50 Non-Awkward Questions for a First Date That’ll Actually Spark a Connection

Meeting a potential partner should be exciting, but the nerves and pressure can easily make things…uncomfortable and intimidating. That’s where prepping a few questions for a first date can come in handy: A good one will prevent much-dreaded silence and maybe even spark some real chemistry.

“We ideally want conversations to flow organically,” Payal Patel, LMFT, licensed therapist and CEO of Manu Counseling in Montclair, New Jersey, tells SELF. But let’s be honest: You’re with a person you don’t know in an unfamiliar yet intimate setting, and the stress can be intense—especially when you’re worried about making a solid first impression or anticipating yet another dating horror story. Awkward silences are bound to happen, but Patel says the right icebreaker can ease some of that initial tension—and in a perfect world, eventually lead to smooth, engaging chats that feel organic, not scripted.

The trick, though, is striking the right balance: You want it to be a genuine exchange, not a pre-planned job interview. What makes a “great” conversation starter depends on your dynamic—something Patel says you’ll likely have to feel out as the date unfolds. For example, “some couples are open to deep and intimate questions about their past relationships or future together, while others aren’t comfortable with those types of discussions so early on,” she explains. Not to mention, asking about marriage right off the bat might be a bit much for a person who’s just looking to have a good time.

So if you’re hoping to skip the cliché small talk (Where do you live? What do you do for work? Tell me your life story) and actually build a real connection, here are a few expert-approved options to help you break the ice—and see if there’s potential for a second date.

First, what makes a “good” conversation starter?

No matter the topic, what’s important is that your conversation starters actually, well, lead to conversations. For that reason, Rachel Zar, PhD, LMFT, AASECT-certified sex therapist at Avid Intimacy in Chicago, tells SELF that it’s best to stick with open-ended questions that’ll invite more than just a one-word response. Instead of saying, “Do you want kids?” for instance, try, “How do you feel about having kids?” The latter opens the door to a real discussion rather than a potential dead end.

It also helps to lean into things you know they’re into, Dr. Zar adds. Depending on how you connected, you probably already have a little background like the job they’ve had for five years, say, or their pets all over their dating profile. “People love talking about themselves, and they’ll light up when you mention things they’re passionate about,” she says.

However, conversations are a two-way street—meaning, even if you come up with the most thought-provoking questions, it doesn’t mean much if you’re not actively contributing. Chances are, they’ll probably ask a few predictable basics—how your day was, what your hobbies include, etc. In that case, Dr. Zar says “it can take the edge off to have a story or two ready about something that happened to you this week, or a personal interest you’re excited to talk about.” That way, you’re not left drawing a blank and adding to any awkward vibes.