Couple sitting at bar and looking irritated

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Making conversation on the first date is hard. I get it. But there’s one question I despise— yes, more than lingering silence— when I’m sitting across a bar, table, or even looking at my smartphone screen. And that is: “Why are you single?” No answer is a win here. Almost every response puts you in one of two boxes. To some folks, you’re either angry and lonely or you’re hoe-ing it up. Even the popular response, “I haven’t found the right guy/girl yet,” can come across as cliché, corny and unbelievable. And let’s not forget the other unintended outcome: It makes you start thinking about the one who got away, or brings up negative feelings from past relationships. There’s gotta be a better way.

With summer dating season approaching, I  decided to ask my friends, IRL and via social media,  what they preferred to be asked on first dates. There was no shortage of responses, and one thing became clear: successful first dates aren’t about whether there will be a second date or whether you got it in. It’s more about creating a vibe. Did the conversation flow? Were you laughing? Did you get deep? Did you get anything out of this moment?  With that in mind, I created a best of the best list, filled with questions that are musts, whether you want to land a second date or a potential causal sex buddy, but don’t want to sound like you’re in a rapid-fire interview.

1 Do You Like What You Do?

No one is more miserable than a person who feels stuck, unfulfilled or lost professionally. Whether you want to just kick it or are looking for something that can turn into more, good vibes and energy are everything.



What Podcasts Do You Listen To?

This question allows you to learn more about the person’s interests, whether you’ll have natural vibe and connection, and, most important, where she/he stands on potentially important stuff. If the individual isn’t listening to any podcasts (it happens), share your favorites and find out whether it piques any genuine interest.

3 What Would Make This An Amazing Night?

Preface this taking sex and anything that has to do with spending a crazy amount of money off the table. This question is a great one to find out more about what makes a person feel more connected to others. It’s also a cool way to have the most fun possible with an individual without being focused on whether you’re getting something “right.” Once you know, you can decide whether or not you want to do “that thing,” then stay in the moment.

4 Where Did You Grow Up?

Don’t make this invasive or creepy. Offer a little bit about how you grew up and then toss the question back. Sibling order, socio-economic status, neighborhood/city/state and parental situation all shape a person. It also gives you a natural in to see what experiences you have in common, what you can learn from each other and set expectations. 

5 Favorite Vacation?

This tells you whether the person values exploration, relaxing and adventure. It also gives you a glimpse into what your experiences with the individual will be like. For example, is this a person who’s vacationing regularly? Is this a person who thinks spending money on an experience is whack? The goal here is to talk about how this individual wants to live.

6 Which Political Issue Is Most Important to You Right Now?

This may seem like a lot for the first date, but you want to know whether someone has a stance on a big issue that varies greatly from yours.

7 What Are You Looking For?

This is a must.  It’s a great way to gain clarity up front and avoids any unfair and awkward expectations. Ask this closer to the end, so you can get to know the person and create a rapport without being biased based on their intentions.


Chelsea Hamlet is a freelancer for CASSIUS.