Protect yourself! If you think you’ve been targeted by a scam, click here to get information and assistance from the AARP Fraud Watch Network Helpline!
Sisters Site Logo.svg
Oh no!
It looks like you aren't logged in to the Sisters community. Log in to get the best user experience, save your favorite articles and quotes, and follow our authors.
Don't have an Online Account? Subscribe here

40 More Ways to Chat Up Anyone

We’re back with a new list of conversation starters that may help you break the ice and build friendships.

Comment Icon
3 women having a laugh outside at a coffee shop
Getty Images
Comment Icon

Lately, I’ve been challenging myself to talk to more people. Although I’m an introvert and love flying solo, I know that maintaining a healthy social network has advantages: It can increase our sense of happiness, help us stay healthier — physically and mentally — and may even help us live longer.

I want to reap all of those benefits. Hence, my “talk to people” goal. Problem is, I’ve never been big on starting conversations. I get nervous and flustered, and have no idea what to say in certain situations.

Nicole Murray, Psy.D., a neuropsychologist at New York Neurobehavioral Services, works with clients to help improve their emotional intelligence. She says for someone who feels uncomfortable talking to new people or initiating conversations, "having questions prepared in advance is a form of mental rehearsal and can take the anxiety out of interactions.”

A few tips before you start:

  • Read the room. If someone seems uninterested or is short with their responses, don’t try to force a conversation.
  • Be positive. “People tend to gravitate toward positivity and shut down when negativity is introduced,” Dr. Murray says. “So, instead of saying, ‘The bartender is so slow,’ you could say, ‘I love the drinks here. What do you like to drink?’ ”
  • Think beyond one question. It’s always good to have a follow-up question in mind to keep the conversation going, Dr. Murray says. For example, say you ask, “What brings you to this event today?” She recommends responding to the person’s answer with something like, “Me too! What’s been your favorite aspect so far?”

To come up with some great conversation starters, I turned to several sources for inspiration: Dr. Murray; the books 4,000 Questions for Getting to Know Anyone and Everyone, by Barbara Ann Kipfer, and 101 Conversation Starters for Families and 101 Conversation Starters for Couples, by Gary Chapman, Ph.D. (author of The 5 Love Languages); and TableTopics, a card collection of questions to kick off interesting, fun and meaningful discussions.

These questions have helped me (and can help you) spark a good conversation anywhere: at networking events, happy hour, work, a first date or a 50th date; while hanging with family or friends; or when meeting someone new.

  • Have you attended any other events like this before? If so, are there any that you recommend?
  • I hear you’re from [wherever]. What do you like about your hometown?
  • Which song always cheers you up?
  • What happened on your best day this week?
  • Your hair looks amazing! Any tips you can share to help me get mine as luscious as yours?
  • What talent do you wish you had?
  • What industry do you work in, and what led you to pursue that career path?
  • Are you from around here? If not, what brings you to this area?
  • What dessert could you eat forever?
  • What’s something you did to try to impress me when we first started dating?
  • Do you prefer to relax and do nothing on vacation or do all the activities?
  • Have you tried any new restaurants or bars in the area recently that you’d recommend?
  • What’s your favorite type of exercise?
  • How do you like to unwind after a long day or week at work?
  • What product do you like so much that you could become a spokesperson for it?
  • What’s something you really wanted but weren’t allowed to own as a kid? Did you ever get it when you got older?
  • Which one of your mom’s crazy rules do you still follow?
  • When was the last time you danced until you were a sweaty mess?
  • Would you prefer we had one season the whole year? Which one?
  • What are some amazing books or podcasts that have helped you learn about your industry?
  • What TV commercial has worked on you? What did it convince you to purchase or try?
  • If you could hang out with a celebrity for an hour, who would you choose?
  • What movie have you seen so many times you can quote it?
  • Your dog is so cute! What do you like most about that breed?
  • If you were a superhero, what power would you possess?
  • If you had a time machine and could travel to the future, which year would you go to? Why?
  • That book looks interesting! Do you mind telling me the plot?
  • Which celebrity chef would you choose to fix you breakfast?
  • What made you interested in going out with me tonight?
  • If you had an extra hour every day to do something for yourself only, how would you spend that time?
  • What’s a hobby you enjoyed as a child but haven’t done in years?
  • Your shirt/tattoo caught my attention. Is there a story behind it?
  • What 1980s fashion trend can you still not believe you followed?
  • What’s one question you would love to be asked on a first date?
  • What was your favorite birthday?
  • How did you get into doing [fill in the blank]?
  • What’s a perfect Friday night like for you?
  • Which would you choose to be: 20 percent richer or 20 percent happier?
  • Which hobby of yours do you think would make a good career?
  • What’s something about you that surprises people?
Follow Article Topics: We-Time