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One tip -

You can't just ask questions without offering your own answers, or else it will seem like an interrogation. The more open you are, the more open they will be. Click ahead to get started.

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What are you thinking about these days? -

You may get a superficial response, but you can always frame that response in a larger context to press further.

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What is the first thing you noticed about me? -

This is a great question that most people are curious to know, but which also brings things to an intimate level without having to do the heavy lifting yourself!

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What is your love language? -

Your love language, how you personally prefer to give and receive love, is a lot of fun and really enlightening for two people to learn about each other. Take the test together if you haven't already, and compare your results.

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What do you like most about yourself? -

You’ll see what they value very quickly.

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Have you ever had an unrequited love/crush? -

It takes real humility to answer this question honestly.

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Do you think there is a difference between having sex and making love? -

Sex is a big part of life—after all, it’s how most of us got here—but people have very different views on the meaning of it.

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What frustrates you most right now? -

This is one of the easier questions to answer since most people are waiting to vent about their frustrations, but it’s also indicative of where this person's head is at.

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What do you want people to remember about you? -

A legacy is something some people perhaps haven’t even thought about, while others feel very motivated or pressured by it.

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Have you been in love before? -

We tend to assume everyone has the same idea about what love is, but it is so enlightening to hear other perspectives. A follow-up is: have you ever had your heart broken?

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What do you miss most from your childhood? -

This is a great segue into swapping childhood stories.

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How would you describe me to other people? -

Not only is this a nice little confidence boost for each other, but you share what you both find distinctive about one another in a less nerve-wracking format.

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Would you say you have a "type"? -

This is especially interesting as sometimes people are embarrassed about their “type,” evident in their past relationships. You can talk about what it means to have a type and whether you fit each other’s.

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What is something you think is true about me but haven’t asked? -

This is a great question because it requires another question and answer.

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What is the best compliment you ever received? -

This is a warm and fuzzy question that will not only make your date happy to think back on, but will also reveal what they love and value most in themselves, and how they want to be seen. 

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Is there something you always wanted to try in bed? -

Some people have never had the courage to ask for different things in bed, but most people are a little curious!

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Who is your role model in life? Who is your role model in love? -

It’s always interesting to see if the answers to these two questions are the same or different people, and why.

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What do you think the role of marriage is in a relationship? -

This question yields very different answers!

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Are you aspiring to anything? -

Sometimes we harbor secret dreams that we never get asked about because people tend to focus on pragmatic next steps.

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Do you have a proudest moment? How about a least-proud one? -

Dive all the way in with each other's biggest achievements and most shameful acts.

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Do you have any regrets from your past? -

A juicy follow-up question can be asking if they’d like to do something about that regret now.

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How important is physical attraction to you? -

For some people, a relationship isn't a possibility without it, but for others it comes second to other traits like humor, confidence, or kindness.

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Is there something you’re scared of that you feel comfortable telling me about? -

You can preface by talking about collective fears or your own fears so that it’s a less abrasive segue.

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What are you most confident in? Least? -

The wording leaves the possibility for someone to answer about their confidence in themselves or in subjects, products, institutions, etc.

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Do you believe in an afterlife? -

You’re probably the best judge of whether you want to bring up religion, but death is something we all have in common, so it’s a fantastic topic!

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Could you die happily without ever having had children? -

Even if they have children, find out whether they felt that they needed that experience before having them.

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Do you believe in love at first sight? -

Some people believe in an immediate transfer of energy, others think it’s completely superficial. You can decide for yourself!

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Can you remember a moment of falling in love? -

Ask them what it looked like, how it felt, how they knew, etc.

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What’s one thing you don’t like about yourself? -

In an intimate conversation, you won’t get the same interview-type response about their biggest weakness being that they’re "too much of a perfectionist."

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Do you have a fantasy? -

This question deliberately leaves it open to whether it’s sexual in nature or more idealistic in terms of a dream job/life/world.

Now you’re ready: check out these date ideas you can pull off while in lockdown.

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