83 Dating Questions to Ask in the Talking Stage to Get to Know Them Deeper
Looking for the best dating questions to ask in the talking stage to build connection, spark flirting, and find out if they’re actually worth your time?
Dating questions to ask in the talking stage aren’t just icebreakers, they’re shortcuts to emotional intimacy, green flag spotting, and avoiding months of wasted effort.
In psychology, we know that the quality of questions in early relationships can determine how fast and deeply people connect. In fact, a well-known study by Arthur Aron and colleagues found that strangers who asked each other a series of increasingly personal questions reported significantly higher closeness, even falling in love after just 45 minutes.
📚 Source: The Experimental Generation of Interpersonal Closeness, Aron et al., 1997
Whether you’re texting, FaceTiming, or sitting across from each other with a drink, good talking-stage questions can reveal everything from emotional maturity to future compatibility, while keeping things playful and flirty. You don’t need a psychology degree to navigate this stage… but a few smart questions won’t hurt.
[Read: The Talking Stage: What It Is, How Long It Lasts and Signs & Ways to Get Past It]
So here they are: the best dating questions to ask in the talking stage, organized by themes that matter, so you can skip the small talk, spot red flags early, and build real chemistry.
Dating Questions About Core Values & Life Goals
These dating questions to ask in the talking stage help you figure out whether your values, goals, and lifestyle align, the kind of stuff that can either make love easier or turn it into a slow burn of mutual resentment.
1. Do you want kids?
This question is essential because it touches on one of the biggest lifestyle decisions a couple can face. You don’t have to agree immediately, but if your answers are completely opposite, it’s better to know early before emotional investments run deep.
2. If yes, how many?
It may sound light, but this question uncovers how strongly someone feels about parenting and their vision for the future. Someone imagining a big family might feel incompatible with a partner who’s hoping for just one (or none).
3. Do you think both partners should work?
This taps into expectations around gender roles, finances, and ambition. Whether you’re a hustle-all-day couple or value a more traditional setup, it’s better to talk about your outlook before assuming you’re on the same page.
4. Where do you see yourself in five years?
It’s a classic question for a reason, it tells you whether your paths align. Are they dreaming of van life and you’re picturing a mortgage and two Labradors? Then you might have some future-mapping to do.
Money issues are a leading cause of long-term relationship tension. This question isn’t about getting access to their finances, it’s about understanding how they view money, independence, and shared responsibility.
6. Have you ever lived with someone before?
Living with a partner is a different kind of intimacy, and someone who’s never done it might be less ready for that leap. This question also gives you insight into how they handle domestic dynamics and commitment.
7. Have you ever been in love?
It’s not about comparing histories, it’s about emotional availability. Someone who’s never been in love might not know how they behave in a serious relationship, while someone who has can reflect on what worked or didn’t.
8. Do you believe in God?
Faith and spirituality play huge roles in values, decision-making, and even how you’ll raise kids (if you want them). This question isn’t about judging beliefs, it’s about checking compatibility and openness.
9. Do you want to get married?
Some people see marriage as essential; others see it as optional or outdated. This isn’t a proposal, it’s just a way to check if you’re ultimately heading toward the same version of “forever.” [Read: 58 Best & Worst Reasons to Get Married & Signs You’re Not Ready For It]
10. Are you close to your family?
This opens up a window into their upbringing, emotional world, and family dynamics. It can also hint at what kind of relationship you might have with their family, or what kind of support system they have.
11. Do you want any pets?
It seems like a small thing, but wanting (or hating) pets can affect daily life and future planning. Plus, people’s attitudes toward animals often reflect their nurturing side and lifestyle preferences.
12. How important is your job?
This question shows where their career fits in their life hierarchy. Someone who lives for their job might value independence and long hours, while someone who sees work as “just a job” may prioritize relationships or leisure.
13. What are your biggest life goals?
A wide-open question that reveals what drives them, scares them, or lights them up. Whether it’s travel, success, service, or starting a family, it gives you a view into their heart’s direction. [Read: 17 Signs of a Supportive Partner Who Encourages You & Your Goals]
14. Do you intend to travel much in life?
Wanderlust is romantic, but not everyone shares it. This question reveals how open they are to adventure, change, and flexibility, or if they’re more of a homebody who loves stability.
15. What really irritates you?
Understanding someone’s pet peeves can save you a lot of future headaches. It also shows how self-aware they are and how they deal with discomfort, stress, or annoyance.
16. Are you an angry person?
It’s a bold question, but a necessary one. Emotional regulation matters in long-term relationships. Someone who owns their triggers and works on them is miles ahead of someone who deflects or blames.
17. Are you a text person or a phone call person?
This might feel trivial, but it points to their communication style, and whether it matches yours. Some people feel drained by phone calls, others feel ghosted by short texts.
18. Are you religious?
This can overlap with belief systems, but also includes values, rituals, holidays, and community. It helps you understand how their worldview might shape everyday life and long-term plans.
19. Is race important to you?
It’s a sensitive topic, but one that can’t be ignored, especially in multicultural dating. This question can bring up important conversations about values, upbringing, experiences, and openness.
20. Have you ever been addicted to anything?
Addiction, whether past or present, can influence a person’s habits, priorities, and emotional health. Asking with compassion can open space for honesty and show how open they are about their own growth.
21. Are holidays important to you?
This question is a sneaky way to ask about traditions, family involvement, and how someone sees celebration, downtime, and even spiritual connection. Some people go big, others couldn’t care less.
22. What city do you want to live in?
This is about lifestyle compatibility. Someone dreaming of an NYC skyline might clash with someone saving up for a quiet cabin in the woods. It also opens up dialogue about roots, change, and flexibility.
👉 Looking for more flirty questions to read their mind? Try these:
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Dating Questions About Love, Sex & Relationship Baggage
These questions dive into the real stuff, sex, love, and past relationships. They’re bold, sometimes uncomfortable, but incredibly revealing.
How someone talks about their exes, sex life, or heartbreaks says a lot about their emotional maturity, values, and how they might treat you. Some of these questions are playful, some are deep, all of them help you understand if you’re truly compatible in and out of the bedroom.
Just remember: it’s not an interrogation. These are convo starters, not confessions.
23. What’s the best date you’ve ever been on?
This question lets you peek into their love language and what makes them feel special. Whether it was a candlelit dinner or a goofy amusement park ride, it tells you what kind of effort they appreciate, and what memories they cherish. [Read: 45 Special & Sweet Date Ideas Every Couple Should Have on Their Checklist]
24. What’s the worst date you’ve ever had?
How they talk about this says a lot. Are they empathetic, funny, bitter, or judgmental? It gives you a sense of their attitude toward failure, awkward moments, and whether they blame others or see the humor in things.
25. Have you ever cheated on a partner?
It’s a tough one, but it matters. Their honesty and how they talk about past mistakes will show you if they’ve grown, or if they’re still dodging accountability. Just don’t ask this like you’re a prosecutor.
26. Have you ever had a threesome?
You’ll learn how adventurous, open, or experimental they are, or whether that kind of thing totally freaks them out. Not everyone’s into it, but it helps you know what kind of sexual history and preferences you’re working with. [Read: First Time Threesome: My Sexy Accidental Threesome While On Holiday]
27. What’s been your best relationship?
This isn’t about comparisons, it’s about understanding what “good love” looks like to them. What made that relationship work for them? What did they value, and are they looking for the same now?
28. What’s been your worst breakup?
Breakups reveal a lot. If they say “my ex was crazy” without any self-awareness, that’s a red flag. Look for signs of emotional growth, maturity, and how they handle loss and endings.
29. What’s your biggest sexual fantasy?
This one’s spicy, but only ask it if the vibe is right. It opens the door to desires, kinks, and whether you’re sexually aligned. It also helps build trust if they feel safe enough to share. [Read: How to Open Up About Sex & Get Your Partner to Share Their Desires]
30. Do you get bored after you sleep with someone?
This cuts right to emotional depth and sexual consistency. If they’re the type to chase novelty and dip, you’ll want to know that. If they value connection and chemistry, that’ll come through too.
31. Do you use condoms or birth control?
It’s not the sexiest question, but it’s crucial for safety and responsibility. Their answer shows maturity, awareness, and how they handle shared accountability in intimate situations.
32. Have you ever had an STD?
Again, a sensitive question, but a necessary one in adult dating. How they answer shows their openness, honesty, and approach to sexual health.
33. Are you circumcised?
Only go here if you’re both in a space where talking about bodies feels safe and normal. It’s not about judgment, just understanding what to expect and where their comfort zones are.
34. Do you have any children?
This is big-picture stuff. Kids change the shape of a relationship and someone’s priorities, and it’s important to know if they’re already a parent or navigating co-parenting with an ex.
35. Have you ever been married?
Understanding their relationship past helps set context. A previous marriage isn’t a dealbreaker, but how they talk about it tells you a lot about their perspective on commitment, growth, and endings.
36. If so, how many times?
This isn’t about body count, it’s about patterns. One marriage ending amicably is very different from a series of dramatic divorces with no self-awareness. Look for emotional insight, not just numbers.
37. When’s the last time you were tested?
This shows they care about safety, respect, and responsibility in their sex life. If they dodge this question or joke it off, you might want to think twice.
38. What’s the kinkiest thing you’ve ever done?
You’ll find out how adventurous or open they are, and whether their idea of “kinky” aligns with yours. It can be playful or profound, depending on the vibe. [Read: Top 50 Kinky Sex Ideas Worth Trying At Least Once in Your Lifetime!]
39. Do you use sex toys?
This reveals comfort with pleasure, openness to exploration, and how well they know their own desires. It’s also a smooth entry into talking about what turns you both on.
40. Are you a jealous person?
Their level of jealousy says a lot about emotional security and attachment style. If they admit to being territorial or triggered easily, that’s something worth unpacking before things get serious.
41. Do you believe men and women can be just friends?
This isn’t just about friendships, it’s about trust, boundaries, and how they view gender dynamics. Someone who thinks the answer is always “no” might struggle with insecurity or control.
42. What was your longest relationship?
This gives you a sense of their capacity for long-term love. Someone who’s never gone past a few months might be newer to commitment, and that’s not a red flag, but it’s good to know. [Read: 10 Relationship Stages Every Couple Goes Through: Month & Year Milestones]
43. What makes you feel sexiest?
Their answer here shows self-awareness and vulnerability. It also opens the door to mutual compliments and building sexual confidence together.
44. Are you into anal sex?
Not everyone’s cup of tea, but if it’s important to one of you, it’s better to talk about it than make assumptions. Honesty about limits and desires is what makes for a healthy sex life.
45. What’s better, kissing or hugging?
It’s playful, but surprisingly telling. Kissing often equals passion; hugging equals safety. How they answer reveals what kind of intimacy they naturally gravitate toward.
46. Do you ever have sex dreams?
This one keeps things light and flirty, while still being intimate. It shows whether they’re open to talking about subconscious desires, or if they avoid sexual convo altogether. [Read: How to Have a Wet Dream: 36 Ways to Have Hot Sex Dreams & Sleep Orgasms]
47. What would qualify as the “best sex ever”?
You’ll find out if they value emotional connection, novelty, kink, or chemistry. It’s a chance to see if your expectations align in the bedroom.
48. When’s the first time you remember being turned on?
A nostalgic, vulnerable question that often leads to funny or sweet stories. You’ll also get a glimpse into their early sexual development and openness to talking about it.
49. Are you a big flirt?
It’s a harmless question that reveals whether they see flirting as playful fun or a slippery slope. It also helps you understand how they interact with others, and what to expect if jealousy’s ever a concern.
50. What’s your favorite part of a woman/man?
This question blends attraction with appreciation. You’ll see what they find sexy, but also whether they focus on shallow things or something deeper, like expressions, energy, or connection.
Fun & Flirty Icebreaker Dating Questions
If you’re not up for deep conversations about life and love, these dating questions are for you. They’re fun and silly while still helping you to get to know one another.
These dating questions are also fantastic ice breakers regardless of the subject matter. Here are a few fun dating questions to ask each other.
51. What’s your go-to “this is so me” meme right now?
It’s current, effortless, and says a lot about their humor. Swapping memes is basically flirting now, so this one opens an easy lane for playful banter.
52. If we ordered takeout, what are you picking without even asking me?
Food preferences are personality shorthand. You’ll learn comfort foods, taste adventurousness, and how decisive they are when the hanger hits.
53. Perfect lazy Sunday: what’s on the agenda?
Vibes reveal values. You’ll find out whether they’re a brunch-and-walk person or a binge-and-nap goblin, and whether your downtime styles click.
54. Which tiny everyday thing makes you stupidly happy?
This spotlights gratitude and joy literacy. People who notice small delights tend to bring warmth and positivity into relationships.
55. What’s your most chaotic travel story?
A fun prompt that sneaks in problem-solving and adaptability. Do they laugh at mishaps or spiral? You’ll hear it in the story.
56. What song would you shamelessly karaoke even if the mic cut out?
Music is easy chemistry. Their pick shows nostalgia, courage to be goofy, and whether they’ll match your energy in public.
57. What’s your signature drink order?
Low-stakes, flirty, and useful for future dates. It also hints at taste, routines, and whether they’re more classic or experimental.
58. What’s your love language when it’s just friends?
Non-romantic love languages reveal how they show up for people in general. You’ll get clues about generosity, consistency, and empathy. [Read: 30 Little Qualities in a Partner That Secretly Predict Long-Term Love]
59. What’s the last thing you learned from a TikTok or reel?
Cute way to see their curiosity stream. You’ll learn interests and whether they feed their brain with hacks, humor, or hot takes.
60. What’s a silly hill you’ll absolutely die on?
It’s playful debate fuel. Watching how they defend a ridiculous opinion shows wit and how they handle light disagreement.
61. Which fictional couple makes you think “okay, that’s goals”?
Their answer reveals relationship ideals without getting heavy. You’ll hear what they equate with healthy chemistry. [Read: Couple Goals: 58 Fake & Real Ideas You MUST Add to Your Relationship Goals]
62. If we had a two-person team name, what would it be?
It’s collaborative and a little flirty. You’ll see how quickly they play along and co-create an inside joke.
63. What’s your most controversial snack combo?
Fun, low-stakes weirdness is instant bonding. It also opens the door to trying each other’s favorites on a date.
64. What’s a hobby you secretly want to be annoyingly good at?
Ambitions without pressure. You’ll spot curiosity, growth mindset, and a future date idea you can plan together.
65. What compliment do you love getting the most?
Great flirt runway. You’ll find out what makes them feel seen, which helps you tailor affection and banter.
66. If we got stuck in an elevator for 30 minutes, what’s your move?
Crisis-lite scenario tests humor and calm. Do they soothe, entertain, or engineer an escape? It’s personality in a micro-drama.
67. What’s your petty ick that you can laugh about now?
Silly icks are relatable and revealing. It shows standards without meanness, and whether they can laugh at their own pickiness.
68. What’s your favorite way to flirt over text?
This gets you free game plans. Are they voice notes, emojis, playful questions, or slow-burn replies? Now you know. [Read: 70 Sexy Texts to Send a Guy or Girl & Spark a Hot, Dirty Conversation Instantly!]
69. If I dared you to plan a spontaneous mini-date right now, what would we do?
Creativity + initiative check. You’ll see if they can spin fun out of nothing and whether your spontaneity levels match.
70. What’s a tiny green flag that makes you instantly more attracted to someone?
You’ll learn what they actually notice and value. It keeps the tone positive and gives you both easy ways to impress each other.
👉 Check out these flirty, dating questions if you want everyone to love talking to you!
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Dealbreakers & Compatibility Questions that Drop Clues
These questions are low-key lifesavers. Ask them to avoid future drama, spot mismatches early, and figure out if they’re on your same wavelength emotionally and practically.
71. What’s a non-negotiable in a relationship for you?
This gets straight to the heart of what they absolutely need, or will never tolerate. It tells you what they’ve learned from past relationships and where their lines are firmly drawn. [Read: 20 Non-Negotiables in Relationships You Shouldn’t Ever Compromise On]
72. How do you usually deal with conflict?
Forget how romantic they are, how they argue says way more about long-term potential. Do they shut down, explode, or talk things through? You want someone who knows how to handle tension with care.
73. What’s your ideal communication style in a relationship?
This question reveals how they stay connected, texts all day or deep chats at night? You’ll learn what they consider “enough” and whether that matches your emotional bandwidth.
74. How important is physical affection to you?
Compatibility isn’t just mental, it’s physical too. Knowing if they’re cuddly, PDA-prone, or more reserved helps avoid mismatched touch expectations.
75. Do you believe in soulmates?
It’s not just a rom-com question, it reflects their outlook on love, destiny, and whether they’re chasing something idealized or grounded.
76. What’s your attachment style?
This one might feel psychology-nerdy, but it’s actually super revealing. If they know they’re avoidant, anxious, or secure, that self-awareness can make or break your emotional dynamic. [Read: Attachment Styles Theory: 4 Types and 19 Signs & Ways You Attach To Others]
📚 Source: Attachment theory, Bowlby, Ainsworth et al.
What NOT to Ask in the Talking Stage
Look, not all questions are good questions, especially in the talking stage. Some things are better saved for later (or never). Here’s what to not ask too soon, unless you want to trigger a disappearing act.
1. How much money do you make?
It’s too personal, too soon, and makes it sound like you’re interviewing them for a joint mortgage. There are better ways to understand financial compatibility later on.
2. Why did your last relationship end?
This one gets heavy fast. Let the past unfold naturally instead of demanding a trauma dump before the drinks even arrive.
3. How many people have you slept with?
Unless you’re already in an exclusive phase, this can come off as invasive, insecure, or judgmental. Focus on current values, not body counts.
4. Are you talking to other people right now?
It’s fair to wonder, but the talking stage is inherently casual. If exclusivity matters to you, bring it up when you’re ready to define the relationship, not before. [Read: Exclusive Relationship: 43 Signs You’re in One, Or Totally Ready for It!]
5. Are you in love with your ex?
Asking this rarely leads to a useful answer, just awkwardness. Time and observation will tell you if they’re emotionally available or still stuck in the past.
6. When do you think we’ll get married?
Unless you’re both clearly on the same “looking for something serious” wavelength, this question screams premature fantasy. Focus on connection first, long-term plans come later.
7. Do you want kids… with me?
Asking if they want kids in general? Fair game. Asking if they want kids with you after two FaceTime calls? Please log off.
👉 Looking for relationship questions? Try these!
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The best kind of dating questions bring you closer, not just answers, but insight
You don’t need to fire off all questions like it’s a personality exam. Just keep a few of your favorites in your back pocket, the playful ones, the deep ones, the “this-matters-to-me” ones. Drop them in when the vibe is right, and you’ll learn more in one conversation than weeks of small talk.
Because the right dating questions don’t just help you find out who they are, they help you figure out how you feel around them.
And that? That’s where real connection starts.
[Read: 50 cheeky, personal questions to ask someone you like]
Who you decide to crown your official boyfriend or girlfriend is a big deal! We hope these dating questions can help you seal the deal on whether or not the person you’re dating is relationship-worthy.
