Life, if you think about it, is one long decision marathon. It starts first thing in the morning: hit snooze or be that responsible, on-time person you keep promising to become? Wear the black skirt… or the other black skirt? Eat breakfast or “accidentally” live on coffee again? At the supermarket, there are so many choices — Cheerios or corn flakes, Heinz or Hunt’s, Barilla or Ronzoni, aisle 4 or aisle 7? And of course, whichever line you choose, the other one will always move faster.
Most of these don’t really matter in the grand scheme of things. But every so often, life throws in a decision that does. I had such a decision recently. There was a family emergency while I was away on vacation, and I had to decide whether to cut my trip short. It wasn’t an easy decision to make, because whichever way I leaned, something would be sacrificed, but I am used to making decisions – big and small – so I did not get stuck with indecision.
Decision-making is a muscle. The more you use it, the stronger and more intuitive it becomes. This may or may not be the only muscle getting consistent workouts over here. Just saying. If only choices counted as cardio, we’d all be in incredible shape.
Dating often turns otherwise competent adults into people who can’t decide between “yes,” “no,” or “maybe I should ask three friends and a rav first.” It can feel like one long conveyor belt of choices. Say yes to this name? Go out again? Give it more time? End it now? Open your heart? Protect your heart? And that’s before we get to the real crisis: choosing which shoes to wear to the date.
No wonder singles feel worn out before they even sit down across from someone in a hotel lobby.
Too Many Choices
It’s easy to assume that more options should make dating easier. More résumés should mean more potential, right? But that is not how the human brain works. Too many choices tend to blur our clarity. The more possibilities appear, the harder it becomes to feel secure in any one direction.
What’s supposed to feel like opportunity starts to feel like pressure. You’re trying to be open-minded, but every new choice adds another layer of “What if I’m making a mistake?”
Psychologists call this “decision fatigue.” The more choices you have to make, the more drained and reactive you become. That’s when people either shut down and avoid deciding at all, or default to whatever feels easiest in the moment. Suddenly, every new suggestion feels like your brain saying, “Cannot complete action. Storage full.”
When Fear Pretends to Be Clarity
One of the trickiest parts of decision-making is that fear is an excellent actor. It shows up dressed as logic, carrying spreadsheets, sounding very official. People often think they’re making a clear, reasonable decision when in reality they’re making a fear-based one.
“I just know this isn’t right” may really mean, “I’m scared of where this could go,” or “I’m scared to get hurt again.” Clarity and fear feel very different in the body. Clarity can still feel sad or hard, but it usually feels steadier and more grounded. Fear feels tight, rushed, urgent, like you have to decide right now or something terrible will happen.
Learning to distinguish clarity from fear is a core decision-making skill. A simple question to ask yourself is: “Am I choosing from peace, or from panic?” If the answer is panic, it might be a sign to slow down.
Head, Heart, and Gut: Who’s Driving?
When you’re trying to decide what to do in dating, you usually have three voices chiming in.
- The Head: “Does this make sense on paper?” It cares about logic, background, timing, age, life plans.
- The Heart: “How do I feel when I’m with this person?” It cares about connection, warmth, and emotional safety.
- The Gut: That quieter sense that something fits, or doesn’t, even before you can explain why.
Healthy decisions rarely come from silencing two of these and only listening to one. If you only listen to your head, you might ignore chemistry and emotional needs. If you only listen to your heart, you might minimize big red flags. If you only follow your gut without checking in with the other two, you might move too fast or misread your own anxiety.
Of course, they never speak at the same volume. The heart whispers, the gut murmurs, and the head rents a megaphone.
Sometimes the most helpful thing is to literally sit down and write: “What is my head saying? What is my heart feeling? What is my gut sensing?” Seeing the answers on paper can bring surprising clarity.
Learning to Live with Doubt
Here’s something that doesn’t get said enough: you can be in a good place and still feel doubt.
You can like someone and still have questions.
You can make a solid decision and still wonder if you did the right thing.
Questions and uncertainty are common as things get more serious. Doubt doesn’t always mean “wrong.” Sometimes it just means you’re stepping into something real, and that can be scary.
There’s the kind of doubt that taps you on the shoulder and says, “Something’s off here.” And there is the kind of doubt that shows up when you take a step toward deeper vulnerability or commitment.
Doubt doesn’t always mean “turn back.” Sometimes it means “you’re stretching.”
The Little Choices That Shape Big Outcomes
We tend to focus on the big decisions:
“Do I say yes to this suggestion?”
“Do I keep going?”
“Do I get engaged?”
But it’s the tiny decisions that shape the direction of a connection. Do I choose to open up a little more instead of shutting down, to be curious about the person in front of me instead of comparing them to the imaginary husband or wife in my head, to stay present instead of mentally planning the exit, to say “I had a nice time” instead of waiting for them to go first?
Over time, it’s those small choices that decide whether something stays surface-level or becomes deeper. When you feel overwhelmed by the “big” questions, it can help to ask, “What kind of “small” choice can I make today?”
The Courage to Choose
When you’re stuck on a decision, you can try the “two-scenario check.” Sit somewhere quiet and imagine you’ve already chosen one option. For example, that you’ve decided to keep going with this person. Picture it as if it’s real. Then notice what happens inside your body: do you feel a bit more open or a bit more tight, a sense of ease or a knot in your stomach?
Then do the same with the other option. Imagine you’ve decided to end it, say no, or take a break. Again, imagine it as if it’s already done, and pay attention to how your body responds. You’re not looking for what sounds most logical on paper; you’re paying attention to which option gives your body a calmer, more settled feeling, even if it comes with some sadness. That physical response is often a better guide than another hour of overthinking.
There will always be another angle to pick apart, another person to ask, another scenario to imagine. At some point, it stops being about analyzing every what-if and starts being about trusting yourself. Otherwise, you’ll still be sitting there in 2043, making a pro-and-con list with 900 bullet points.
You can tell yourself, “I made the best decision I could, and I stand behind it.” That doesn’t mean you’ll never feel doubt or fear; it means you won’t let them drag you back into endless replay mode. Trust grows every time you choose, commit to that choice, and let yourself move forward instead of constantly checking if you were “right.”
And if you’re finding that your head, heart, and gut keep talking over each other, or if the same doubts keep circling without landing anywhere, sometimes it helps to think it through with someone outside your own head. That’s kind of my thing.
