Here are 5 Questions You Should Ask on Your First Date

The first date is where and when the future of your potential relationship is decided. Before your meeting, all you have are mostly hopes that this person you’ve been communicating with turns out to be this way and not that way. You finally get to meet them, you get to see your hopes reaffirmed or shattered, and you get to see your fears verified or disproved. With a face to face meet, it becomes much clearer who the person you are dealing with really is (or at least you get a stronger sense of who they might be).
Conversation is the lens with which you’ll be able to peer into your date’s personality, their past, present, and a glimpse into where they might be headed. That’s enough information to decide whether to have more dates or not. But what do you talk about? What questions do you ask that sort of lift the veil on your date and lets you see more into who they might be?
Here are 5 questions you should ask on your first date. Of course, there will be a lot of questions, but these are like the punctuators of your conversation.

1. What was it like growing up?

Asking someone what their childhood was like is a great question for revealing someone’s foundation and the impact of that past on their today. Of course, you have to make it light and shouldn’t be like a therapy session. The biggest influence on someone’s life, needless to say, comes from the parents. Knowing how someone’s relationship was with their parents will give you an idea into what unresolved issues might spill into your relationship down the line.

2. Where do you see yourself a few years from now?

No one want’s to be with someone with no compass, who’s simply drifting on autopilot. It’s always a good idea to have a goal or two, even if these may never be achieved. Asking your date where they see themselves a few years on will tell you if you might have a future together.

3. What do you do in your free time?

What someone does in their free time may represents their innermost selves. They are not doing it for the love of money, neither are they doing it out of obligation – they just love it. It is a great way to know what kind of personality they might have. You can tell whether they are outgoing or more on the closed-up side by looking at how they spend their free time. Reading books? Watching movies? Parties with friends?
The question will also give you ideas about what to talk about. There is always that risk of having awkward silences spread around your conversation. But if you know their interests, you can find some common ground and talk about something you mutually have an experience with.

4. Who is you closest friend and what is it about them that makes them connect with you?

This may seem intrusive from a distance, but it’s not like you are trying to have a list of your date’s friends and their details. It’s just a light question about who their best friend is and what makes them connect. You will be able to know more about your date’s character if they can tell you about why they hang out with this person. As they say, iron sharpens iron; birds of a feather flock together.

5. What is your greatest fear/passion?

Passions and strong fears drive our lives and cause us to act in certain ways. Knowing what these are for your partner will allow you to understand them more. This might also be a good time to understand what your date’s core values are. You may not be able to ask what their core values are directly, but you can pick them up through questions like this one.


As earlier stated, the conversation should flow naturally and not like a therapy session at the psychologist’s office. You can have a lot of other fun questions like what your date’s nickname is and how they got it. This can make your conversation fun as most nicknames have interesting backgrounds.