small, deliberate adjustments are usually more useful than dramatic resets.

Examples of “baby steps”:

  • slowing the pace

  • shortening dates

  • seeing someone one more time without overthinking it

  • taking a break without labeling it

  • paying attention to how you feel after instead of during

Start Here

If you’re not sure where to begin, start by asking yourself:

  • What’s draining your energy right now?

  • What’s giving you energy?

  • Where are you explaining things more than experiencing them?

From there, the next step usually becomes clearer.

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Understanding How to Bring It Up