I watched this video by the Youtube channel Improvement Pill, it was a pretty interesting topic of asking specific questions to open up more conversation to get to know somone better. I've jot down some notes here as a quick snippit so I won't forget them.

NOTE: this is just my own interpretation of it. Might not be exactly as it was in the video.

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Question 1

When someone tells you something about an experience they've seen or gone through, asking them how they felt about it bring out more of the emotions and thoughts they felt when it happend. This is great to understand the person, as different people might feel differently about the same thing happening. There might be some good reason behind why they felt that was as well.

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Question 2

When you're talking to someone and they're on a specific topic, it's interesting to hear if there is any personal take on the topic itself. Asking them "if they have ever..." puts them on the subject and let's them tell a more personalized take on that subject. Example, if someone is talking about scuba diving, asking if they have ever wanted to explore sunken ships in the Carribean might open them up to talking about how it's been a lifelong goal or that they only wouldn't dare try it.

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Question 3

The third one isn't a quote or a particular phrase, so no quote box here. The third thing to get to know someone better is to make an assumption based on the topic. It shows a few things. First, you are listening and showing some interest in their topic by being curious about it. Secondly, you allow them to go deeper into a topic that they have interest in or that gets them thinking about something they have never thought about before. Back to the scuba diving example, you might ask, "Is it true that scuba diving is the most dangerous tourist activity?" They might say, how it's not true but a lot of people think that because... etc. or they might say yeah, there's a lot of safety training involved because it's easy to make a mistake ... etc.

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Question 4

The last question to ask someone is to dig deeper into a shorter statment or experience they might have had. If they're talking about how they had the most amazing street food while traveling in South America, you could always dig a bit deeper by asking them to tell you about that trip or how that specific experience happened "What's the story about why you were in South America trying out street food?". You could even use it to get to know the story behind the story "Why did you go there?", "Who was there with you", "How did you know what to try?"

References

Youtube video by Improvement Pill: link 4 POWERFUL Questions To Ask In A One On One Conversation