“How are you?” might be one of the most common conversation starters we use and one of the least likely to get an honest answer. Most of us respond automatically: “Good.” “Fine.” “Not bad.” Then we move on. It’s less of a question than a social reflex.
But if you actually want to know how someone is doing, try asking something they haven’t answered a thousand times before. A slightly different question can lead to a completely different conversation, whether you’re talking with a friend, partner, family member, coworker, or someone you’re just getting to know. Here are 25 things to ask instead of “How are you?” that might get you past “I’m fine” and into a conversation that actually means something.
25 Conversation Starters
1. How have you been, really?
2. How is your day?
3. What’s been going on with you lately?
4. How’s life treating you?
5. What’s new in your world?
6. How are things going these days?
7. What’s been on your mind lately?
8. What’s been the best part of your week?
9. What’s been keeping you busy these days?
10. What are you looking forward to right now?
11. What’s making you happy lately?
12. How are things going outside of work?
13. What would you be doing if you didn’t have to work today?
14. What’s something good that happened recently?
15. What’s been challenging you lately?
16. What are you excited about these days?
17. What’s taking up the most space in your head right now?
18. What’s something you wish you had more time for?
19. What’s been giving you energy lately?
20. What’s been draining your energy lately?
21. What’s one thing you wish people would ask you about?
22. What’s something going on in your life that you haven’t had a chance to talk about?
23. What happened with [bring up something you had a conversation about recently, e.g., the dinner party they were planning, the puppy they were thinking about getting, etc.]?
24. How is your [family member] doing?
25. Offer a sincere compliment!
Bonus Section: Conversation Starters with Your Manager
For a boss, keep them warm and personable without getting too personal:
1. How’s your week going so far?
2. What’s been keeping you busiest lately?
3. Is there anything you’re looking forward to this week?
4. Has it been a pretty manageable week, or one of those weeks?
5. What’s been the highlight of your week so far?
These work because they give your boss something specific to respond to without putting them in the awkward position of having to disclose anything personal.
Bonus Section: Conversation Starters for Someone You’re Just Getting to Know (Including First Date Questions!)
1. What’s something you could talk about for hours?
2. What does your perfect weekend look like?
3. What’s something you’re looking forward to right now?
4. What’s something people are usually surprised to learn about you?
5. What have you been really into lately?
These stay light enough for a newer relationship but give the other person room to share something more interesting than the usual job, weather, and weekend small talk.
Bonus Section: Conversation Starters for People Who Hate Small Talk (or When You Don’t Know What to Say)
1. Do you have anything fun coming up?
2. What do you usually do when you have free time?
3. What is a challenge or obstacle you’re facing now?
4. Have you hear of [something interesting you recently learned about]?
5. What do you usually say when someone asks for a “fun fact” about you?
Do you have any great conversation starters? Maybe something you say to people in elevators or to your in-laws? Write it in a comment!