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4 First Date Questions To Ask So Things Don’t Get Awkward

4 First Date Questions To Ask So Things Don’t Get Awkward

BY Zack Drisko

4 First Date Questions To Ask So Things Don’t Get Awkward

First dates can get f*cking awkward. Sorry, but that’s just life.

It’s not a reflection on you. It’s not necessarily a reflection on the relationship. People can have horribly awkward first dates and end up spending the rest of their lives together.

On the flip side, people can have a great first date and never see each other again.

Bottom line is, when you put two people together who don’t know each other very well, then you get a certain kind of awkward tension that can kill a conversation.

That’s why today, we’re gonna talk about how to drive a conversation forward. The best way is with great questions that create a clear focus. It keeps the conversation fresh and also helps you get to know each other.

Next time you find yourself with nothing to say, bust out one of these first date questions and keep that conversation moving:

“What’s your favorite movie of all-time?”

The other versions of this question are, “What kind of music do you like?” and, “What’s your favorite thing on TV right now?” and, “What was the last good book you read?”

These are some of the best first date questions to break out early on in the date for a number of reasons:

1. No one’s getting offended or weirded out about that shit.

2. It’s a great way to gauge someone’s tastes (she likes ’80s slashers) or a lack of taste (she doesn’t like movies that much).

3. One of these variations is bound to get her talking about something she likes.

Re-read number three. Therein lies the first key of having a successful first date: getting her talking about things she likes. Once you’ve achieved that objective, you’re then looking for places where it overlaps with shit that you also like.

You see, people too often make on of two mistakes:

1. Get her talking about stuff she likes that is boring to you.

2. Talking about stuff you like that she thinks is boring AF

By opening up the conversation with some searching questions, you can find a middle ground. If you think her favorite movie sucks, move on to the books or TV or whatever.

Find something you also like — or can talk intelligently about for more than three minutes — and give it a try.


“What’s your family like?”

Similar to the movies question — except this one is a little more personal. Here’s another way to get her talking about something she knows well, and it’ll tell you a lot about her.

Does she like or family or not? That answer can tell you a lot about her outlook on life, her maturity, or how batshit her family is. All good things to know.

Plus, often times, telling someone about something that feels like “home” is comforting. It can put her at ease. Plus, you have a family (presumably), so you can probably relate to some of her stories.

Related: 3 Steps That Transform A “Cold” Girl Into Your Loving, Loyal Girlfriend

If you’re really shitty at making conversation, you could even have a few jokes or observations about your own family preloaded and ready to go.


“What’s the one thing you need to accomplish in life?”

Most motivated people love talking about their goals and their dreams. This question is a great way of getting a sense of the type of person she is and wants to be.

This is one of those first date questions that you can’t just open right up with. You need to develop a certain rapport that leads to this point.

Pay close attention to her answer. Is she ambitious? Selfless? Unsure of what to say and giving you a BS answer?

Take stock of not only her answer but the answer behind the answer. While that sounds like BS, here’s what I mean: If her goal is to start her own business, don’t be a weirdo, but keep looking for the reason behind it.

Is it because she ultimately wants to be free to do her own thing? If so, that’s her core motivator: the need for freedom.

You might be able to connect with her about that need for freedom and possibly even share your own vision, connecting in a much deeper way than discovering that you both kinda liked Westworld.


“What’s something you’ve always wanted to try?”

Now, we’re trying to get past all the bullshit and planting the seed for future adventures together.

Perhaps her answer is something doable, like playing guitar — something you know how to do. That’s a slam dunk because you could offer to teach her sometime, like as a second date.

Or, perhaps it’s something a little crazier like skydiving. You might want to save that one for later.

Either way, getting her talking about things she’s passionate about and things that she wants out of life is exciting for both of you.

Remember, focus creates emotion. If you spent the whole conversation asking her about shit that she hated, that largely will color her experience.

But, if you focus the conversation on exciting, motivating, passionate things, then there’s a much greater chance that both of you experience those emotions.

It doesn’t guarantee a second date or even that you’ll like each other, but it certainly gives you your best shot.


Falling in love isn’t some magical process. All love stories follow a similar script. We’ve deconstructed it for you so you can take the guesswork out of dating with the Girlfriend Activation System.

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Zack Drisko

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Raised by a police officer and a U.S. Marine, Zack Drisko was taught the ways of the world and hammered on the anvil of life until he became a decent human being. Learn more about him at his website www.zackdrisko.com.

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  • Damien Villano

    I always liked asking what was their last vacation.

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