Is Your Dating Rulebook Getting in the Way?

Dating already comes with enough uncertainty, yet many people enter it carrying an entire collection of rules: never text first, do not respond too quickly, make them pursue you, and, of course, never respond to “WYD?”

Before long, dating starts to feel less like getting to know someone and more like a game where neither person has been given the instructions.

To be fair, dating rules usually do not come from nowhere. They are often created after disappointment, inconsistency, rejection, or one too many conversations that went absolutely nowhere. Psychologically, rules can help reduce anxiety by giving us a sense of predictability and control. The problem is that relationships—and people—are not always predictable.

For many women, receiving a “WYD?” text is immediately irritating. It can feel lazy, vague, and painfully low effort, especially when it comes from someone who regularly checks in but never makes an actual plan. Sometimes “WYD?” really does mean, “I’m bored. Entertain me.”

But it could also be an awkward attempt to ask, “Are you available?” or “Would you like to spend time together?”

The person may be interested but uncertain about whether that interest is mutual. Some people are naturally direct, while others are shy, cautious, awkward, or afraid of rejection. A person can be genuinely interested and still send a terrible text.

Instead of immediately deciding what the message means, you could respond, “Not much. Are you asking because you want to hang out?” That is not chasing—it is clarifying. If the person responds by making a plan, you have your answer. If they continue being vague, you also have your answer.

This is where it helps to understand the difference between a rule and a standard. A rule says, “I never text first.”

A standard says, “I want communication to feel mutual.” A rule says, “I never respond to ‘WYD?’” A standard says, “I want someone who communicates clearly and follows through.” A rule says, “They must plan every date.” A standard says, “I want someone who demonstrates initiative.”

Rules tend to focus on isolated moments, while standards allow us to evaluate patterns. One awkward message may not tell you much. Weeks of vague texts, last-minute invitations, and no follow-through tell you quite a bit.

Our brains naturally try to fill in missing information, particularly when past experiences have taught us to expect disappointment. We may engage in “mind reading,” a common cognitive distortion in which we assume we know what another person is thinking or intending without asking. We may also overgeneralize, believing that because several people used “WYD?” without making plans, everyone who sends it must have the same intention.

Past experiences matter, but they do not always predict the intentions of the person currently texting you. Sometimes curiosity is more helpful than assumption. You can ask, “What did you have in mind?” “Are you trying to see me?” or even, “I’m free Friday. Would you like to do something?”

Direct communication may feel vulnerable, but it can save you from spending an unnecessary amount of time analyzing a three-letter text with the group chat.

Loosening a dating rule does not mean lowering your standards. You can give someone an opportunity to clarify without giving them unlimited opportunities to waste your time. The larger questions are whether the effort feels mutual, whether their actions match their words, and whether the two of you can communicate without playing games.

Dating requires discernment, but it also requires openness. Keep the standards that protect your emotional well-being. Question the rules that prevent you from being honest, curious, and fully yourself.

And the next time someone texts “WYD?” you do not have to write a dissertation. You can simply ask, “Why—are you trying to see me?”