Milk and Honey Magazine first date questions to ask so you never have an awkward first date again!

40 Questions For a Perfect First Date

M&H Staff

Your brother knows a guy with a cousin that would be perfect for you. You add each other on Facebook, send a couple messages planning to meet, and choose a time and location. Sound familiar?

You leave work a little early to recurl your hair, spray another spritz of perfume, and regloss your lips. You mentally prepare with a little Britney playing on your Pandora, telling yourself it'll be no big deal.

Walking into the dimly-lit restaurant, suddenly feeling this place is way more formal than you remember, you sit in the lounge, order a Kombucha on-tap, and await your fate.

He walks in, tall and handsome as he looked via the web, and you stand, straighten out your skirt, smile a bit too wide, and offer your hand to shake. Laughing a bit, you sputter: "Nice to uhh... nice to meet you!"

Getting ushered to your table overlooking the city lights, you promise yourself to stick to afternoon coffee shops for blind dates in the future, feeling a little underdressed in your summer dress and flip-flops.

As the conversation gets started, you begin to sweat. "What if it gets awkward? What if there's nothing to say? What if the conversation grows dull?"

As the date progresses, your worst fear comes true.

Him: How’s your salad?
You: Good. And yours?
Him: Yeah, really good.

The conversation dims, you haven't even received your main course yet, and you have no clue how to get the important questions answered (faith, family, values).

✳ ✴ ✵ ✶ ✷ ✳ ✴

Have you run into a similar situation? A first date that grew dull too early? Where you were nervous, stumbling for conversation topics? While this may be a sign he's not 'the one,' it could also mean you're both not asking the right questions!

So, without further adieu, we created the M&H First Date Question Guide, to ensure you never run into a dull date again!

Milk and Honey Magazine first date questions to ask so you never have an awkward first date again!


  • What do you do in your free time?
  • Who's your best friend? How'd you meet?
  • What's something you've always wanted to learn?
  • Do you go to church?
  • Are you close with your parents?
  • What's your biggest goal in life?
  • Who is the kindest person you know?
  • What's your favorite thing to do on a Saturday?
  • What's a recent movie you saw and enjoyed?
  • Who are 'your kind of people?'
  • Do you have any pets?
  • What are you most grateful for?
  • What cheesy song do you love?
  • How many siblings do you have?
  • Who's your favorite author?
  • What was your favorite part about high school?
  • Where would you travel if you could go anywhere right now?
  • Turning points in your life?
  • Are you an introvert or extrovert?
  • Favorite sport to watch? Or play?
  • Do you volunteer?
  • What was your family like growing up?
  • What's your silliest fear?
  • What kind of music do you never grow tired of?
  • Happiest year of your life?
  • If you wrote a book, what would it be about?
  • What's something I wouldn't expect about you?
  • What's your go-to funny story?
  • Favorite quote or saying?
  • What city would be the best to live in?
  • What superpower would you love to have?
  • Where do you feel most out of place?
  • What would you do for a career if you didn't need the money?
  • If you could give your younger self advice, what would it be?
  • What's your favorite type of food?
  • What's something you could talk about for hours?
  • Where do you want to retire?
  • Where do you spend the most of your time besides home and work?
  • Do you have any secret talents?
  • What actor would play you in a movie about your life?