Date ’Em Til You Hate ’Em

How do I know if they’re the one?

As a dating coach and matchmaker, this might be the question I get asked the most—and is part of the reason I wrote my new book, Matchmaker, Matchmaker: Find Me a Love that Lasts.

But, in my opinion, there’s a better question: Do you know for sure that they’re not?

This second question can give you a lot more clarity than the first, and it will make it easier to take the next step: Date ‘em til you hate ‘em.

Just to be clear, I don’t mean that you should literally hate them. Nor am I suggesting that you should force a relationship that isn’t working or drag things out indefinitely. In fact, I mean the exact opposite. Date ‘em til you hate ‘em means that you should keep dating the person, no matter what, until you’re 100% sure this person is not for you and never will be.

I’ve seen too many daters get in their own way, stressing over whether they’ve found “the one” before the relationship has even really begun. They overanalyze every word, every gesture, trying to predict the future instead of actually building something in the present. On the flip side, people stay in relationships well past their expiration dates, hoping that the other person will change. They wait for a sign or a moment of clarity, and end up wasting a lot of precious time.

With Date ‘em til you hate ‘em, the guesswork disappears.

“When You Know, You Know” Is a Cop-Out

People love to say, “When you know, you know.” But what does that really mean? In my view, it’s just another way of saying, “My only job is to recognize my person when they magically show up.” This kind of thinking absolves people of responsibility, excuses them from effort, and tricks them into mistaking physical attraction for real connection.

Imagine you wanted a promotion at work. Would you just sit around and wait for your boss to hand it to you? No way! You’d show up early, take on extra projects, and prove your worth. You wouldn’t rest until that promotion was yours. Why should finding your person be any different?

Love isn’t always something that just happens. It can be cultivated intentionally, like a good habit. This may not sound as exciting as a whirlwind, love-at-first-sight moment, but the results last a whole lot longer. And when you actually put in the time and effort to build a relationship, that’s when “When you know, you know” actually means something—because you will truly know whether or not this is the person for you.

Trust the Science

Dating isn’t about instantly figuring out if a relationship will work. It’s about gathering enough real-life data to make an informed decision. Think of yourself as a scientist running an experiment: first you observe and collect adequate information, then you draw a conclusion.

This is where most people go wrong. Instead of experiencing the relationship as it unfolds, they jump ahead, trying to decide everything based on tiny, often superficial details. This can easily derail a relationship.

I know a woman, for example, who broke it off after the first date, once she learned her date’s astrological sign. If she’d stuck around for a few more dates, she might have learned that he was also caring, loyal and incredibly funny. But she missed out because she didn’t give the Taurus more time.

This is exactly what we want to avoid.

It often takes at least five dates—genuine, intentional dates—to even begin to understand someone. Rushing to a verdict before that is like trying to solve a puzzle with half the pieces missing. Unless it's a hard no, and in that case you can bail out sooner.

If you’re going to date ‘em til you hate ‘em, mentally commit to going out for at least five dates–and use them only to get to know the other person. No dissecting, no strategizing, no “Where is this going?” Just observe, listen, and connect. Get to know them as a human being without the pressure of making a decision.

When in Doubt, Go Out

So what happens at the end of five dates? That’s up to you. If you’re sure they’re not your person, say your goodbyes and move on. But if you don’t have a 100% hard no, it’s not time to end things. Continue going out with them until you reach that 100% no–or surprise yourself by getting to a yes. Clarity will come, but only if you allow yourself to be present and pay attention.

Some people figure things out quickly. Others need more time. The key is to keep dating until you reach that unmistakable certainty: either this is something worth building or this is absolutely not my person.

When you know, you know. And until then—date ’em til you hate ’em.