- What’s the best thing that happened to you this week?
- What are you passionate about outside of work?
- How would your best friend describe you?
- What’s the last show you binge-watched?
- Are you a morning person or a night owl?
- What kind of music are you into right now?
- What’s the best trip you’ve ever taken?
- Do you cook, or are you a takeout person?
- What’s something you’re looking forward to?
- What do you do for fun on weekends?
Questions for him
Questions to Ask a Guy on a First Date
Want to really get to know him? These questions to ask a guy on a first date go beyond surface-level chat. From fun and flirty to deep and meaningful, these questions help you figure out if he’s worth a second date. Want these personalised for your date? Try our question generator.
Easy Openers (Questions 1–10)
10 questionsGetting to Know You (Questions 11–20)
10 questions- What’s a skill you’d love to learn?
- What’s your go-to comfort food?
- If you could live anywhere for a year, where?
- What’s the most spontaneous thing you’ve done?
- What book or podcast has stuck with you?
- What’s your favourite way to spend a rainy day?
- What’s on your bucket list?
- What’s something most people don’t know about you?
- What makes you laugh the hardest?
- What’s your hidden talent?
Going Deeper (Questions 21–35)
15 questions- What does a meaningful life look like to you?
- What’s something you’re proud of that has nothing to do with work?
- What’s the bravest thing you’ve ever done?
- What values matter most to you?
- How do you handle tough days?
- What’s a lesson you learned the hard way?
- What does home mean to you?
- Do you think people can truly change?
- What makes you feel truly seen?
- What’s a fear you’ve overcome?
- What does vulnerability mean to you?
- What do you wish more people asked you about?
- When do you feel most like yourself?
- What’s the best advice you’ve ever received?
- What are you still figuring out about yourself?
Romantic & Fun (Questions 36–50)
15 questions- What’s your love language?
- What does your ideal date look like?
- How do you know when you’re falling for someone?
- What’s a small gesture that means a lot to you?
- What’s the most romantic thing you’ve experienced?
- If you could have dinner with anyone, who?
- What fictional world would you live in?
- What’s your karaoke song?
- Dogs or cats?
- What’s the funniest thing that’s happened to you recently?
- If your life was a movie, what genre?
- What’s a trend you refuse to follow?
- What song makes you think of love?
- What would make tonight the perfect date?
- What’s one thing about you that you hope someone will love?
Tips for Using These Questions
- Start with the easy openers and work your way deeper
- Share your own answers — conversation is a two-way street
- Skip anything that doesn’t feel natural in the moment
- Follow up on interesting answers rather than rushing to the next question
Frequently asked
No! Pick 10–15 that feel right and let the conversation guide you. Quality beats quantity.
Great — that means you don’t need the list. Use these as backup, not a script.
Absolutely. They work just as well on Zoom, FaceTime, or any video call.
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