7 Questions to Ask on a First Date That Are Guaranteed to Get the Conversation Flowing

Not too shallow and not too deep, these prompts can help you get to know one another while (mostly) avoiding awkwardness.

Let's face it: When you're not actively engaging with people face-to-face, it can feel tough to remember exactly how to make small talk and have meaningful conversations. And that's to say nothing of dating, which has been turned upside down by the digital age. If you're thinking about dating again—and we mean in real life, actually-meeting-the-person kind of dating—you might find yourself needing a playbook. If you're asking questions— like "What should I say?" or "What should I ask?" or "What topics should I not bring up?"—we're here to help, even providing suggestions for what to do when a first date gets awkward, and how to determine whether you should go on a second date.

First Dates Are Inherently Awkward—Here's Why

Why do first dates feel so weird, anyway? Christie Kederian, Ph.D., psychologist and licensed marriage and family therapist, says it has a lot to do with the wide range of thoughts racing through our minds. "On a first date, there's a lot that's happening psychologically," she says. "You're having to juggle multiple layers in your mind."

The first layer is reconciling that you're going out to spend time with someone you previously may have never laid eyes on. "From a young age we're told, 'don't talk to strangers,'" Kederian says. Second, you're trying to assess for compatibility—i.e., do you feel a connection with this person? And the third layer is chemistry. Do you get along well? Do you enjoy talking with them? If you're a little out of practice with social environments, then that adds yet another layer. For instance, you may wonder: Should I hug them, shake their hand, or avoid physical contact altogether?

It's a lot to think about at once, and there are consequences—namely, the feeling that it's all pretty weird. "What happens when you're thinking more and in your head is that you're not present in the moment," says Kederian. "That's what leads to that awkwardness." The good news, though, is that you can avoid it with a little prep work.

First Date Questions and Conversation Starters

"When you're face to face, it's important to have elements of both lightheartedness, but also try to go a bit deeper and learn more about them as a person," says Kederian. Avoid being too superficial or going too deep with first date questions and prompts like these:

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"What's a fun memory from your childhood?" or "How would you describe yourself as a kid?"

These are light conversation starters that might help to bring up a funny story while also revealing a bit about who they are and their upbringing, says Kederian.

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"Where's your happy place?"

Asking this helps you get to know about what they're interested in, a hobby of theirs, and what feeds them as a person, she adds.

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"Tell me about your job. How did you get into it?"

This question allows you to dive into a person's professional passions, says matchmaker Rori Sassoon, relationship expert for the UnFiltered dating app. "Working is a big part of a person's daily life," she adds. Talking about their career can provide some insight into whether they're more analytical or creative. Plus, "if the conversation hits a slump, you can always bring the chat back to the 9-to-5," Sassoon says.

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"What's a typical Saturday for you?"

This one may go in any direction, but in general, it will likely provide a space for you to talk about hobbies and interests, along with giving you a picture of their ideal weekend, says Sassoon. If you discover you enjoy similar activities, that can also provide future date ideas.

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"Describe your personality in an ice cream flavor."

Getting creative and silly is the point of this conversation starter, but it also enables the person to reveal more about who they are—a terrific segue toward a deeper chat, says Sassoon. Don't be surprised if this question also leads to some good laughs.

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"We have 24 hours to plan a trip. How are we packing our bags?"

This is a great question to learn what each person finds intriguing in a potential getaway, says Sassoon, and can help determine compatibility. For example, are they more of an outdoorsy person, or do they love a cityscape? Do they prefer a go-go-go pace for sightseeing, or prefer to chill out on a beach? Asking about travel also opens the door to more conversation—maybe you've been to their favorite place or have always wanted to visit, enabling you to continue the dialogue.

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"What's your go-to karaoke song and why?"

This is another question that can reveal a lot about someone's personality without going too deep. "A shared love for music is a great way to propel the conversation forward and establish compatibility," says Kate MacLean, resident dating expert with Plenty of Fish. "Karaoke taps into nostalgia and provides an opportunity for both of you to share fun memories and can open the door to other music-adjacent conversations like 'What's your favorite band?' or 'Who's the best musical artist of each decade?'"

Avoid Going Too Deep

Keep anything too serious off the table on a first date, says Kederian. This includes topics like past relationships, whether they'd like children, and what they want out of life. "Try to keep things focused on whether you have chemistry," she adds. "This is a time to see if you have that connection." (Save those intimate and meaningful questions to ask later on, if you enter into a relationship.)

Safe Strategies if a First Date Gets Awkward

If you do hit a moment during your date when neither one of you knows what to say next, it doesn't necessarily spell doom. "As long as a first date doesn't completely bomb, I would definitely give it a second date," says Kederian. "Most couples don't come out of a first date saying, 'Oh, this was the one.'"

There are simple ways to move beyond any uncomfortable silence, though. Try to ask a question that enables you to find a show or a book that you both enjoyed, and you'll have something to talk about, says MacLean. For example, you could say, "I've watched so many good shows lately—what's your most re-watched/favorite one?" or "I've read so many great books over the last year—what's your favorite book?" Alternatively, you can fall back on asking about other activities they may have done recently, like baking or listening to podcasts.

Pets are another positive, easy topic that often enables you to find common ground, says MacLean. More than 60 percent of singles said four-legged friends were the best icebreaker when it comes to meeting someone, according to an August survey of 3,400 Plenty of Fish users.

Additionally, commenting on your surroundings and what's happening where you are in the present moment is always a good fallback topic, as it's already a shared experience for the two of you, says Kederian.

First Date Dos and Don'ts

Don't come in too hot with jokes.

While it may seem tempting to come up with a charming opening or even make a joke as an opening line when meeting someone in person for a first date, Kederian says it's better to just be yourself. "I don't recommend doing anything like that, as it could go any which way," she says. "You don't know how people will perceive it." A good rule of thumb is to keep things lighthearted without assuming too much about a person's sense of humor ahead of time.

Keep it shorter than you think.

Plan for a first date to not last too long. Kederian suggests keeping your time together from one to one and a half hours, like meeting up at a café for dessert and coffee or at a restaurant bar for wine and cheese. Also, consider planning something you need to do after the date ends so you have a clear stopping point. "The pressure happens when you plan a first date that ends up going for three hours," she adds, which can open the door to awkward silences.

Don't look at your phone.

Remember to give your connection a chance by keeping your phone off the table (and not checking it every five minutes). "Try to stay focused, keep eye contact, and don't look around at every person walking by," says Kederian.

End on a positive note.

Finally, if you enjoyed getting together, be sure to express that before you head on your way. It can be as easy as saying, "Hey, I had fun meeting you, and would love to do it again sometime." This opens the door to a second date and leaves the ball in the other person's court, says Kederian. She recommends doing this even if you aren't positive you had a strong connection. Relationships need time to unfold, so do some reflecting after your first date is over to assess how it went. "You might be surprised after the date [to realize] that you had a good time, [because] when on the date, you might have been too nervous," she says. "Suspend judgment and don't decide while you're on the first date if you want a second one."

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