Select Page

144 Great Conversation Starters – Spark great conversations.

144 Great Conversation Starters – Spark great conversations.

New? Start here. | This post contains affiliate links. That means that we receive a commission for purchases made on them (more info).

Knowing conversation starters, designed to start the right kind of conversations, is essential… because like we’ve all experienced:

Kicking off a solid discussion can be tough. Whether you’re hanging with old friends or meeting new acquaintances, sometimes we all draw a blank. Not anymore.

We’re here to be your one-stop guide for all types of conversation starters.

This list of questions to ask will help you to eliminate those awkward silences and keep the conversations flowing. After all, one simple question can lead to in-depth discussions, and meaningful conversation is the root of any lasting relationship.


15 Best Conversation Starters

These conversation starters are the cream of the crop. They’re super versatile, and they can definitely spark some fascinating discussions. At the same time, they’re not intrusive, so they’re great for casual settings or to lead to some getting to know you questions.

These are such good conversation starters because they’re open-ended. They can lead to hilarity, poignancy, and everything in-between.

Here are the 15 best conversation starters:

1. What’s your favorite thing to do with your friends?

This question immediately sets a positive mood. After all, spending time with friends and loved ones is what life is all about. Show you’re interested in their extracurricular activities, while making it easy for them to come up with a response.

2. When you were a kid, what movie did you watch constantly?

We all have those nostalgic memories of watching that old VHS or DVD over and over. This question gives the other person the chance to talk about something fond and familiar.

3. If you had to sum up the internet in one word, what would it be?

There’s no denying the effect that the internet has had on the world. What’s their take?

4. What do you do when you’re not working?

What people do in their free time says a lot about them. This is one of the best conversation starters because it works for nearly anyone, and it gives the other person an easy topic to talk about.

5. If you could have an all-expenses paid trip to see any famous world monument, which monument would you choose?

Would they prefer to stay local or see the world? There are a lot of spectacular sights out there, and their preferences say a lot about their interests and the type of person they are in general.

6. Aside from TV/reading, what’s your favorite indoor activity?

What might you find them doing on a rainy day? In addition to learning about the person you’re talking to, you might even find some inspiration to pick up a new hobby.

7. If you could only wear comfortable or fashionable clothing for the rest of your life, which would you choose?

This conversation seems pretty straightforward, but it provides valuable insight into the person’s riorities. What’s more important — looking good or feeling good?

8. If you could only eat at one restaurant for the rest of your life, which would it be?

Food is always an easy conversation topic to digest. Plus, you may learn about a new local eatery where the two of you can wolf down some culinary magic.

9. If you could only be called your name or your nickname for the rest of your life, which would it be?

A person’s title changes the world’s perception of them, and it can shape their destiny. What someone prefers to be called can show their serious or humorous side.

10. Morning person or night owl?

Some people rise at the crack of dawn to grab those tasty early morning worms, while others prefer to paint the town red under the cloak of moonlight. What’s their M.O.?

11. If you could go on a cross country road trip with famous person, dead or alive, who would it be?

This is a such a good conversation starter because the potential for discussion is limitless. You can discuss why they would choose that person, what they would do, what they would hope to learn, and so on.

12. What you consider to be the most incredible job in the world?

This is a very revealing question. Would they find joy in helping others, or is money the primary motivator? Would they love to get paid to pursue their hobbies, or keep their professional and personal lives separate?

13. The most annoying?

There are lots of tough jobs out there, but somebody’s gotta do’em. This question can help you to understand what types of jobs they truly despise, and it can give you both some valuable perspective on your own lives, society, and the world as a whole.

14. Would you rather travel every day for the rest of your life, or never be able to travel?

Some people are homebodies, and others can barely stay put for a week. Would they rather live a comfortable life or an adventurous one?

15. If a song played every time you entered the room, what would it be?

While this question can definitely lead to some solid laughs, it also shows you how other people view themselves. After all, music creates an atmosphere and changes your mood — whether it’s melancholy, exuberant, or somewhere in-between.

20 Best Funny Conversation Starters

These lighthearted questions help you to connect through humor. Laughter is one of the most powerful tools for connecting with someone. If you can make someone laugh, you’ll probably end up becoming friends.

Use these funny conversation starters to start things off on a positive note. Or, use them to shift the mood after a serious discussion. It’s always wise to have at least a couple amusing questions in mind. They’re more useful than you might expect.

Here are the 20 best funny conversation starters:

16. What is an activity that never looks cool?

Reaching your right hand into your left pocket? Chasing a dollar blowing in the wind? Taking a selfie with an iPad? Bonus points if you attempt to prove the other person wrong.

17. If you were transported 400 years into the past with no clothes or anything else, how would you prove that you were from the future?

You can really get creative with this one, especially if one of you pretends to be a 17th century skeptic.

18. If animals were as intelligent as humans, what types of jobs would certain animals be uniquely qualified for?

Imagining animals integrating into human society is a recipe for laughter. What types of wildlife would you expect to see in the office or warehouse, and why?

19. If you had to be named after a city/state/country, which would you want it to be?

Be careful — this conversation may end up giving you both new nicknames.

20. What country do you think is the strangest?

The world is a fascinating and often peculiar place. Which culture just seems bizarre, compared to life at home?

21. What job doesn’t exist now but will exist in the future?

Will humans be reduced to robot polishers? Or will there be intergalactic salesmen? What career opportunities can we look forward to?

22. Would you rather be able to control fire or water?

Is the other person cool or hot? Keep the conversation going by volunteering to control the other element, and then argue about who would win in a battle.

23. Time or space?

Or spacetime? Be careful — while definitely a good conversation starter, it might lead to a discussion that could blow your mind.

24. Shape shift or mind read?

Would they prefer to control the physical or mental realm? What would they do with said powers?

25. What’s your favorite cheesy pick-up line?

There are some seriously bad ones out there. What’s the best pickup line that’s so terrible that it’s hilarious?

26. Who would be the worst person to be stuck in an elevator with?

You can expand on this question and make it anyone alive or dead. For the sake of discussion, dead people would be brought to life before entering the elevator.

27. If you could break any world record which one would it be?

The possibilities are endless. Would you accrue the largest garden gnome collection? Or, perhaps blowing the largest bubble gum bubble is your life goal. Anything is possible if you truly believe.

28. If you were offered the position of mayor of your city, would you take it?

What could possibly go wrong?

29. Do you think Captain Planet would make a good drinking buddy?

Is he your hero or a zero? How many times do you think he would he cheers to “our power combined” throughout the night?

30. If you could date any celebrity, who would you choose?

Out those celebrity crushes.

31. If you could get drunk with any historical figure, who would it be?

And would you do it on their turf or bring them forward in time to your favorite dive bar?

32. You’re locked in the mall overnight. What do you do first?

Do you hit the food court for the ultimate fast food feast? Go for a cruise in the raffle car? Take a swim in the fountain?

33. Space exploration or ocean exploration?

Spaceships or submarines? Extraterrestrials or regular terrestrials? The ocean is vastly unexplored, but so is space. Which one is their final frontier of choice?

34. If your parents let you name yourself when you were five years old, what would your name be?

Pikachu? Mashed Potato? Fire Truck? Batman? This question will have you both in stitches, and it also lets you know what kind of kid they were.

35. What was your biggest fashion faux pas to date?

There’s no shame in it — we’ve all made some style blunders. Which outfit was simply unforgivable?

20 Best Conversation Starters with a Girl

Whether she’s your longtime bestie or a new crush, starting a conversation with a girl can be seriously nerve-wracking. However, it really doesn’t have to be.

It’s important to remember that while the two of you may be different in some ways, at the end of the day, you’re both human beings, and you probably have a lot more in common than you may think.

Girls can sense when you’re trying too hard, so play it cool. Be genuine and confident, and try to connect with her just like you would with one of your guy friends. Of course, if want to get a girl to like you, eventually you’re going to need to add in those romantic vibes. Just don’t don’t overdo it too fast. Pay attention to see if she’s showing you signs she likes you.

Girls can give you a unique perspective that you won’t get from your bros. Some of the best conversations you’ll ever have will be with people who have different life experiences.

Use these questions to ask a girl to connect with her, and also to learn. Forming a bond with the fairer sex can be more challenging at times, but the results are worth the effort.

Here are the 20 best conversation starters with a girl:

36. What do you do on a rainy day?

Some people like to curl up with a good book or a movie. Others have indoor hobbies. Learn about how she spends her time when the weather is dreary.

37. Coffee or tea?

What is her hot beverage of choice? Either way, be sure to take her out for one.

38. How important is fashion to you?

Some people love picking out new outfits, while others find getting dressed in the morning to be a hassle.

39. If you could have a full scholarship to any university, what would you choose to study?

This a good conversation starter to help you understand what her true passions are.

40. Where is your favorite place to escape to?

Where is her happy place? If possible, bring her there. If not, use her answer as inspiration for your next date.

41. What’s your spirit animal?

It’s kind of a silly question, but the answer can actually be quite revealing. After all, there’s a big difference between a lion and a snake.

42. Do you think that age matters in a relationship or that it’s just a number?

Of course there are obvious limits, but where does she draw the line personally? Would she date someone younger or older?

43. How important is family to you?

A person’s relationship with their family says a lot about them. However, don’t be too quick to judge — sometimes there are legitimate reasons why she may not have the strongest connection. If she doesn’t want to talk about it, don’t push the issue.

44. What activity calms you down the most?

Painting? Yoga? Knitting? What does she do when she really wants to unwind?

45. Which parent are you closer to? Why?

Understanding her home and family life is a great way to get to know her better.

46. What’s something you to do the old-fashioned, non-tech way?

Sometimes the classics are classics for a reason. Does she prefer a paperback over an e-reader? Or maybe she loves vinyl records instead of MP3s?

47. What’s your favorite childhood memory?

This conversation immediately conjures warm feelings and gives her the chance to talk about a special time in her life.

48. Have you ever been on a blind date?

This question can lead to some hilariously traumatic stories.

49. What’s the worst first date you’ve had?

You’re probably going to get to hear some horror stories. Learn from them, and never make the same mistakes.

50. Do you plan an exit strategy on first dates?

This can be an interesting question to ask on a first date.

51. What one quality do all your friends have in common?

Understanding the type of people that she surrounds herself with provides valuable insight into her own personality, as well as the qualities she values in a person.

52. What’s your go-to drink/food/activity when you’re sick and in bed?

Take note, and be sure to be prepared next time she’s feeling under the weather. You’ll win some serious points.

53. If it was socially acceptable to dress in the garb of any time period, which would you choose?

Would she pull a Costanza and drape herself in velvet? Or perhaps she’d prefer the charming fashion of the Victorian Era?

54. What is the worst pickup line you’ve heard?

Bust it out some other time for a laugh.

55. What is the best dessert you’ve ever tasted?

What’s the most decadent, mouthwatering post-dinner treat she’s ever devoured? Follow-up question: What’s the best dessert she can fathom that she’s never tried (or that doesn’t even exist)?

15 Best Conversation Starters with a Guy

Whether you’re working a long shift with a new co-worker or getting drinks with your Friday night crew, having some questions to ask a guy to get to know him on deck helps to keep things interesting.

These questions are focused on common interests that guys tend to share, but don’t be afraid to go outside the box too. Sometimes a question from left field can lead to hilarious or fascinating results.

Some of these questions can be divisive, so don’t be surprised if a good-natured argument arises. Sometimes, you may need to agree to disagree.

Here are the 15 best conversations starts with a guy:

56. Which historical man do you respect most?

Whether he’s a war general or an activist, you’re in for a fascinating conversation. You may even learn a thing or two.

57. Would you rather fight a grizzly or a swarm of hornets?

And what would your fighting strategy be?

58. What game or movie universe would you most like to live in?

There are a lot of awesome settings out there. Would he prefer an intergalactic space colony, or perhaps the blissful ignorance of existing in a Matrix-style simulation?

59. If you could have any car in the world, what would it be?

This is a straightforward question — what’s his ultimate dream ride?

60. Scotch or beer?

There’s no wrong answer to this question, and that includes “both.”

61. What’s your sport?

This is another simple, direct question that can spark a massive conversation.

62. Star Wars or Star Trek?

What’s his favorite space franchise? Don’t be afraid to geek out. This conversation may get heated!

63. Marvel or DC?

Which comic universe does he prefer? The answer might be heavily rooted in his childhood. Hopefully you have opposing views so you can convince each other that you’re right.

64. If you could choose to be immortal, would you?

Living forever seems like a no-brainer at first, but when you think about it, immortality has its drawbacks. For example, if you truly never die, there’s a strong chance that you might eventually get stuck somewhere uncomfortable for a long time. Remember: There are no other super powers involved.

65. Who is your favorite character in a movie, and why?

We all have our favorite film characters. Is he an action star? A martial arts wizard? A celebrity crush?

66. What was the most dangerous situation you’ve ever been involved in?

You can be sure that this conversation will be interesting. When did he feel most vulnerable, and how did he overcome that situation?

67. If someone asked you to give an impromptu Ted talk, what would you talk about?

Is he secretly an expert on some random topic? Or would he fake it? What do you do when you’re put on the spot like that?

68. If you could instantly master any skill, what would it be?

The possibilities are endless. If you want to make it more interesting, the skill can also be superhuman.

69. Do you have any collections?

A person’s collections say a lot about their interests and the life they’ve lived up to that point.

70. Do you believe in paranormal experiences? If so, have you ever experienced one?

Ghosts, aliens, and Sasquatches — oh my! Has he ever had an experience that he simply can’t explain, no matter how badly he may want to? Demand honesty.

20 Best Conversation Starters for Couples

Sometimes relationships get a little bit stale. It’s not ideal when that happens, but when you spend a lot of time with someone, it’s totally normal to run out of things to say.

Good conversation is essential to any long-term relationship — platonic or romantic. These conversation starters for couples keep the lines of communication while also helping you to learn more about each other.

Next time you don’t know what to say at dinner, bust out one of these handy questions for couples. Just one solid conversation starter can really bring two people closer together.

Some of these questions seem surface-level, but they can really lead to in-depth discussions. Others are designed to help you strengthen your relationship and help you both to understand each other’s desires and needs. Pay close attention to her answers.

Here are the 20 best conversation starters for couples:

71. Do you dream?

Dreams are fascinating. They can also reveal a person’s inner-workings. Talking about dreams is a great way to open the door to other conversations about your partner’s current state of mind.

72. What was your last dream about?

This is the natural follow-up question to the previous one. Talking about your dreams can help you to understand them (and each other) a little bit better.

73. What do you usually think about on your commute home from work?

Just asking her what she thinks about shows her that you care.

74. What accomplishments are you most proud of?

Everyone likes to toot their own horn a little. Give her a platform to talk about the things she has done that make her happy.

75. What are some of your greatest hopes?

Inquiring about her hopes and dreams shows that you’re interested in being with her for the long haul.

76. What are the top three best things a boyfriend can do to make you feel special?

Just asking this question is going to be a great starting point. Remember what she said, and make it a point to do them.

77. What kind of physical affection do you like?

Knowing what floats her boat is beneficial for obvious reasons. Stop guessing, and get the scoop straight from the source.

78. What do you think I’d say is your most attractive quality?

This question is great because it’s a win-win. If she’s right, that’s great. If she’s wrong you just complemented another feature.

79. If you could pick the gender of your child, would you?

Does she have a preference?

80. If you could give you children one talent, what would it be?

This question is a great way to find out what kind of hopes and dreams she has for her children, as well as herself.

81. What one word you use to describe our first kiss?

Hopefully that word is something along the lines of “magical,” not “horrifying”.

82. What’s the earliest memory that you remember?

It’s always interesting to look back at those early, hazy memories.

83. What one thing makes our relationship better than other relationships?

There’s nothing wrong with gloating a little. What makes you two the ultimate power couple?

84. If you could only have one, spontaneity or stability, which would you pick?

Her answer really says a lot about her, her motivations in life, and what kind of future she hopes to achieve.

85. Where do you go/what do you do when you need inspiration?

We all have our own methods for getting inspired. What are her tricks?

86. If a genie gave you three wishes, what would they be?

This question is fun and lighthearted, but it also shows what’s most important to her.

87. What’s your most comforting comfort food?

Bonus points if you prepare it for her on her next day off.

88. What does your dream home look like?

Is she hoping for a mansion in the Hollywood Hills or a quaint cabin in the woods?

89. If you were stranded on a desert island with plenty of water, food, and shelter, what one luxury item would you want?

This is a fun question that really makes you think about what’s important.

90. What’s the most meaningful complement you’ve ever received?

This conversation starter helps you to understand what she considers her best and most important features. Her response can also inspire you to give meaningful complements beyond her physical appearance.

20 Best Deep Conversation Starters

When you’re ready to move from the more relaxed questions into more profound or heartfelt territories, try these deep conversation starters.

These questions aren’t always appropriate, so use them carefully. For example, if you’re having lunch with your your boss or dinner with a first date, you may want to avoid these personal questions.

Use these deep questions to ask when the mood feels right. Maybe you’ve shared some laughs, or you’ve opened up a bit to the other person. This is going to be a reciprocal conversation. If you’re not ready, or if you’re not sure if they are, hold off.

Here are the 20 best deep conversation starters:

91. What skill do you wish more people took the time to learn?

Which skill is personally rewarding? If you want to go even deeper, which skill would improve society as a whole if more people took the time to learn it?

92. What is the biggest waste of time in your life?

We all do things that aren’t exactly productive. At the same time, if it makes you happy, is it really that bad? Sheryl Crow would say no.

93. What one thing in life should always be free?

What is the quintessential item that should be a human right? Water? Food? Shelter? This question can spark an in-depth conversation about society and what it means to be a member of the human race.

94. What is something that can’t be taught and can only be learned with age?

Some things are only learned through first-hand experience. Talking about them can help you to gain new perspectives.

95. What is increasingly becoming socially acceptable, but shouldn’t be?

Is the world going to hell in a handbasket, or are the times just a-changin’? Discuss shifts in social norms and how they affect individuals and the society they live in.

96. What one job do you think computers/machines will never replace?

Artificial intelligence will replace many jobs in this decade alone. What career choice will always require that human touch? Will AI ever become so advanced that humans are irrelevant?

97. Who do you compare yourself to most?

Understanding how someone views themselves sheds light into who they are. After all, the people you admire say a lot about who you are and who you strive to be.

98. Is there something you stopped doing, even though you love it? Why’d you stop?

People change. Sometimes they give up on hopes and dreams. This conversation can be a bitter pill to swallow, but it can lead to positive change, Approach it in a motivational way — not judgmental.

99. Are you the type of person with lots of friends or just a few close ones? Why?

Are they the type of person with a thousand best friends, but nobody to call when they need someone to lend an ear? Or, are they the type to hold close friends dear and try not to spread themselves too thin?

100. Where have you gone and felt the most out of place?

Most people have felt out of their element at some point. Talk about those times and how they altered your life perspective.

101. Who or what is the greatest enemy of mankind?

This existential question really makes you think about the fragility of the human species, and how fortunate we are to exist at all.

102. What does love mean to you?

Love is difficult to define. It’s a relative term that means something different to many people, and that meaning can change based on personal experiences.

103. What or who would you sacrifice your life for?

What’s bigger than you? What would it take for them to make the ultimate sacrifice?

104. What do you wish your brain was better at doing?

We could all use a little self-improvement in some way or another. Discussing shortcomings is a great way to get motivated to overcome them.

105. What are your dating red flags?

What are the signs that make them wary? They may not be deal-breakers, but they do make you think twice.

106. Are you an optimist, a pessimist, or a realist?

How do they view the world? Is the glass half-full, half-empty, or is it simply nothing more than a half-filled glass?

107. Would you rather never get angry or never be envious?

Negative emotions happen to the best of us. Would they rather eliminate feelings of rage or jealousy?

108. If you could rid the world of one disease what would it be?

It’s a dark question that may come with personal answers and reasons.

109. What is your current life mantra?

This question can help you to see the world through their eyes, and it can provide you with some valuable wisdom to incorporate in your own life.

110. Are humans more creative or destructive?

It’s clear that human beings are highly capable of building up and breaking down. Which one defines us more?

15 Best Text Conversation Starters

Texting with someone is a surprisingly effective way to get to know them. You have time to think about what you say and choose each word carefully. You can also be a bit bolder than you might be face-to-face.

If your texting game is a bit weak, these questions to ask a girl over text will help. Don’t ask one and then ask another right after. Start with text conversation starters, and then roll with it. If the conversation starts to die down, then use another one.

Your phone can be a powerful social tool, but it can work against you if you’re not careful. Don’t be that guy who texts incessantly. You don’t want to come off as needy or overly clingy.

Sometimes people don’t see texts until later. Sometimes they get busy and forget to respond. Don’t overthink it.

Texting is an art. Sometimes the best play is to not play at all. Know when to let the conversation die naturally, and if she doesn’t respond, don’t text her again until she does.

Texting is fun, so keep it light and playful. Never argue over text. It’s easy to make assumptions when there’s no body language involved.

Here are the 15 best text conversation starters:

111. What’s your weirdest talent?

It’s the little idiosyncrasies that make people so special. This is a fun question that helps you to learn the little details about someone that you probably wouldn’t have found out about otherwise.

112. If you could only shop at one store for the rest of your life, which would it be?

No, the internet doesn’t count as a store.

113. What’s the best photograph you’ve ever taken?

This is a fun question because hopefully you’ll get to see the photo. If you’re not already connected on social media, this question can be a great way to approach it.

114. What’s your guilty-pleasure Netflix show?

Hey, sometimes you just want to watch something terrible, and that’s just fine.

115. Are you a dog or cat person?

It’s a classic question that never fails to get a response.

116. What do you consider to be your best physical feature?

There’s nothing wrong with a little vanity sometimes. If you’re texting with a romantic interest, this can be a great lead-in to complement her.

117. What’s the last TV show you binged?

If you’ve seen the show, you’ll have plenty to keep texting about. If not, you can ask her to give you a spoiler-free summary. Maybe you’ll end up with something new on your Netflix list.

118. What was your first thought this morning when you woke up?

It’s a random question that can send the conversation in virtually any direction.

119. Do you believe in horoscopes?

Either way, discussing your horoscopes and finding how they fit your life can be fun, whether you actually take them seriously or not.

120. What’s the most daring thing you’ve ever done?

When was the adrenaline pumping hardest? You’ll probably get an entertaining story out of this question.

121. Have you ever had a terrible roommate?

Bad roommate stories are almost always hilarious.

122. What’s the last decision you regretted?

We all make mistakes. You might want to balance things out by asking about decisions they’ve made that they’re proud of.

123. What is the most annoying thing to you?

We all have little (and big) things that get on our nerves. Discuss them, but never do them.

124. Do you have any phobias?

Talking about fears can help you to get over them.

125. If you had the resources to invent anything, what would it be?

A faster microwave? Batteries that never die? An actual hover board? Get creative — the world needs you!

19 Best Conversation Starters for Online Dating

Online dating is quickly becoming the new norm. Plenty of people would rather get to know someone digitally before wasting their time at the coffee shop.

Charming a girl with just words and emojis can be a struggle — to say the least.

It’s important that you find that balance between flirty and friendly. You want the other person to know that you’re interested, but you don’t want to come on too strong or weak.

Being too pushy is the fastest way to turn that right swipe into “you’re not my type.”

These great conversation starters are perfect for keeping her interested so you can land that elusive IRL date. They also help you to get to know her better, so you can decide if she’s an ideal match.

Here are the 19 best conversation starters for online dating:

126. What do you do for fun?

Simple and direct. If her interests don’t vibe with yours, it may be best to call it off. If it sounds like you’d click well, ask her on a date based on her response.

127. Were you named after anyone?

This question is a bit out of left field, and that’s a good thing. After all, you want to stand out from the rest of the herd. This question also shows that you’re interested in her beyond just physical attraction.

128. What was the best book or series that you’ve ever read?

Discussing literature is a great way to flex your intellectual side while you learn about her tastes.

129. Do you have any tattoos?

Tattoos often come with great stories.

130. If you could only eat one pizza topping for the rest of your life, what would you choose?

Be careful, this question can be a deal-breaker. You might want to wait to discuss pineapples on pizza until you’ve already gone on a few dates.

131. Would you rather go on vacation for a month next year or have one week paid vacation now?

This question helps you to understand where she’s at in her life right now. It also says a lot about if she’s more of a spontaneous person or a planner.

132. Would you rather live in a place where it is always hot or always cold?

There are always air conditioners and heaters, but what’s her ideal climate?

133. Would you rather not be able to stop dancing or not stop singing?

Either one would make for some weird looks when she enters a room.

134. Would you rather have a family of 12 children or never be able to have children at all?

This is an indirect and humorous way of finding out what her thoughts on having a family someday are.

135. Would you rather be locked in an amusement park or a library?

This question helps you to understand if she’s more into intellectual endeavors or partying.

136. Would you rather eat pizza or ice cream as the only food for eternity?

While eating one of them forever sounds wonderful at first, this is actually a very cruel question because it means she would never eat the other one again. And what about tacos?

137. Would you rather date someone you met online or go on a blind date?

Hopefully her answer is online, but if not, maybe you can convince her to change her opinion.

138. Would you rather have free Wi-Fi wherever you go or have free coffee where/whenever you want?

What’s her favorite on-demand amenity? Does she need to stay connected at all times, or does she prefer an instant caffeine buzz?

139. Wine or beer?

Be sure to remember her answer when you take her out.

140. What TV show are you hooked on?

Hopefully you’ve seen it too so you can discuss it. If not, you have something new to binge. Pro tip: Ask which episode she’s on so you don’t accidentally spoil her watching experience (and your chances of taking her out).

141. If you had to become part of a TV-sitcom, which would you choose?

Follow-up: Which character would she be, and why?

142. Would you rather be a world-renowned chef or artist?

Does she crave congenial culinary creations or prefer prepossessing paintings and photography?

143. Where’s the coolest place you’ve ever been?

Getting a stranger to open up online can be a challenge. People love talking about their favorite experiences. Whether it’s a local hot spot or another country, she’ll love telling you about that one place that’s too cool for school.

144. What is your typical weekend like?

Although it’s a lighthearted question, the answer is important. After all, if you’re going to date someone, you want to be on similar wavelengths as far as how you spend your free time.

How to Start a Conversation

The art of starting a conversation is never fully set. Each and every interaction is an opportunity to refine your approach. Like anything in life, the more you practice, the better you get.

If you want to make a splash, the first step is to dive in.

Here is how to start a conversation:

1. Play it safe when necessary

The first rule as you learn how to start a conversation effectively is don’t push your limits.

With that said, don’t be too timid either. There is a time and place to be bold. Try to tow the line between keeping your company interested without crossing a line into uncomfortable territory.

If you don’t know someone well, stick with surface-level conversation starters. Of course, if you’re with a close friend, you can probably get a little more personal. When in doubt, play it safe.

2. Use conversation starters sparingly

Yes, having a brain full of good conversation starters can be empowering. You may be tempted to ask question after question. Don’t do it.

You don’t want to over-saturate the conversation. Quality is more important than quantity.

Choose one topic, and stick with it. You’re not playing 20 questions here. These are starters, and they should be used to do exactly that — start conversations.

3. Participate in the discussion

Once you start the conversation, your role isn’t over. In fact, it’s only just begun. As the one who initiated the conversation, it’s up to you to keep it moving.

Ask the person you’re with to elaborate on points. Give your own responses. Conversation is a two-way street.

4. Be a good listener

While you do want to participate in the conversation, sometimes you need to know when pipe down and let the other person speak.

You want the other person to feel comfortable opening up to you, and if they think you’re not listening, that’s not going to happen.

Don’t just hear what the other person is saying. Genuinely absorb the words they’re saying. Take the opportunity to learn about them, yourself, and whatever the topic of conversation may be.

A good conversation can be an eye-opening, rewarding experience. Don’t take that for granted. Don’t get so caught up in facilitating a good conversation that you forget to enjoy it.

Appreciate the impromptu verbal dance that makes a truly memorable conversation feel natural and inspired.

5. Pay attention to body language

There are verbal and non-verbal cues to keep in mind during the conversation. If the other person seems to be fidgeting or looking around, they may be uncomfortable. Know when to let the conversation die.

Also, be mindful of your own body language. Even if you mean well, glancing at your phone, tapping your foot, or lacking eye contact can make the other person self-conscious.

Eye contact and the occasional nod or “mhm” can go a long way in showing your company that you’re still there with them. You bought the ticket, so make sure they know you’re taking the ride.

6. Mix it up

After a deep conversation, you may be tempted to go even deeper or even more philosophical. That can work in some cases, but usually it’s best to lighten the mood. Conversely, after you’ve been sharing some laughs, a more intelligent, deep conversation may be a welcome change.

Contrasting conversations can be complementary. Pay attention to the overall mood, and mix it up when it feels right.

Downloadable List of Conversation Starters

Here is a downloadable list of conversation starters (right click the image and select Save Image As…):

Looking for More Great Questions?

At this point, you should be fully prepared to kick off a conversation in virtually any social situation. At the same time, it never hurts to update your mental question cache. After all, variety is the spice of life! We’ve got you covered.

Here are some more fantastic questions you can use to get to know someone better:

  1. We have an awesome list of Questions to Ask a Girl next time you’re silenced by her beauty, as well as plenty of Questions to Ask a Guy when you’re brain’s running dry.
  2. These Would You Rather Questions are perfect when you want to pass the time. They force you to think outside-the-box, and you can really get creative with them.
  3. Perfect for long car trips, the classic 21 Questions Game gives both participants the opportunity to flex their deductive reasoning skills.

In Conclusion

The gift of gab doesn’t always come easy, but these good conversation starters will certainly help. Now that you have plenty of solid questions to ask, it’s up to you to steer the ship and keep it on course.

If you’re going to initiate a conversation, be confident. These starters are the spark that gets the fire going, but you need to fan those flames into a raging inferno. Ask relevant follow-up questions and give your own perspective.

Don’t feel pressured to force conversations at all times. Sometimes, there’s nothing wrong with comfortable silence.

Be relaxed, authentic, and inquisitive, and you’ll find that discourse becomes more and more natural. A good conversation is one of the finer things in life. Savor it, and allow it to blossom organically.

About The Author

Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on, iHeart Media, Elite Daily, and The Urban List. Jasper lives in Georgia with his new bride.

Daily Quote

Skip to content