Guess Less to Connect More

Jordana del Feld
6 min readApr 2, 2024


Have you ever guessed yourself into freaking out?

See if any of these scenarios look familiar:

Your new Tinder hasn’t texted back and it’s been three hours. Is it over? Are they busy arranging a limo to pick you up and take you to that club nobody can get into? Are they trapped under something heavy? What does it mean?

Your wife said she was going to the laundromat and now it’s midnight. Is she having an affair? Is she folding her delicates? Is she dead? What does it mean?

Your boyfriend said he wants to be “monogamish.” Does that mean he wants to get married and is overwhelmed by his feelings for you? Does that mean he’s seeing someone else? Does that mean he’s bored with you? What does it mean?

“What does it mean” is a question we love to torture ourselves with, especially in intimate relationships. Any human choice has an infinite number of possible motivations. And guessing the back-story behind someone’s behavior is a favourite human pastime.

It’s also an instant road to anxiety.

There’s plenty of opportunities for anxiety in any intimate relationship. You don’t have to invent more. Instead, practice giving yourself the gift of calm. Here’s how.

First: Pause.

Building new habits begins with noticing old habits. We can be so used to reacting emotionally to triggers that we might not even notice we’re doing it at first. So this is the first step. Can you notice when you want to start guessing?

And then can you pause? Take a moment. Breathe. Make a note of what you notice happening. Notice how you’re feeling: stressed, worried, anxious,scared, overwhelmed? Take stock. Pause. This might have been a chance for Earlier You to spend the rest of the weekend in a tailspin, calling everyone so you could obsess together for hours, or clamming up in silent panic. But you don’t have to do that any more. Present You is building up healthy tools to take care of yourself. Present You can make healthy new choices.

You might have built up a guessing habit over many years, so it may be a strongly-reinforced reaction to stimuli. It will take some practice to shift. Fortunately, Present You has the rest of your life to build this practice. You can do it.

Remember: notice when the urge to guess arises, pause, and choose constructive behaviors, instead of letting destructive ones choose you. React less. Respond more.

Next: Map.

“Here there be dragons,” old map-makers wrote when they didn’t know what went where. They assumed something was in that corner, but it was unknown, unfamiliar, and therefore scary. There might be golden pomegranates over there, but the map-makers felt safer hiding in fear. Assuming it was dangerous territory. Warning people away. Danger: you might get eaten. For it’s often easier to face a scary answer than to sit with an unfamiliar question.

This is often what we do when we start guessing. We don’t know what’s there, so we tell ourselves it’s dragons. And while there’s a nonzero possibility of dragons, they’re just one of many possibilities. To state the dragons as a fact is wrong.

Better to use the other label those map-makers used. Terra Incognita. “Unknown Territory.” Also “unexplored territory.” For that is true. Over here, on the land under your own feet, you know what’s going on. You’re texting, you’re scrolling Google Maps, you’re calling Tiffany’s to see if someone has set up a bridal registry. Your territory is known to you. But over there, that’s the other person’s territory. You do not know what’s going on.

When you don’t know what’s going on, point this out to yourself. Then stop there. Your guessing self might want to take that as the jumping-off point for a monologue. But now that you’re taking better care of yourself, you’re going to put periods at the ends of those sentences.

“I asked him if he wanted to and he didn’t answer. I don’t know why. [Period.]”

“She’s certainly been spending an amazing amount of time with them lately. I don’t know why. [Period.]”

“I was hoping they would say they wanted to see me again, and they didn’t, and I was hoping for either a real kiss or no kiss at all so at least I could have some clarity, and they gave me this weird half-kiss sort of on my cheek and sort of not, plus I don’t know whether that person with them was their friend or something more. I don’t know what all that means. [Period.]”

Living in a world with other people in it means living in a world of mystery. You might never fully understand what other people are doing, because often they don’t fully understand it either. But giving yourself over to guessing can hijack your time, your energy, and your heart. These are your most precious resources. Don’t give them away.

By noting what you don’t know and cutting the thread there, you’re giving yourself back your time. You’re giving yourself back your energy. And you’re giving yourself back your heart.

This allows you breathing room. You can’t be a healthy part of any relationship if you’re guessing the life out of yourself. But once you can breathe again, ask yourself if you want to discuss the matter with the other person. Is this a worthy investment of your precious time, energy, and heart?

The power of choice, and the freedom to choose power, is yours.

Talk with Them

If you decide you want to discuss someone’s behaviour with them, check your motivation first. If you want to accuse, to wound, or to punish, wait for some other time, when you’re feeling calmer. But if you want to understand the other person better, go forth. You want to understand them. And you want them to understand you. Remembering this will give you patience and clarity.

If you engage this person in a conversation, let them know the topic up front. The calmer your tone, the better. “Hey, happy Tuesday, I hope you’re doing well. I’d like to discuss something you said last week. I’m curious about what you meant by ‘monogamish.’”

Tell them how you feel. Use “I” statements. Instead of, “you’re a heartless boor,” say, “I felt sad when you told me that.”

Then tell them the story you have attached to the situation. No matter how obvious the story is in your head, the person is not inside your head. They do not know your story. And you get extra points for labelling the story as a story. For instance, “the story I’m telling myself about your request is that you are bored with me and want to move on to someone younger and prettier while still coming home to me while I cook for you and clean for you.”

Then take a breath or two. Revisit your goal: you want to understand their viewpoint. “Thank you for listening to my feelings and to the story I’m telling myself. Please help me understand your situation better. What’s your story?”

You could let them know that you appreciate them meeting you like this. And remember that by seeking to understand, you are helping both of you. Clarity is an essential foundation for a healthy relationship. Just like trust and respect, which are two other essential foundations that you are reinforcing by choosing to have this conversation.

By choosing to guess less and pause more, and by choosing to react less and to respond with more equanimity and clearer communication, you are giving your relationship its best possible chance.

By taking care of yourself, you are taking care of both of you.

Good luck!

Jordana is a psychotherapist accepting new California-based clients through the Center for Mindful Psychotherapy.