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How To Have More Deep, Substantial Conversations

"No one I know ever wants to have more interesting, meaningful conversations. They just want to talk about fluffy, superficial topics, which gets dull after a while. Whenever I try to take things in a deeper direction no one bites." That's a fairly common complaint, especially from people who have more cerebral personalities and a 'quality over quantity' approach to socializing.

It's hard to precisely define what makes a conversation "deep" or "substantial", but you know one when you're having it. They just feel more mentally stimulating and fulfilling. Some typical "deep" areas are:

If you like talking about deeper topics it's not that you need all your conversations to be intense or intellectual, but you'll get discouraged if it seems like there's no option to interact on that level at all. It can make you doubt your relationship with someone when you feel like you can only engage with them on a more surface level, and have to repress a whole other side of yourself.

There's no way to have deep conversations on command

I'll share some ideas on how you can get into more deep conversations overall, but there's no method that I know of to get any particular people at any particular time to want to have a more in-depth discussion. That really goes for most kinds of conversation. If someone really likes sailing there's no sure-fire way they can get into a conversation about it whenever they want.

There are a lot of reasons someone may not want to have a deeper conversation. They may not be in the mood. They may not think it's the right time and place. They may not care about that particular topic. They may not have the background knowledge to talk about it properly. They may be capable of conversing deeply, but only do it with their partner or closest friends. And although it sounds a bit snobby, I don't think it's unreasonable to say some people just aren't as deep or intellectual as others.

By far the easiest way to have more deep conversations is to find other people who like having them

When you're with someone who's also curious and thoughtful and likes to talk about deeper topics it's almost hard for the conversation not to go in that direction. You don't have to force anything. If you tell several people you work as, say, a paramedic, some might reply with a, "Oh, I hate hospitals. I don't think I could do that." With others the first thing that comes to their mind is to mention an article they recently read about medical ethics.

This may not be the answer you were hoping for when you started on this article, but in my experience finding other 'deep' people is the simplest way to satisfy your urge to have more stimulating, cerebral conversations. For the most part there's no big trick to seeking them out. You've just got to meet more people and then try to get a sense of which ones veer towards having more in-depth interactions. I'd say there's some relationship between education level and 'deepness', though it's anything but a perfect link. You can come across PhD's who are oddly vapid, and factory workers who have thought more deeply about philosophical questions than you ever have. You may be able to find events and meet ups which center around stimulating conversation. For example, a Meetup.com group may focus on debating various social issues over coffee.

If your current friends and colleagues don't seem interested in having in-depth conversations I find it's always going to be an uphill battle to try to get them to go that way. Sometimes you can get them talking about something more substantial, but it's usually not as satisfying as you'd like it to be. They don't go deep enough, and it often feels like the conversation is going to revert to its default level at any second. Or you may be able to go deeper on particular topics, but not all the ones you'd like (e.g., you can get a friend to talk at length about their past relationships, but not anything philosophical or intellectual). It's just simpler to look for people who are more your style.

Just try bringing up the deeper things you want to talk about

People who want to have more in-depth interactions usually complain that they try bringing up deeper topics, but no one is keen, or even looks at them funny. The thing is you've still got to try. That's just what everyone does in conversations. They attempt to take them in directions they think would be interesting. Sometimes they get a response, sometimes they don't and they move on to something else. If one group of friends consistently doesn't care when you try to bring up deeper topics it's a sign you may want to try with another group. It's the same as if you really wanted to talk about basketball and none of your co-workers seemed into it.

Like I said, there's no way to have deeper discussions on command, but some situations are more conducive to them than others. If you're pre-drinking at someone's apartment and everyone's making dumb jokes and can't focus on a thought for more than thirty seconds, you're probably out of luck. If you and some friends are driving somewhere or having coffee, they may be receptive if you bring up that book you just finished, make an observation about the nature of power in society, or ask them what they really want out of life.

There's a guideline that if you've just met someone you should ease into trying to have a deeper interaction. I do think it can be jarring to hit someone with a really thought-provoking question or observation within a minute of meeting them, especially if it's about a more personal topic. However, I don't believe you necessarily have to make half an hour of non-threatening small talk first either. A lot of us can remember a time where we just met someone, were chatting about the usual topics, and then they took things in a deeper direction and we were happy to go with it.

I think it comes down to the other person's personality, what types of subjects they like discussing, and whether they feel like talking about them with you. If you quickly get into a deep conversation with someone it's not that you skillfully molded the interaction so much as found someone who was already on the same page. Again, it won't always work out but at least you can try. If it truly is your personality to want to talk about deeper subjects there's no shame in letting that show. It's as valid a thing to want to talk about as anything else.

Being comfortable with self-disclosure lets you have more deep conversations about personal topics

Even if you have problems opening up to others it's usually not about every subject. It's still possible to have a deep conversation about a personal topic you're comfortable with (e.g., you may be fine talking about your parents, but not your love life or insecurities). However, if you can get used to sharing more aspects of yourself with people it will open up further possibilities.

Be careful not to develop a dynamic with someone where you always talk about negative problem subjects

Some people discover that they can reliably have more meaty-than-usual conversations with a friend if they get them talking about their problems. The first few times this happens it can feel great - "Normally we talk about day-to-day stuff, but now we're opening up to each other and delving into our failed relationships." It's not a viable long-term strategy. It creates too many unpleasant vibes when the conversation is always being pushed in that direction. It may also unconsciously train you or them to be too quick to bring up negative topics.

If you're currently discouraged about not being able to get your deep conversation 'fix', realize it won't take much to feel better

I find if someone's really deprived of stimulating conversation they can feel they want to have nothing but deep, intellectual discussions, and that they hate more superficial topics. In my experience that's just the frustration talking. In my experience even the deepest people are fine talking about more shallow fare, just as long as they can get their bare-minimum 'deepness' needs met. You may not need to ditch your entire 'shallow' social circle, just find one or two extra friends who you can meet your need to talk about more profound or brainy subjects.