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First Date Questions & Icebreakers
Need first date conversation starters that actually work? These Would You Rather questions are perfect icebreakers for dating apps.
First Date Icebreakers
- 1.Would you rather always have the perfect conversation topic or always know the perfect time to end the date?Rate this question
- 2.Would you rather share your most embarrassing story first or hear theirs first?Rate this question
- 3.Would you rather accidentally spill your drink on the first date or have something stuck in your teeth all evening?Rate this question
- 4.Would you rather meet someone who texts too much or someone who barely texts at all?Rate this question
- 5.Would you rather have an amazing date with bad chemistry or an awkward date with great chemistry?Rate this question
- 6.Would you rather know immediately if there's a second date or enjoy the mystery of not knowing?Rate this question
- 7.Would you rather have your date show up 30 minutes early or 30 minutes late with a great excuse?Rate this question
- 8.Would you rather be overdressed for the date or underdressed?Rate this question
- 9.Would you rather go on a double date for the first meeting or meet one-on-one somewhere public?Rate this question
- 10.Would you rather have the date planned perfectly or be spontaneous and see where it goes?Rate this question
- 11.Would you rather laugh too loud at their jokes or accidentally not laugh when you should?Rate this question
- 12.Would you rather ask too many questions or talk too much about yourself?Rate this question
Getting to Know Someone New
- 1.Would you rather date someone who loves the same music as you or someone who introduces you to new artists?Rate this question
- 2.Would you rather be with a morning person or a night owl?Rate this question
- 3.Would you rather date a homebody who loves cozy nights in or an adventurer who's always planning trips?Rate this question
- 4.Would you rather be with someone brutally honest or someone who always spares your feelings?Rate this question
- 5.Would you rather date someone who plans everything or someone who's completely spontaneous?Rate this question
- 6.Would you rather be with a foodie who loves trying new restaurants or someone who cooks amazing meals at home?Rate this question
- 7.Would you rather date someone with a big friend group or someone with a few very close friends?Rate this question
- 8.Would you rather be with someone who loves pets or someone who loves plants?Rate this question
- 9.Would you rather date someone competitive about games or someone who lets you win sometimes?Rate this question
- 10.Would you rather be with someone who shares everything on social media or someone very private online?Rate this question
- 11.Would you rather date someone who works a lot but loves their job or someone with lots of free time in a boring job?Rate this question
- 12.Would you rather be with someone who calls or someone who only texts?Rate this question
Fun & Light Conversation
- 1.Would you rather go on a date to a fancy restaurant or a fun arcade?Rate this question
- 2.Would you rather watch a scary movie together or a romantic comedy?Rate this question
- 3.Would you rather cook dinner together and risk disaster or order your favorite takeout?Rate this question
- 4.Would you rather go mini golfing or bowling on a first date?Rate this question
- 5.Would you rather meet at a coffee shop or a cocktail bar?Rate this question
- 6.Would you rather take a cooking class together or a pottery class?Rate this question
- 7.Would you rather go on an outdoor adventure date or a museum date?Rate this question
- 8.Would you rather have a picnic in the park or dinner with a view?Rate this question
- 9.Would you rather play video games together or board games?Rate this question
- 10.Would you rather go to a concert or a comedy show for a date?Rate this question
- 11.Would you rather try escape room as a first date or karaoke?Rate this question
- 12.Would you rather go on a brunch date or a late-night dinner date?Rate this question
Building a Deeper Connection
- 1.Would you rather know your date's love language immediately or discover it naturally over time?Rate this question
- 2.Would you rather date someone with the same goals as you or someone with completely different but compatible dreams?Rate this question
- 3.Would you rather be with someone who challenges your opinions or someone who always agrees with you?Rate this question
- 4.Would you rather know all their past relationship history upfront or learn about it gradually?Rate this question
- 5.Would you rather date someone who prioritizes family or someone who prioritizes career?Rate this question
- 6.Would you rather be with someone emotionally expressive or someone more reserved but deeply caring?Rate this question
- 7.Would you rather date someone who moves fast in relationships or someone who takes things very slow?Rate this question
- 8.Would you rather be with someone who remembers every detail you share or someone who makes you feel heard in the moment?Rate this question
- 9.Would you rather know immediately if someone is 'the one' or enjoy the journey of figuring it out together?Rate this question
- 10.Would you rather date someone who pushes you out of your comfort zone or someone who accepts you exactly as you are?Rate this question
- 11.Would you rather have deep conversations on the first date or keep it light and save deep talks for later?Rate this question
- 12.Would you rather be with someone who forgives easily or someone who never forgets but works through it?Rate this question
How to Use These Questions on a First Date
Would You Rather questions work great for first dates.
- Start with light, fun questions to break the ice
- Ask a question and give your answer first
- Follow up with "why?" to keep the conversation going
Tips for Dating Apps:
- Use a question as your opening message instead of "hey"
Why Would You Rather Works for First Dates
Stand Out from the Crowd
A fun question immediately shows personality.
Reveal Compatibility
These questions naturally reveal values and preferences.