Learning about it can really teach you whether your friend has plenty of determination or if they choose to wisely retreat and fight another day. Why It's Great: It's important to know whether a person would give up, but also why. Is there ever a time when giving up makes sense? So, be a little careful when asking this, and make sure to be more welcoming than amused when you ask it. It made the other person think I was calling them old - that's because I asked it while laughing. Who NOT To Ask It To: I completely flopped this one when I asked it for the first time. They can feel younger than they actually are or even older - the answers are all different. Who To Ask It To: Just about anyone can be asked, but it's ideal to ask someone who is old enough. Are they older than their years or still a child at heart? The answer can be profoundly deep and great for talk. Why It's Great: Talking about age and life is something so universal everyone knows how to answer it, which makes it something anyone can ask. Who NOT To Ask It To: Some people don't like being asked about their closest friends, so wisely change the subject if you encounter that. That way, you can ask them afterward, and compare their answers. Who To Ask It To: The best people to ask this question would be someone whose family and friends you know. Are they honest, responsible, or messy? Are they simply just sharing their opinion about themselves, or do they really believe it's how their friends and family see them? This can spawn plenty of meaningful conversations, so be prepared to spend a while. Why It's Great: It may seem like a personal thing to ask, but it's a great way to get to know someone because it can reveal how they see themselves. How would the people closest to you describe you? Who NOT To Ask It To: Asking someone who has gone through tremendous tragedy, grief, or a highly private and delicate issue would definitely be inappropriate, so avoid asking this. They could provide their perspective on why they didn't do it. Who To Ask It To: You could ask close family members or friends about this - basically, people you know well. When did they miss out on being the hero? Why did they fail, and how would they change it now? Swapping stories and digging for more details by asking the right questions really helps you have a deeper connection. Why It's Great: This is sure to be a deep and interesting conversation. If you could go back and do one good deed that you had the opportunity to do but didn’t, what would it be and why? Who NOT To Ask It To: Pessimists might not be the best people to ask this to, unless you're interested in what they have to say. Who To Ask It To: This is always a good conversation starter among newly-found friends or partners! Talk it out with wine or over a meal, and you've got a recipe for a fun time! Everyone has their own opinion, so you'll have a lot of different answers. Why It's Great: You'll get a great debate going between the optimists and the pessimists about everyday life and whether a positive outlook has an impact. Can a positive outlook make any situation better? Who NOT To Ask It To: It'd be awkward nonsense if you ask your ex this one, wouldn't it? I bet you definitely wouldn't want to hear them say they'd spend it with you. A solid friendship is built on whether we can choose to spend our last day with someone we love. Who To Ask It To: This one's perfect for asking close friends or even your partner. Are there fun things you've always wished to do? You can follow this up in so many ways. It has you really thinking about what's most important in life. Why It's Great: Our mortality is always a deep conversation topic. If you found out you were going to die tomorrow, what would you do today? Spare them this question until you're sure they can handle it. Who NOT To Ask It To: The topic of life challenges is a sensitive topic for those dealing with their mental health. As they share their answers, you'll also have time to catch up with them and give your own. Who To Ask It To: Reunite with your high school best friends and open with this question. Naturally, you'll also learn how they've overcome it. Why It's Great: You've given them a reason to give a deep thought about their past, and that helps them open up to you. What’s the hardest thing you’ve ever been through? Give it some time past the introduction stage. Who NOT To Ask It To: Asking a deep question like this to strangers you’ve just met, at a networking event, for example, can startle them. The latter is still in the formative stage, where they're deciding what to choose. Who To Ask It To: You can ask anyone, but it's better to ask adults rather than teens or younger. Why It's Great: This way, you can phrase asking whether they're an extrovert or introvert in a much less ordinary way. What do you think is more important: exploring the world or yourself?
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