Conversation Starters for a First Date

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First dates can be stressful, but they don’t have to be. There’s so much pressure to make sure everything is perfect- perfect outfit, perfect place, perfect meal… but arguably the most important piece that separates a great date from a bad one isn’t your shoes, but how well the conversation flowed. After you’ve let your date know that you’re meeting at either Kelsey’s or Boston Pizza on Clifton Hill at 6:00 p.m you might be wondering, now what? What else can I do to prepare for this date and make it something special?

Having a loose idea of topics (or even specific questions depending on how nervous you are), can make you feel more at ease walking into your date. Be careful though- you’ll want to stay as natural as possible, so we definitely don’t recommend you pull out a list of pre-planned questions out of your pocket. Instead, practice asking them aloud or even to the mirror. Just as important as asking thoughtful and provoking questions though is being attentive enough o actually hear the answers. Be careful not to get so lost in your plan of asking good questions that you forget to listen! We’ve compiled a list of the most interesting questions and conversation starters that you can use if you and your date need a little help. And remember, have fun!

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Conversation Starters

“What’s something that I wouldn’t guess about you?”

Asking your date this question lets them know that you’re curious to really know them, beyond what you can see and tell from the surface. It’s just the right amount of flirty without being too obvious (which can kill the vibe on a first date). It also isn’t too forward, you’re not directly asking them to reveal to you their darkest secrets, but instead, are leaving it open for them to decide what to and what not to share.

“If you didn’t have to worry about work or money, what would you spend your days doing?”

This inquiry can really brighten someone up- who doesn’t like to gush about their dreams and fantasies?! The answer can tell you a lot about a person like what their values are, what they are passionate about, and what kind of lifestyle they would like to live. But at the same time, it doesn’t feel invasive and can be quite a light and fun conversation to have. It’s also a great way to tell how compatible you are. If their answer would be to spend every waking hour outside in nature and you avoid trees and grass like the plague, this can be quite useful to know!

“What has been the most significant or life-changing year of your life?”

Of the rest on this list, this question has the potential to be the deepest. It is extremely reflective and thought-provoking and may have your date thinking for a moment (which isn’t a bad thing, silence is not the enemy!) You get to discover a little bit of their backstory as well as what they consider to be meaningful and important. There are so many opportunities here to ask more questions. If they bring something up that interests you, it could very well lead into its own story or conversation.

Talking Games to Play on a First Date

To get to know one another in a way that’s super fun and light, why not try a few at the table talking games?

You can play two truths a lie, where each of you makes three statements- two that are true and what that is false and try to guess which is which. You can take turns closing your eyes and listing off physical characteristics about your date or list different items they are wearing. You can look around at the other couples or friends and families sitting at the restaurant and guess what they are talking about. The options are endless! With these tips, you’re sure to have a lively night and really get to know your date.

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