First Date Questions to Get to Know Your Match Better

Going on a first date is equally exciting and anxiety-inducing. We all dream of hitting it off with our matches instantly. But the thing is, it rarely happens.

Fortunately, no one is doomed to have awkward dates forever. But for that, you may need a roadmap for comfort. This means planning your first date questions, from the timing and manner of asking.

This is where our guide comes in handy. We’ve compiled a list of questions that’ll lead to meaningful conversations. We bet these will give you insightful answers from your match.

What Should Your First Date Questions Accomplish?

Before you look for what to ask on a first date, let’s discuss why your questions are important.

First dates are a big deal for a reason. They don’t predict how relationships will go, but they do set the stage for their beginnings. Your questions should check these boxes so you’ll have a clear direction:

They should help assess and build potential connections

Questions indicate curiosity, which helps people gain more knowledge about each other. If this curiosity keeps up, there’ll be more conversations. You’ll be building connections before you know it.

They should help determine compatibility or incompatibility

As mentioned, curiosity helps build connections. As that connection grows, you’ll see a person’s everything—the good, the bad, and the ugly. Questions tell you whether you and your match will be compatible in the long run.

How Should You Ask Your Questions?

There’s a proper way to go about asking your questions. These tips should help you in the delivery department:

#1: Don’t sound like a recruiter during a job interview.

The last thing you want is to add to the intimidating atmosphere of your first date. You’re not an HR employee, and your match isn’t a candidate or applicant.

If you have a long list of questions, pick the relevant ones and weave them naturally into your conversation. Remember to use casual and friendly language.

#2: Switch gears if you’re stuck.

Sometimes, conversations don’t flow as smoothly as you’d like. And that’s normal!

When this happens, you can always bring up another subject through another question. You can say something like, “Can I ask something?” or “I have a question” to make that transition.

#3: Respond to “what about you” follow-ups.

Your date wants to know about you, too. We’re sure they have just as many questions as you do. So when they turn the tables and ask you something as a follow-up, don’t leave them hanging.

Great First Date Questions to Ask

At this point, you’ve already understood why questions on first dates are necessary. And with that, let’s finally get to the questions themselves.

The Basics

Let’s scratch the surface first before getting deep. Icebreakers exist and are asked first for a reason. They ease tension and make dates more comfortable.

The answers to these questions may seem basic. But they clue you in on your match’s preferences that you may want to remember or bring up later.

Start on the right note with these introductory questions:

• What do you like to listen to?
• What does your typical weekend look like?
• Are you an indoor or outdoor person?
• How do you usually spend your downtime?
• Are you a dog or cat person?

Values

We get that you want sizzling hot chemistry off the bat. However, compatibility is just as important. The vibes may be good, but they don’t tell you if you and your match fit together in the long run.

This is why getting attached to them early on can be disastrous, especially if they're a stranger. Your feelings may make you miss otherwise obvious red flags.

Compatibility takes time to gauge, but these questions may give you a peek at what’s to come:

• What do you value most in relationships?
• How are you with your family?
• What do friendships mean to you?
• Who makes up your support system?
• How do you pull off work-life balance?

History

This category can get tricky. Sure, you want to know what you can about a match’s romantic history. However, the questions may hit a few nerves. We recommend asking these when you’ve read the room and 100% eased the tension:

• How many serious relationships have you been in?
• How long was your longest relationship?
• What do you want out of a relationship?
• Why and how did your last relationship end?
• Should exes stay friends? Why or why not?

Communication Habits

We can’t overstate the importance of communication enough. It’s among the building blocks for healthy relationships. And this isn’t limited to your choice of words. How you say them matters, too.

If you want to know your match’s communication style or tendencies, these questions should give you a clue:

• Do you prefer texting or calling?
• How do you express your love?
• How would you like your partner to express their love?
• Do you speak up when something’s bothering you?
• Who do you think should take the lead in a relationship?

Intentions

Some understandably get cold feet when asking the “what do you want” type of questions. But if they aren’t raised, intentions will remain unknown.

Here are things to ask on a first date to spare yourself the anxiety:

• What’s your dating style like?
• What are your non-negotiables?
• What’s your take on commitment?
• What are you looking for, relationship-wise?
• How long do you wait until you attach a label to a connection?

Deep First Date Questions

After reading the subhead, some of you may think it's too early to ask these. But if you already have the first four categories down, these are appropriate questions.

For example, you’ve known each other for a while and transitioned from friends to potential lovers. Asking these questions can make that adjustment easier:

• What else don’t I know about you?
• What are your relationship goals?
• How do you want to be supported?
• What can I do to make you feel safe?

We hope these first date questions will help you build your desired connection. You know what they say; you won’t know until you ask.

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