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Three tips for great first dates

First dates are notoriously a crapshoot, even when you've been chatting for a bit on an app. "Am I going to be bored? Or feel trapped? Are they going to like me?"


First dates have the potential to be truly fun - getting to know someone can be enriching, whether we end up going for another date or not. But often, we're approaching first dates all wrong.


We're either hoping they like us, focused on the impression we're making and not on the person we're dating, or we're testing the other person to see if they're the perfect date. (This is not the same as getting to know someone. This is running auditions for "soulmate.")


Whether you're a nervous first dater or just burned out on endless first dates, these three tips will create more fun and connection for you and your date, and you'll leave the date with a way better understanding of whether you're a good match!


number one: skip dinner and drinks

Why? Because it's so. Boring. Snooze. Opt for something where you're moving around, won't be interrupted too often, and can still talk to each other. Going for a walk or hitting a museum exhibit are great ideas. Why moving around? First, it provides a little relief from the sitting-across-from-each-other dynamic that can feel intimidating and/or boring. Second, movement is regulating, so if you're nervous, it can relieve some of the tension of stillness. Lastly, when you're moving, the scenery changes and you can use it to facilitate interesting conversation.


Choose something where you're mobile but not going to be interrupted, like at a bowling alley. Games are a fantastic way to get to know someone, but for a first date, focus on talking to each other. That's a better gauge for whether a second date should happen.


Quick note: drinking alcohol may lower inhibitions, and therefore help you feel more relaxed if you're nervous, but you'll be a better judge of whether you want a second date if you skip 'em.


number two: ask more interesting questions

"And meeting someone new? Ugh, all the nodding, and smiling, and sibling listing?"-Liz Lemon, 30 Rock

How many times can you possibly find it interesting to describe what you do, what you do for fun, and where you're originally from? Your dates are just as bored being asked those questions, so let's get outside of the box.


Here's the golden rule: ask open-ended questions about what they are interested in.


Likely, you met on an app and already have an idea of what their hobbies are. Start there! But rather than asking, "when did you start surfing?" which is super predictable, change it up!


  • What do you like about (where you live/your hobby)?

  • What's your favorite memory of ________ and why?

  • Why _______ instead of, say, _______?


The idea behind these questions is not to gather objective facts about them, but to build an understanding of their values and how they think. This not only allows you to check in that your values are compatible with theirs (not matchy-matchy, but compatible), it also lets them shine!


If you're on a date like the museum exhibit idea, you can also ask questions about their immediate experience:


  • What do you like/not like about this piece? (depending on their reaction)

  • What is resonating with you here?


Remember, the goal is to understand their inner experience, to see it through their eyes for a short time, not to gauge their knowledge of art or art history. (Because, seriously, who f*cking cares?)


number three: follow up questions with reflections & Impact

It's easy to let a great response slide into awkward silence, and that usually indicates a missed opportunity to get to know someone. After your date has responded to your interesting question, reflect back to them what you heard.


Your Date:"I love this part of the city - it's so diverse, the restaurants are these fantastic hole-in-the-wall places, all family-owned."

You:"Ah, so a big part of loving this part of the city is it's restaurants, these family-owned hole-in-the-wall places." Reflecting shows that you are listening to your date, you're paying attention to them and interested in them. It also leaves room for them to elaborate on something they want to talk about. This helps you continue to get to know their values. Sharing impact allows your date to see inside your inner world. They may be nervous, too, so giving them clues about how you're responding to what you're hearing can put them at ease. "I feel curious about this, say more!"

"I'm resonating with what you're saying, I feel _______."


This is warm and inviting, it's showing receptiveness and a willingness to share your perspective, too.


what next?

Now what if you're not curious or resonating or finding them interesting? What if they aren't asking anything about you? What if you're noticing that you find their values repulsive or shallow?


That's a good indication that it's not worth pursuing a second date.


It happens! Move on to the next one.


PS - If you want a more in-depth training on how to have excellent first dates, check out my FREE online course: First Date Rehab. Click the button below to check it out!




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