First Date Questions to Help You Hold a Conversation

Ease the tension with our curated first date questions.

Few things are as exciting and nerve-wracking as going on a first date. Some immediately hit it off with their matches. Meanwhile, others feel it’s an impossible mountain to climb.

One of their reasons? They fail to sustain conversations. Daters don’t need to be smooth-talkers. But the least they can do is be capable of holding exchanges.

The problem is that asking first date questions alone proves to be challenging for them.

Indeed, it sounds easy. However, only some are skilled in that department. If you aren’t among those people, here’s some relief: you can learn to manage.

Ease the tension on your first date; know which buttons to push. Here are some ways to prepare before heading into the line of fire and some suggestions on what to ask.

Pre-Date Preparations

Put your best foot forward with these timeless pointers:

#1: Prepare a list of questions or subjects

Are you the nervous type? Stay calm by compiling potential questions or topics in a list. You can write one down on a little notepad or store it in your phone’s notes app.

Having a list keeps the nerves at bay and prevents potential awkward moments. Look at our suggestions in the next section to get started.

#2: Don’t treat the date like a job interview

Dates should be fun! They shouldn’t feel like interrogations. Nobody likes being under a microscope, so don’t view them as applicants or candidates.

#3: Keep your expectations reasonable

First dates aren’t always as magical as fiction depicts them. Finding your lifelong partner is a great endgame, but this shouldn’t be a priority during initial encounters. This places unnecessary pressure on everyone, making for a less enjoyable experience.

Instead, keep your expectations grounded. Take your first date for what it is and enjoy the moment.

Great First Date Questions to Ask

Asking questions on first dates is one thing. However, asking compelling ones is another story. The former shows you’re uninterested, while the latter allows you to create a connection, so you could definitely go for this one.

We’ve gathered some questions that will get meaningful answers. For your convenience, we’ve divided them into specific categories to help you have an easier time picking out what to ask.

Scrambling to find great first date questions? Look no further than icebreakers.

Icebreakers

Is the tension so thick that a knife could cut through it? Create a relaxing atmosphere by throwing these first date questions out there:

#1: What are your pet peeves?

Get on your date’s good side by knowing what to avoid. Save yourself from bad impressions and dating faux pas by asking this question. Trust us; they’ll appreciate it.

#2: Are you a dog or cat person?

This wholesome question is a subtle way of gauging your date’s personality. They may have some similar traits to the animal of their choice. In turn, their answer can reveal bits and pieces about themselves that otherwise would’ve been left hidden.

#3: Where’s your favorite vacation destination?

This question can hit three birds with one stone. How? One, it gives you another hint of your date’s personality and lifestyle. Two, you get to hear their personal experiences and takes on travel. And three, it’ll give you clues about potential future getaways together.

The Basics

Now that the icebreakers have done their job, you can move on to questions relating to their background. Their answers will paint a general picture of who they are. Not only do they kill awkward silences, but they also make for great starting points for deeper conversations.

#1: What does your typical workday look like?

Is this a sign of something bigger? Hold your horses for a moment. This question doesn’t guarantee anything.

However, it does indicate your interest, which they may take as a sign to pursue something more with you. Place yourself in their shoes. You’d think someone cared enough to listen to how your routine plays out, which takes some time to describe.

#2: How do you kill your free time?

This may not be among the most thought-provoking things to ask on a first date. But hear us out: you have to start somewhere.

Who knows—it may kick off an interesting conversation. Your date’s answer may even be useful in the future as you try to help them relax.

#3: What’s your idea of a great weekend?

File this under the “small talk” questions folder, but it is, at least, a show of (slight) interest. This question is much better than dead air.

But before you get ahead of yourself, here’s a friendly reminder: this question isn’t an invitation. You’re still on your first date, so don’t jump the gun and insert them into your weekend plans just yet.

Interests

Now we’re getting somewhere! Learn more about your date’s personality (and vice versa) by getting to the specifics. Their answers may lead to meaningful conversations over overlapping preferences.

#1: What are your favorite shows at the moment?

Many people go to this question when they don’t know what to ask on a first date. Everybody watches TV! Whether through cable channels or streaming subscriptions, people have something to keep them glued to their screens. Their favorite shows could be the very ones you’re currently binging.

#2: What’s your favorite book?

We shouldn’t judge books by their covers. But we shouldn’t take them lightly either. A person’s reading selections can be telling. Whether fiction or nonfiction, it can give glimpses of somebody’s personality and values.

#3: What’s on your bucket list?

Not everyone has concrete plans, but most have things they want to tick off in life. Sharing bucket lists can be a great way to get to know someone because they’re snippets of people’s priorities. If your lists coincidentally overlap, they may be previews of potential shared experiences.

Serious Matters

At this point, you should feel comfortable enough to ask more meaningful things. Gauge your compatibility by asking these first date questions.

#1: What does happiness look like to you?

Happiness is universal, but it means different things to different people. Your outlook on the subject may be different from that of your date. Get a glimpse of their headspace by letting them explain their idea.

#2: What are you like when you’re alone?

Not even the most open books reveal the entirety of themselves to the general populace. They keep some cards close to their chests, which they’ll only draw when no one else is around.

This question encourages vulnerability—an important ingredient for a relationship’s survival. The answers will also give you much-needed views on themselves.

#3: What’s your idea of a healthy relationship?

Whether they’re experienced in relationships or not, your date’s answer is insightful. This sheds some light on how they approach love and determines how their perspectives align with yours.

No more feeling tongue-tied when you have our suggested first date questions in tow. Save this on your physical or digital notepad for future reference.

Feel free to expand this list of first date questions to ask her (or him, if you’re a woman reading this) by adding your own. There’s a lot of ground to cover, so satisfy your curiosity by including original ones.