What are some good deep convo starters to ask?

What I recommend to help you have incredible and deep conversations is not to just skip from subject to subject. Very often conversations turn into interviews, where people will ask "How many siblings do you have?" "Where did you grow up?" 'What do you like to do for fun?" "Where did you go to college?" They go from topic to topic. But really great conversation happens when you take one topic, and then you go deeper with it. For instance, you might say, "Where did you grow up?" And the other person may say, "I grew up in Detroit." And you might say, "Wow, tell me about Detroit. What was it like growing up in Detroit?" or "I heard that Detroit is really having a renaissance right now. I heard that the city is really coming back to life," and you can start to really explore that. If you really stick with a single subject, exploring before just going around from topic to topic, it allows for much deeper conversation.

If we’re talking about dating, deep conversations probably shouldn't happen until the fourth or fifth date because we want to try and keep it light. And deep conversation starters usually should happen organically . Say you already know the dynamics of his relationship with his parents, or maybe he was married before, or he’s divorced, or maybe he's got a big change happening in his life. You might start with, “Okay, you mentioned …” and bring it back to the original subject. For example, saying, “You mentioned that your parents got divorced just recently. How does that make you feel? Has that changed your values on marriage?”

Come to the conversation from the point of view where you are just an observer, and you're just asking a question because you're curious about his welfare or her welfare. That way, you're going to give them a safe space to be able to talk. You don’t want to appear to have an alternative motive to try and learn everything that you can possibly know about them to then drill them and turn it into an interview. And then the key is, once you ask one of these deeper questions, sit back and listen because people will speak more when there is silence.

If you're dating someone and you feel like it's trying to get blood out of a stone to get the conversation going, especially about important topics, because if you really want to have a relationship with this person you need to know more about them than just surface level, then say less because what you will say will be more poignant and they'll be paying more attention to what it is that you're asking. Then, listen and affirm what they're saying , maybe try saying, “Okay, I understand”.That should lead to the next question, and the next question, and it should flow a little bit more because they will be revealing more. Then you will have the next step to the next layer of that conversation because you're giving them a safe space to be able to talk in depth.