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6 clever ways to get to really know someone on a first date

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Talking about the weather probably buys you about 30 seconds, and then you flounder for something else to fill the awkward silent gap between you. It’s enough to get the pulse racing even in a wind chill of -12 degrees.

First dates are awkward, and conversations can drag or hit a wall. But you can be the ice breaker that hauls your evening into more tropical waters.

These are six clever ways to have sparkling conversation on your next first date. They can also help you determine whether the two of you have a connection–and where your night might be headed.

One thing you’ll notice is that many of these conversation starters are questions. Seems obvious but it’s important to remember that asking questions is better than droning on about yourself. In fact, asking questions could be considered a key overarching strategy for first-date success.

What do you like to do outside of work?

The old “what do you do?” question is so obvious it doesn’t warrant a bullet point on a list of clever approaches. But this alternate version flips the original on its head, providing a refreshing contrast and helping pivot the conversation away from tech stocks and TPS reports.

The question is deceptively wide-ranging, giving your date an opportunity to discuss family, hobbies, personal interests, favorite Tik-Tok accounts, or pretty much anything else they want to tell you about themselves. In other words, it’s a probing question that avoids being invasive.

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Is there anything on this menu that you won’t eat?

Another clever twist on the typical chit-chat. With so many different diets out there — gluten-free, vegetarian, pescatarian, flexitarian, vegan, keto, lower-carb, paleo, Mediterranean — it can be a great conversation starter to find out more about a person’s lifestyle.

Another piece of more general advice: never underestimate people’s desire to talk about themselves. Obviously, this doesn’t apply to everyone, but it’s natural for people to want to share in social situations. There’s nothing wrong with simply encouraging that.

Tell them something you don’t tell most people

It doesn’t need to be a deep, dark secret. But if you think things are going well, drop something into the convo that isn’t always first-date material — and let them know it’s not something you typically share.

It could be something silly like your award-winning doll collection, or it could be something more poignant, like a certain person or issue that’s especially near and dear to your heart.

If your date seems to appreciate the inside glimpse — or, ideally, shares something in return — that’s a strong sign of positive vibes.

How would you plan the perfect vacation?

This question is an invitation for your date to think more deeply than the more common travel questions about top bucket-list destinations and so forth.

What sights or experiences would you most like to see or do while you’re there? Would you center the trip around one place or would you hit multiple destinations? Will you fly first class or rent an RV? What’s the local food or drink you’d most want to try?

You can see that any number of conversational paths can easily open up. Since everyone has their fantasy trip mapped out in their heart of hearts, this question is almost certain to get a robust response every time.

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What was the last book you really got into?

Let’s be honest for a moment: we’re not all big readers.

Asking this question about reading, rather than asking a more daunting question about the most recent book completed or favorite authors, can make the subject more inviting.

And let’s be honest, we don’t always happen to be crazy about the last book we read. Engaging your date instead about the one they were most interested in allows him or her to pick a book they feel passionate about.

Are you an animal person?

The most likely answer here is a clear “yes.” Whether someone has four dogs or just likes to watch ocean documentaries, this will be a conversation that’s easy to enjoy.

After all, it’s almost impossible to be nervous when you’re talking about your favorite animals. This can also be a gentle way to open the door to wider and perhaps more sensitive topics, such as animal cruelty or degradation of the natural environment. Everyone has topics they care about, and animals can stir a lot of strong emotions in people.

These six conversation starters all can help you put your first-day awkwardness behind you. Before you try these out in the field, consider your own answers so you’re prepared with thoughtful responses.

We’ve presented these strategies because they’re provocative without being nosy. The last thing you want to do is try too hard and accidentally step over the bounds of privacy or respectfulness. By the same token, it can give you a leg up to start and maintain the conversation with topics beyond the bland basics. These six strategies provide a Goldilocks solution, just right for making that first impression.

BlissMark provides information regarding health, wellness, and beauty. The information within this article is not intended to be medical advice. Before starting any diet or exercise routine, consult your physician. If you don’t have a primary care physician, the United States Health & Human Services department has a free online tool that can help you locate a clinic in your area. We are not medical professionals, have not verified or vetted any programs, and in no way intend our content to be anything more than informative and inspiring.

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Scott Harris
Scott Harris is a freelance writer based near Washington, DC, with more than a decade of experience covering health…
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