165 Best Conversation Starters: Funny, Deep, Flirty & More

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Easy ice breakers for parties, networking events, first dates & beyond
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Whether you’re trying to mingle at a party, network at a professional event, or make a good impression on a date, a good conversation starter can go a long way. It can be tough to come up with something in the moment, so it’s always a good idea to have a few ice breakers in your back pocket. Luckily, we’ve compiled a thorough list of great convo starters for any situation, and we've also included important insights from image consultants and relationship experts. Keep reading for everything you need to know!

Good Conversation Starters

  • How is your day going so far?
  • Do you have any big plans for the weekend?
  • How do you know the host?
  • I love your shirt. Where did you get it?
  • What do you like to do for fun?
  • Have you ever been to this place before?
  • Are you having a fun time?
Section 1 of 6:

Great Conversation Starters for Any Situation

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  1. Image consultant Lynda Jean recommends keeping things general at first and steering clear of heavy topics like politics or religion. Then, once you’ve gotten the conversation going, “Always smile, make good eye contact, and listen more than you talk,” she recommends. Here are some questions to ask, whether you’re meeting someone for the first time at a party, chatting with a new acquaintance, or striking up a convo in line at the grocery store.
    • I love your outfit. Where did you get it from?
    • How has your day been so far?
    • Have you ever been to this place before?
    • Are you from around here?
    • What’s been going on in your life recently?
    • What’s something that made you smile or laugh this week?
    • Has this been a busy week for you?
    • What do you do for work?
    • What do you like to do for fun?
    • How do you like to spend your weekends?
    • Do you have any fun hobbies?
    • Do you have any pets?
    • Are you a dog or a cat person?
    • What brings you to this party?
    • How do you know the host?
    • Do you know a lot of people here?
    • Are you enjoying the party?
    • How have you been doing since the last time I saw you?
    • Have you been watching any good TV shows lately?
    • What’s the best movie you’ve seen so far this year?
    • Are you reading any good books right now?
    • What kind of music are you into?
    • Do you listen to any podcasts?
    • What’s your favorite kind of food?
    • What’s your favorite cocktail or drink? Can I get you one?
    • Are you a coffee or tea person?
    • Do you have any good restaurant recommendations?
    • Do you enjoy cooking?
    • Have you been on any fun vacations recently?
    • What is your favorite place to travel to?
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Section 2 of 6:

Conversation Starters for Dating

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  1. “I would advise [clients] to ask questions about the other person and talk less about themselves,” says expert dating coach and matchmaker Judith Gottesman. In fact, research has shown that asking good questions is a top factor people consider when deciding whether or not to go on a second date with someone. Here are some questions you can use to demonstrate your curiosity and desire to know the other person better: [1]
    • This place looks amazing! Have you ever eaten here before?
    • Are you from around here? Or did you grow up somewhere else?
    • What are your favorite and least favorite things about first dates?
    • What are you looking for in a partner?
    • Do you have any dating deal breakers?
    • What are your biggest pet peeves?
    • Are you looking for something serious, or something more casual?
    • How would you describe your communication style?
    • Do you prefer talking on the phone or texting?
    • What’s your love language?
    • Would you consider yourself a romantic person?
    • What’s your biggest turn-on?
    • What random thing do you find super attractive?
    • Are you more of an introvert or extrovert?
    • What qualities do you want your future spouse to have?
    • What made you interested in going on a date with me?
    • What does the ideal relationship look like to you?
    • If you had to describe yourself in one sentence, what would it be?
    • Have you ever been on a blind date before?
    • What’s the funniest or wackiest dating experience you’ve ever had?
    • When you picture your life in 5 years, what does it look like?
    • Do you believe in astrology? If so, what’s your sign?
    • What gives you butterflies when you’re on a date with someone?
    • When you picture the perfect date night with your future partner, what does it look like?
    • If you had to make a mixtape of your favorite songs ever to give to a potential partner, what songs would be on it?
    • Do you believe in soulmates?
    • Do you believe in love at first sight?
    • What do you think is the most important thing to know about someone before getting into a relationship with them?
Section 3 of 6:

Flirty Conversation Starters for Texting Your Crush

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  1. Oftentimes, you’ll need to break the ice with your crush over text before heading out on a real date, which can be a little nerve-wracking. [2] Luckily, we’ve pulled together a bunch of flirty conversation starters to help you start connecting with your crush!
    • Hey! How has your week been going so far?
    • Are you up to anything fun this weekend?
    • Congrats on your big win at the game today! We should totally celebrate 🎉
    • You did so well on that presentation in class today. You’re gonna get an A for sure!
    • Ugh, that test was so hard. How do you think you did?
    • Just watched the new episode of the show you told me about. It was crazy! Have you seen it yet?
    • The band you told me about just dropped a new album! Did you listen yet?
    • The wildest thing just happened to me. I have to find you before class tomorrow to tell you about it!
    • I’m so bored tonight! What are you up to?
    • I’m craving ice cream from that place you were talking about. Do you want to go grab some?
    • I can’t stop thinking about you 💕
    • Just wanted to say you looked super cute when I saw you today 😍
    • Forgot to tell you when I saw you, but I love your new haircut. It looks great on you 😘
    • I had fun hanging with you today! We should definitely do it again soon
    • This new movie that’s coming out looks so good! We should go see it
    • Send them a song, photo, meme, or article they would like, and text something like: This made me think of you 😊
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Section 4 of 6:

Funny Conversation Starters

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  1. Everyone loves to laugh! In fact, laughter is known to relieve stress, elevate mood, and improve relationships. [3] Plus, a great sense of humor can make you appear more confident and trustworthy, while also diffusing tension or awkwardness in any given situation. [4] Here are some funny conversation starters to break the ice with new people, or pass the time when hanging out with friends:
    • What is the worst pickup line you’ve ever heard?
    • What’s the most embarrassing fashion trend you ever took part in?
    • Which current fashion trends do you think people will be super embarrassed of in the future?
    • What do you think is the worst fashion faux pas someone can make?
    • What’s your go-to karaoke song?
    • Do you ever sing in the shower?
    • When was the last time you laughed so hard that you cried?
    • What is the weirdest food combination that you swear by?
    • What is the best dipping sauce to dip fries in?
    • What are the most overrated and underrated fast food restaurants in your opinion?
    • What’s your favorite late-night snack?
    • What’s the grossest thing you’ve ever eaten?
    • Do you have any controversial hot takes about a movie or TV show?
    • What’s the funniest movie scene you’ve ever seen?
    • If you could trade lives with a famous person, who would you pick?
    • Do you have any guilty pleasures?
    • Do you have any strange or quirky hidden talents?
    • What is the worst joke you’ve ever heard? And the best?
    • Did you enjoy playing pranks on people as a kid?
    • Who is your favorite stand-up comedian?
    • How would you describe your sense of humor?
    • Do you believe in any wacky conspiracy theories?
    • Do you believe in aliens?
    • What celebrity would play you in a biopic about your life?
    • If there was a national holiday honoring you, how would you want people to celebrate it?
    • What is the most awkward moment you’ve ever experienced?
    • What’s the most embarrassing question in your Google search history?
    • What never fails to make you laugh, even when you’re upset?
    • Would you rather be able to read people’s thoughts or teleport to anywhere in the world?
    • If you could erase one song from human history so that you’d never have to hear it again, which song would you pick?
Section 5 of 6:

Deep Conversation Starters For Couples or Friends

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  1. These conversations allow you to learn about the other person on a more intimate level, which can truly strengthen your bond. [5] If you’re not sure how to get a deep convo going on your own, have no fear! We’ve compiled some great questions to help you move past small talk and connect in a more meaningful way.
    • What is your number one goal in life?
    • What is the accomplishment you’re most proud of?
    • What is one personality trait you have that you’re especially proud of?
    • What do you think people would be surprised to learn about you?
    • What was your dream career when you were a kid? Did it change as you grew up?
    • What is your favorite childhood memory?
    • Who is your biggest role model and why?
    • If you had to condense your worldview into one personal motto, what would it be?
    • Who is the most important person to you at this moment in time?
    • Which of your immediate family members are you closest to?
    • What are you most afraid of?
    • What’s the biggest challenge you’ve had to overcome?
    • If you could go back in time, would you do anything differently in your life?
    • If you could talk to your 16 year old self, what advice would you give?
    • Is there something in your life you really want to change?
    • When are you happiest?
    • Where in the world do you feel most safe?
    • Do you have any strong opinions that have changed over time?
    • What inspires you creatively?
    • What are you most passionate about?
    • What do you think is the best book ever written?
    • Who is your favorite musical artist, and why do you resonate with them?
    • If you could pick a historical figure to have dinner with, who would you choose?
    • If you wrote a memoir, what personal stories would you make sure to include?
    • Do you think people are fundamentally good at heart?
    • What do you think makes someone a good friend?
    • Do you believe in the supernatural, or do you only believe in material reality?
    • What do you think happens after death?
    • What’s a secret you’ve never told anyone?
    • How are you actually doing? Are you going through anything difficult right now?
    • What’s something you wish people knew about you?
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Section 6 of 6:

Conversation Starters for Networking

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  1. And, like any other skill, preparation and practice are key! Licensed clinical psychologist Dr. Donna Novak recommends memorizing a few go-to conversation starters beforehand, so that you have them in your back pocket when you’re at the event. “Having some ideas of the actual language you’re going to use is really helpful for that anxiety,” she says. Here are a few professional conversation starters to inspire you:
    • What brings you to this event today?
    • This is my first time at this kind of event. Have you been to one before?
    • Are you from around here, or did you travel from far away?
    • The food is delicious. Have you tried it yet?
    • Did you enjoy the speaker/presenter?
    • What made you choose this career?
    • How did you break into the industry you’re working in?
    • I’m hoping to make a career change into your line of work. Do you have any advice?
    • How long have you been at your current company?
    • What’s your favorite thing about your job?
    • What do you think is the most valuable skill to have in your industry?
    • What are your professional goals this year?
    • Who has been the most influential professional mentor in your life?
    • Do you ever travel for work? If so, what’s your favorite destination?
    • Have you faced any big challenges at work recently?
    • Are you working on any cool projects?
    • What are your favorite productivity tips?
    • Do you prefer remote work or going into the office?
    • Have you ever tried a standing desk, or do you prefer a traditional desk?
    • What’s the best professional advice you’ve ever received?
    • Where did you go to school? Did you enjoy your time there?
    • Which teacher or professor had the biggest influence on your career path?
    • What was your first job? Did you enjoy it?
    • If you could have a completely different job for the day, what would you choose?
    • If you weren’t working in your current field, what do you think you’d be doing?
    • If you could change one thing about the industry you work in, what would it be?
    • What do you think makes someone a good boss or manager?
    • Do you enjoy these types of networking events?
    • I really enjoyed talking with you! Would you be open to connecting on LinkedIn?
    • I’d love to chat with you more sometime! Do you have a business card? [6]

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      References

      1. ↑ https://www.psychologytoday.com/us/blog/joyful-parenting/202401/what-science-says-about-asking-questions-on-a-date
      2. ↑ https://www.thecut.com/article/how-to-flirt-over-text-tips-and-flirty-texts-examples.html
      3. ↑ https://www.helpguide.org/articles/relationships-communication/managing-conflicts-with-humor.htm
      4. ↑ https://www.gsb.stanford.edu/insights/make-em-laugh-how-humor-can-be-secret-weapon-your-communication
      5. ↑ https://psychcentral.com/health/deep-conversation-starters
      6. ↑ https://www.brandeis.edu/hiatt/connections/network-interview/conversation-starters.html

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