Gina Florio
Updated October 28, 2016
Columbia Pictures Corporation

It can feel like there are a million things to worry about when you step onto the scene of a first date. You fret over whether you have food stuck in your teeth (maybe stay away from dishes with sesame seeds), who will pay for the bill at the end, and what the appropriate number of cocktails is to order throughout the evening. Most importantly, though, you worry about which questions to ask your hot date. There’s a fine line to tread here: You want to extract information in the most efficient way possible, but you don’t want to push the limit on your first outing together. (No wonder dates are so damn stressful.)

Not to worry, though. It’s normal to feel a little nervous about the list of questions, because it’s the very thing that will help you get to know the person you’re going out with — and it’s the very thing that might determine whether Round 2 is in the cards for you both. If you’re one of those people who draws a complete blank when they’re under any sort of pressure (which might happen if your dates turns up looking oh-so-cute), have a few of the following Q’s saved in the back of your mind for when you get stuck. Just don’t be surprised if your date has a few questions of their own waiting to make an appearance.

1. “What do you like to do with your free time?”


This is a really simple, drama-free way to find out what kind of hobbies your date is interested in. You want to know how they spend their evenings and weekends because if they love doing things you absolutely despise, it’s not likely that you’ll look forward to spending your days off together. Compatibility plays out in all sorts of ways, and one of the biggest factors that determines a good match is whether you two like to have a go at the same pastimes when you’ve got some time on your hands.

2. “What are your best friends like?”


The old cliché is true: You can learn a lot about someone by looking at who they spend most of their time with. Leaving a first date without finding out what kind of friends they have will probably leave you with an incomplete idea of who this person is you’ve been trying to flirt with all night long. Ask them things about what they like to do with their friends, how long they’ve been friends with their besties, and whether they get along with their friends’ partners. You may not even have to ask these things upfront, as they’ll probably come out in normal conversation, but it doesn’t hurt to have them tucked under your belt just in case.

3. “What’s your family like?”


This is a no-brainer. Learning about a person’s family life is a surefire way to gain useful insight into who they are as a person, and who they may be as a partner. Asking questions about their family can actually be a fun endeavor, though. It doesn’t have to be so serious. Figure out who their favorite sibling or uncle is. Guess which parents favored them when they were growing up. Joke and prod each other until you find yourself giggling and moving in closer for a little cuddle. You just killed two birds with one stone.

4. “Which Netflix shows are you into these days?”

Studies have shown that couples who watch the same TV shows may experience “greater inter-dependence, closeness and confidence” in their relationship. Having a mutual interest in the same programs can often bring partners together, even if they don’t share that many mutual friends IRL. So although it sounds like an offbeat question to toss out there, science urges you to uncover their Netflix preferences. It could be a solid predictor as to how your romance will turn out. Think of it this way: You couldn’t possibly see yourself with someone who hates blood and gore if Game of Thrones is your all-time favorite, right?

5. “Do you enjoy your job?””

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Without a doubt, you’ll ask each other what you do for a living. In fact, that will probably be one of the very first questions you put on the table. However, inquiring as to whether they like what they do is just as important. It will help you understand who they are on a deeper level, as well as gain insight into what factors they consider when making major life decisions. Besides, you want to be with someone who has a general joy for life, and that includes being fond of the career they’ve chosen for themselves.

6. “If you could go anywhere for your next vacation, where would it be?”

Taking a getaway together is one of the most fun things you’re going to do with your future SO, so make sure from the beginning that this person has the same idea of relaxation as you do. The last thing you want is to end up with someone who prefers mountain trekking over the ocean, when you’re a total beach bum. Asking innocently on a first date what their ideal holiday would be is a solid start to figuring out whether your tastes match up.

7. “Where do you see yourself living in five years?”

Just in case things pick up momentum between the two of you and you fall easily into a relationship, you’ll want to know that you can see eye-to-eye on big life decisions. One of these decisions is where you’re going to live. You don’t want to arrive at your one-year anniversary to find out that your SO is dying to move to the countryside, yet you can’t imagine life anywhere else but the city. It’s better to figure out all that sensitive information as soon as possible.

8. “How did your last relationship end?”


Yep, it’s a pretty serious question, but that’s okay. It’s something worth knowing, since it will probably tell you what they were lacking in their last relationship (in other words, what they’re looking for in their future one), how they’ve been hurt in the past, or what their expectation of commitment is from a partner. If they’re not ready to share this information yet, that’s fine. No need to push it. But most of the time, if things are going well, the person sitting across from you won’t refuse to answer such relevant questions.