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The 5 Best First Date Conversation Starters To Help You Actually Get To Know Someone

Striking up conversation with a perfect stranger while having not-so-secret hope that they end up being the love of your life is sometimes awkward.

It's difficult to strike a balance of genuine conversation while still fishing for specific intel on how compatible you are, and it leaves a lot of us with a rolodex of obvious, cliché questions.

And a general rule of thumb: If you're feeling bored with your own conversation, chances are your date is, too.

Luckily, there are a few easy ways to switch up the standard first date flow. By pushing past the obvious questions you think are “safe,” you get the chance to connect a little quicker and deeper than the average first date meet up.

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Below are some hot tips and tweaks for your standard conversation topics to help you get to know one another better.

Instead of “What did you major in in college?” try “Why did you pick your major in college?”

Here's a good rule to follow: If the answer to your question requires a noun, you likely aren't going to get too much info from a person.

Asking a “why” question gives your date an opportunity to explain their preferences and a chance to get to know what motivates them, turns their crank and peaks their interest.


Instead of “Where are you from?” try “Where would you love to live one day?”

Everyone has a past, and no one has control over where they're born and raised.

Sure, you might discover some similarities and learning a person's origin might explain a few things about his/her personality, but asking someone where they want to be in the future gives you insight into their hopes, dreams and passions.

It also may tell you whether or not you guys do have a future together, depending on if the life they see for themselves lines up with the life you see for yourself!


Instead of “What do you do for fun?” try “What's your opinion on [Insert Specific Activity You Love To Do Here]?”

Pick something YOU love doing, and see where they stand on it.

On one page, this might help define how compatible you are, and two, it will give you some behind-the-scenes intel on how they feel about the world and more specifically, their opinions on something you hold dear.

For example, if you find meditating invaluable and they think it's a hoax, you bet your bottom dollar there will be more discrepancies that pop up like that.

Likewise, if they live or die by the NFL season and the idea of spending one second in a stadium near hotdogs makes you want to barf, better call it with the bar tab.

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Instead of “What kind of things do you find funny?” try “When was the last time you laughed so hard you cried?”

I LOVE THIS GAME. I play it with potential lovers and strangers alike. Asking this specific question accomplishes SO much.

First, you get to hear hilarious stories, which is so fun. Second, it instantly brings positivity and lightness to the conversation, cracking any first date jitters and successfully putting everyone in a relaxed mood.

Bonus, you find out more about where and how they see humor in life. Win, win, WIN.


Instead of “Where do you see yourself in 5 years?” try “If you could do anything, what would it be?”

We all have the obligatory Plan B. Sure, everyone would LIKE to have their own Vegas show like Britney Spears, but I probably see myself further advanced in my career, and maybe married with a kid.

Out of those two responses, which is more interesting to you?

Bingo. Britney Spears. Every time.

Asking someone about their hopes and dreams helps you go a little further into their world and teaches you about the kinds of values they hold close to them on life in general.

FYI: All of the questions above are totally fair game, have zero creep factor and make you a more interesting conversationalist in return.

Happy hunting! Don't order the spaghetti.

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Jamie LeeLo

Editor

Jamie LeeLo is a comedian, writer & bull dog enthusiast. She hosts her own talk show, Brunch Night!, currently performing at Caroline's on Broadway. She spends most of her time hanging out on the street waiting for ice cream and taco trucks ...
Jamie LeeLo is a comedian, writer & bull dog enthusiast. She hosts her own talk show, Brunch Night!, currently performing at Caroline's on Broadway. She spends most of her time hanging out on the street waiting for ice cream and taco trucks ...

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