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THE 4 BEST TYPES OF FIRST DATE QUESTIONS

A far more measured approach than: "just ask her a bunch of questions; women love speaking about themselves."

1. Questions that invite her to vent

Everyone likes to complain. Plus, it builds rapport, uncovers commonalities, and often creates opportunities to flirt and tease.

Examples:

  • "What's the worst movie you've seen in the past twelve months?"
  • "What's the most annoying assumption people make when they first meet you?"
  • "What's a current fad that you despise?"
  • "What's a terrible pick-up line you've recently heard?"
  • "What's the worst topping you've ever seen on a pizza?"
  • "What's the worst advice someone has given you?"
  • "Which app on your phone annoys you the most?"
  • "What's the worst thing that happened to you today?"
  • "What's the most frustrating traffic situation you've experienced?"
  • "What's the most annoying habit you've encountered in a roommate?"
  • "What's the worst piece of advice you've received about dating?"
  • "What's the most annoying question people ask you repeatedly?"
  • "What's the most frustrating household chore for you?"
  • "What's the most disappointing ending to a TV series or movie?"
  • "What's the most annoying fashion trend you've seen on social media?"

KEEP IN MIND

It’s not for everyone

If she doesn’t like speaking negatively, change your questions. Or at least add some positive questions in to lighten the mood:

  • "What's the worst movie you've seen in the past twelve months, and the best one?"
  • "What's a current fad that you despise and one you secretly love?"
  • "What's your favoUrite television series, and who are your favoUrite and least favoUrite characters?"

Moderation is important

Overdoing these questions makes you sound like a generally negative person.

Keep it light

Only invite complaints about amusing or trivial topics. Avoid deep and serious topics.

Amusing and trivial:

  • ‘What do you find more annoying: people slurping soup or people bumping into you on public transport?’
  • ‘What’s the most embarrassing song that’s been stuck in your head?’ 

Deep and serious:

  • ‘What’s the most traumatic thing you’ve ever experienced?’
  • ‘Who in your life has negatively impacted you the most?’

2. Questions that showcase her pride

People love discussing their achievements, particularly when prompted by others.

  • "What's the most thoughtful gift you've ever given and/or received?"
  • "What was your proudest accomplishment this week?"
  • "What's something you've done as an adult that would make your ten-year-old self proud?"
  • "What's the best thing that's happened to you this month?"
  • "What's the best thing about being your friend?"
  • "What's a skill or talent you've developed over the years that you're proud of?"
  • “What’s something you’re secretly really good at?”

Help her if she needs it

Sometimes, she might struggle to answer or feel hesitant about bragging. In such situations, take the lead and share something about yourself to make her feel more comfortable. For example:

You: "What's your proudest achievement this week?"

Her: “Hmm.. that’s a hard one.”

You: “Want me to go first?”

Her: “Yes please.”

You: "I kept a scammer on the phone for 27 minutes during my lunch break at work."

Beware

Stacking too many of these questions can make it sound like you’re conducting a job interview. Use them sparingly.

3. Questions that entertain and amuse

All women enjoy dates that spark their interest, entertain, and amuse them.

Examples:

  • "Who was your first celebrity crush?"
  • "If you were wrongly accused of a crime and put on death row, what would you order for your last meal?"
  • "What's your greatest yet least useful talent?"
  • "What's your go-to hangover cure?"
  • "What's the wittiest comeback or response you've ever delivered in a conversation?"
  • "How would your best friends describe you in three words?"
  • "What's the weirdest food combination you've ever tried and surprisingly enjoyed?"
  • "If you could be a character in any TV drama, who would it be?"
  • "What’s the worst autocorrect fail you’ve ever witnessed?"
  • "What TV series have you rewatched multiple times?"
  • "If you had a comedy roast, which friends or family members would you invite to roast you?"

4. Questions that inspire thoughtful conversations

Thoughtful questions add depth, build rapport, and make your conversations more interesting.

  • "If you could give everyone on earth one piece of advice, what would it be?"
  • "If humans never had to sleep, what would you do with your extra time?"
  • "What's the most unlikely situation in which you've made a friend?"
  • "What movie or TV series do you turn to when you can't find anything else to watch?"
  • "Which day do you most look forward to - your birthday or Christmas?"
  • "What's one thing you've always wanted to do but haven't had the chance to yet?"
  • "If you could live in any era, past or future, which one would you choose and what would you do?"
  • "If you could change one thing about the world, what would it be and why?"
  • "If you could master any skill or talent instantly, what would it be and how would you use it?"
  • "If you could have a conversation with your future self, what advice or insights would you want to gain?"
  • "What's something you've always wanted to learn or try but haven't had the chance to yet?"
  • "If you could have any profession or career, regardless of qualifications, what would it be and why?"
  • “If you could instantly learn any language fluently, which one would you choose?”

Disclaimers:

  • These questions are intended as inspiration. If they don’t feel natural to your personality or communication style, either adapt and revise them or don’t use them.
  • The examples above aren’t supposed to replace, but rather supplement standard first date questions.
  • Don’t ask questions one after the other. Use them as jumping off points to longer conversations.

This article is an excerpt from my online course:

Fearless Gentleman