conversation tips

Knowing how to start a conversation in a new social or professional setting can be difficult. Small talk can quickly become dull and uncomfortable.

Whether you're returning to work in the office or trying to make new friends in a new city, it can help to have a few conversation starters prepared. The key to engaging people is to start with open-ended questions.

"The best format for conversation starters is to use an open-ended question that allows the other person to speak openly and freely in a casual and comfortable way," Amy Arias, M.A., senior lecturer of communications studies at the University of Nevada, Reno, tells Upworthy.

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Looking for unique conversation starters that will draw people in? Here are 10 questions to get the conversation going:

"What’s giving you energy right now?"

"This question prompts people to move from surface-level small talk to a genuine connection," leadership strategist and executive coach Stacy McCracken, founder & CEO of Impact and Lead, tells Upworthy. "It invites the other person to share. It’s present, personal, and lets you see what’s fueling them—whether that’s a project, a person, or a long-overdue break. It works because it’s about emotion, not status."

"What's the story behind your name?"

"This one usually gets people immediately to connect and share," public speaking expert LaQuita Cleare, founder & CEO at Clear Communication Academy, tells Upworthy. "It allows you to learn a little bit more about the person, the family, and the culture. It's a quick and meaningful way for people to let their guards down and simply tell you a story."

"What’s something your younger self would be proud you’re doing now?"

"I personally love this question, and even ask it to my clients all the time," Cheryl Groskopf, LMFT, LPCC, an anxiety, trauma, and attachment therapist in Los Angeles, tells Upworthy. "This kind of question lights up the inner child and the present-day self, which makes it emotionally rich. It also tends to lead into the stuff people don’t usually talk about first: healing, change, confidence, effort."

"What’s something fun (show, hobby, or place you discovered) that you’ve been enjoying lately?"

"This open-ended question gives people multiple ways to connect (entertainment, activities, experiences), making it easy and low-pressure to engage," Arias notes. "It also naturally leads to follow-up questions and shared stories."

"If you could plan your perfect weekend, what would it look like?"

"It invites the person to share personal preferences and values (adventure vs. relaxation, social vs. solo time) while keeping the tone warm and imaginative," Arias explains. "It encourages playful conversation and creates space for finding compatibility and shared interests. It's worth noting that an effective conversation starter in a romantic context is often not, in nature, romantic."

"What's your favorite place to spend your downtime?"

"This tells you a lot about a person and is a nice intro question that does not pry too much," Cleare shares. "This is also a great one to find common ground, which is what you want to keep the conversation going."

"What’s something that’s caught your curiosity lately?"

"I love this one because curiosity is the spark of every great conversation," adds McCracken. "It opens space for people to share what’s lighting them up—a topic, a hobby, or even a random fact. Curiosity connects people faster than credentials ever will."

"What’s something you wish more people asked you about?"

"Everyone has a part of their life they love but no one ever brings up, like a weird skill, a quiet win, a topic they never get to share," Groskopf shares. "This question lets people steer the conversation toward something that ACTUALLY excites them. It’s casual, but opens a door you normally wouldn’t walk through."

"What do you love about your job?"

"This one is always fun because if they love their job, their eyes light up and they start telling your stories and if they hate their job, that also brings a fun moment and an eye roll," says Cleare.

"What’s surprised you lately?"

"This one always brings out thoughtful, funny, or even vulnerable stories," McCracken says. "It nudges people to reflect—and reflection is where real connection happens. It’s the perfect balance of light and meaningful."