How to Make Every Date Worthwhile

Most online daters have a general idea of the qualities they’re seeking in a boyfriend or girlfriend—smart, funny, athletic, etc. But couples therapist Peter Pearson says the most important factor is often overlooked: your date’s values. Pearson explains that while daters often place a lot of importance on physical attraction and common interests, shared values are what enable relationships to endure.

“Ultimately it’s our value system that is going to set the trajectory of how we get along or not,” says Pearson, whom I discovered through a Tech Insider post on dating.

Our values, he explains, drive our behavior. They determine how much we spend on houses and cars, and how much we save. They determine whether we work long hours to secure a better future, or whether we devote our weekends to enjoying the present with friends and family. They determine whether we travel widely or stay close to home.

This is usually information we glean over time. “You can’t sit down on a first, second or third date and say ‘Tell me about your value system,’” says Pearson.

But the more you date, the more adept you can become at learning the deeper truths about the person you’re splitting that plate of calamari with. A few suggestions:

1) Ask open-ended questions. “Why did you decide to move to San Diego?” “Have you always wanted to be a lawyer?” “Do you have any vacations that you’re looking forward to?” Your questions should require more than a one word answer, but you don’t want to sound like a job interviewer—no “Where do you see yourself in five years?” or “What’s your worst quality?” You also don’t want to sound like a therapist or self-help guru, so skip the canned questions about which historical figure they’d like to have dinner with. (Do you really want to hear them go on about breaking bread with Einstein?)

“Ask questions in a curious, interested, friendly way, so the person doesn’t feel like they are under a bare lightbulb,” says Pearson.

2) Listen to their answers. This sounds obvious, but many people are more focused on what they’re going to say next than on what their companion is saying now. This is not only rude, it’s also is a missed opportunity: Your date’s story about her career change or cross country move will be packed with clues about who she is and what matters to her most. Non-verbal cues also tell a lot. Does your date’s energy rise or fall when talking about his family, his job, his crossfit workout?

3) Ask for details. If your date tells you her favorite movie is The Big Short, ask what she loved about it. Another useful phrase: “Tell me more about that.” Anytime a date indicates he’s talking about something that matters to him deeply—“So that was a big deal to me.” “That’s when I knew it was over”—gently ask him to say more. Again, you’re not interrogating, just showing interest in what he has to say.

Learning to ask questions that are engaged but not intrusive is a skill, one that will serve you well outside the dating realm. If you begin each date with the goal of getting to know another person, rather than evaluating a possible future spouse, you’ll never again have to worry that a particular date was a “waste of time.”

Taking a “fact-finding” approach makes dating both less stressful and more fun. With each date, you’ll gain a deeper understanding of what you’re looking for in a partner, and you’ll probably make a better impression.

After all, when you ask people to talk about themselves, you’ve usually hit on their favorite subject.

its not you sara eckel

Sara Eckel is a personal coach and the author of It’s Not You: 27 (Wrong) Reasons You’re Single. You can get a free bonus chapter of her book at You can also find her on Twitter and Facebook. Ask her any questions here.


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