Whether you’ve known someone for 10 minutes or 10 years, there are always new things to discover about them. Coming up with fun, interesting questions on the spot can be tough—which is why we’ve compiled a list for you! Try asking these at the next party or get-together you go to for an interesting conversation that’s sure to engage everyone.

Method 8
Method 8 of 11:
“If you could be any celebrity, who would it be?”

Method 11
Method 11 of 11:
“What movie absolutely scarred you for life?”

Community Q&A

  • Question
    What kind of questions should I ask my crush?
    Maria Avgitidis
    Maria Avgitidis
    Matchmaker & Dating Expert
    Maria Avgitidis is the CEO & Matchmaker of Agape Match, a matchmaking service based out of New York City. For over a decade, she has successfully combined four generations of family matchmaking tradition with modern relationship psychology and search techniques to ensure her professional clientele are introduced to their ultimate match. Maria and Agape Match have been featured in The New York Times, The Financial Times, Fast Company, CNN, Esquire, Elle, Reuters, Vice, and Thrillist.
    Maria Avgitidis
    Matchmaker & Dating Expert
    Expert Answer
    Let the conversation flow organically. Ask questions about their plans for the upcoming weekend and what their lifestyle and values are. It's important that you emphasize having fun and letting the conversation flow naturally.

About This Article

Hannah Madden
Co-authored by:
wikiHow Staff Writer
This article was co-authored by wikiHow staff writer, Hannah Madden. Hannah Madden is a writer, editor, and artist currently living in Portland, Oregon. In 2018, she graduated from Portland State University with a B.S. in Environmental Studies. Hannah enjoys writing articles about conservation, sustainability, and eco-friendly products. When she isn’t writing, you can find Hannah working on hand embroidery projects and listening to music. This article has been viewed 15,281 times.
33 votes - 79%
Co-authors: 6
Updated: August 25, 2021
Views: 15,281
Categories: Conversation Skills