All The Questions You Should Ask On A Third Date If You Want To Get Closer To Someone

You've probably seen that viral story about the 36 questions to ask on a first date to fall in love. Call me a skeptic, but I don't believe that really works. But I do believe that asking certain questions on a third date can bring you way closer to someone.

"The third date is crucial, as you’ve already made it through the basic getting-to-know you formalities and passed each others' deal-breaker questions, so you can now get a little more 'real' together," says Emily Holmes Hahn, founder of the matchmaking company LastFirst. "This is right time to kick back and relax with your date, and let your true colors shine."

On a first date and maybe even a second date, you might be nervous. You might have ironed your shirt twice, or caked on tons of makeup when you're normally just a mascara kind of girl, or steered clear of anything too personal, lest you scare your date off. You might have also played games, like not texting them back right away or pretending to not be available on certain nights — and it's time to cut that out, too.

At some point, if you're going to be vulnerable and intimate with someone, you gotta be you. Real, raw you. Holmes Hahn says the the third date is the moment you should drop the protective armor, quit playing games, and ask deep, thought-provoking questions that help you figure out if this person could be your person.

Holmes Hahn created a list of soul-searching questions for you to ask below, but just remember, this isn't a job interview. Don't print this out, highlight your favorites, and bring it to the bar — unless you're naturally the kind of person who's always Girl-Scout-prepared in every situation and that's how you roll... in which case, roll on!

Questions About Their Past Relationships

Did you just recoil? Some people shy away from talking about exes, but Holmes Hahn says this is the perfect occasion to bring it up. Since you're not in that deep with bae just yet, you're probably not so emotionally invested that having the ex conversation will make you jealous. You'll be able to listen more objectively to what they say.

You shouldn't conduct an FBI-level investigation about what went wrong with every previous relationship, but it's totally kosher to ask general questions about this person's feelings about love.

Consider asking:

  • Have you ever been in love?
  • Have you ever been heartbroken?
  • When was the time you felt most vulnerable?
  • How long was your longest relationship?
  • What kind of relationship are you looking for?

Questions About Their Goals

If you're the kind of girl who thrives on the energy of city life, you need to know if the person sitting across from you plans to take over their grandparents' farm.

Consider asking:

  • Where do you hope to be in three years?
  • What's your biggest goal in life?
  • If you could change one thing about your life, what would it be and why?

Questions About Their Family And Friends

This is the kind of thing you might not immediately wonder about when you first start dating. But if you're looking for a serious relationship... it's eventually gotta come up. They didn't become who they are in a vacuum — they're influenced by their loved ones, and you can always learn a lot from how someone talks about these relationships.

Consider asking:

  • What was growing up like for you?
  • Are you close with your parents?
  • Which parent are you closer to and why?
  • Who are your friends?

The purpose of a third date isn't to grill someone on their entire life story. But by the time you part ways (and seal it with a kiss! Holmes Hahn recommends you start connecting physically on this date, if you haven't already), you should have a clearer idea of what this person's life is like — and whether or not you want them to be a part of yours.

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