The thing that cracked it open for me was Dale Carnegie "How to Make Friends and Influence People". It is very old fashioned but the core message is evergreen. People aren't interested in you. They are interested in themselves. The more you are interested in them the more interested they will be in you. They will eventually want to know what's on your mind but only because it's a mind that shares interest.

This sounds kind of manipulative because we are only doing it for attention. But the thing is people can smell that from a mile away. You actually have to BE interested and remember the things. You can't just pretend to listen or you will get the opposite effect.

One thing I've learned, is to be comfortable with some silence, and taking a moment to think. I'll even announce "hang on, I need to put my words together right" and then just internally monologue my thoughts into order while the other person waits for me to speak again.

Usually, there is no rush, we just imagine others to be impatient and feel pressure for no real reason. But really, there's no reason a conversation requires words be spoken non-stop. In fact I've found that when I force these breaks, the other people participating use the time to do some silent thinking, too, and come back with more thought out things to say when the conversation resumes.

Especially if you find yourself more comfortable with texting, where you can lay out your sentences and edit them until they feel right, you might just need to learn to do the same thing face to face.

A lot of conversation is about listening, not speaking. However, if you engage in active listening, you might find the speaker will look at you more, allowing you to add in your two cents.

Bit of a left field suggestion but one thing that really helps is finding your people.

In my younger years I sometimes really struggled with casual conversation, I often felt like I was the weird guy who had nothing to say.

It turned out that was only really true when I was spending a lot of time with people with whom I had very little in common. As I got older I eventually found "my people". Friends who I click with, who I share values and interests with, who communicate similarly to me.

It's not about finding people who are just copies of you, that would be pretty boring and make for a real social echo chamber. You want a range of friends with different interests, from different walks of life. But you want them to be, for lack of a better term "compatible" with you.

If you happen to be neurodivergent then that adds a whooooole extra layer of complexity to conversational compatibility. There's a stereotype that autistic people are awkward or socially inept, which is complete rubbish. They just communicate differently to neurotypicals. Put a bunch of similar autistic people in a room together and watch them have no trouble at all making conversation with each other, in their own style.

Anyway, maybe this isn't relevant to you, and you're already happy with the people in your life. But it's worth taking the time to examine whether the reason you struggle to make conversation is because you're trying to make it with the wrong people.

You have to encourage the other person to do most of the talking.

There is the statement followed by question form of conversation.

Person A "I just got back from Hawaii last week."

You "I always wanted to visit Hawaii and never got the chance. What did you do?"

Person A "I went to the Pearl Harbor Museum and Memorial."

You "I love museums. One of my favorite museums is..."

The goal is to ask questions with statements in order to find something that you both enjoy. The purpose of the statements to let the other person get to know you and ask questions about you. Once that happens, you can move to statements and rely less on questions.

Conversations are a two way street.

Know a little bit about a lot of things.

Conversation is about flow. Ask aquestion, get an answer, respond to that, they respond to you. If you know a little bit about a lot of things, and you always have some way to respond to what they've said.

But also learn to take the hint. If they're giving you one word answers, they may not want to be in the conversation.

A trick that I don't apply myself as often as I should: ask open ended questions, such as, "Do you think the rocks are quiet because they dont want the trees to listen?" Or maybe you can try a spicy one, "If you were president of the United states how would you solve the Israel-Palestine conflict" and then they'll be forced to think and give a long answer and leads to a discussion and possibly a bonus fistfight.

Try to refrain from asking questions with simple answers like "where are you from?" because then they'll answer "Washington", followed by an awkward silence while you try to figure out what to ask next.

Conversations are more about listening than talking. I suggest reading "How to Win Friends and Influence People" for a more in depth overview. Essentially, become genuinely interested in the person you are talking to.

Try to understand them. Try to figure out what is important to them and ask questions with these interests in mind. By being interested and asking questions that the other person wants to answer, they will do a majority of the talking and will feel like you are a great conversationalist.

Of course, sometimes this is easier said than done.. and it must be done genuinely. You must be genuinely interested. There are subconscious cues you communicate when you are interested in someone, and everybody loves being the focus of someone else's deep and genuine attention.

Once you've done this and built up rapport, then you can give personal anecdotes or get to your sales pitch or what have you.

Some other general tips are - speak slowly! Don't go overboard obviously but slower is more confident and puts people at ease. Say the other person's name when appropriate. Everybody loves the sound of their own name. Compliment people on things you genuinely appreciate. Nobody likes flattery but everyone likes being appreciated.

Tell me about yourself and let's see what we can do

Really? That's interesting what does that involve?

Basically get someone to talk about themselves

Have you tried Toastmasters? Yes there is a large part about public speaking but meetings also have dedicated improvisations. You could even work on areas of public speaking you didn't even know you might want to improve.

Try to respond to what the other person is saying, repeat their point back to them. That should give you a little time to think about what you want to add to the conversation, and will also keep the person engaged because they know you understood them. Example:

A: I don't know what to talk about...

B: Yeah, A. Sometimes I don't know what to talk about either. How was your weekend?

Example 2:

A: Did you hear about [current event X]? Seems like [person Y] is up to something big!

B: Yes, I heard about [X event] the other day. or No, I haven't heard about the [X event]. (Here you can add your initial impressions, thoughts, ideas or questions on this topic, or just "seems interesting" if you want them to tell more about it.

Example 3:

A: I think that [some opinion or thought about something, which you may or may not agree with].

B: I know what you mean when you say... [repeat a one sentence summary of their thought or opinion]. (Now you can go with your review of that thought or opinion and what your thoughts are on it.)

This can help let the conversation go smoothly. The important thing is that you let the person you speak with feel heard, then you'll be provided some space and time to add your own thoughts.

i also suck at this. i noticed if i interject with a question in a given conversation.. it provides an 'on ramp' for participation.

I use the Cinco Face Time Party Snoozer. I can be outgoing and social while catching up on some much needed ZzZz's.

Ultimately…. Practice.

Small talk (or more talk,) is a skill, some people have some natural aptitude, but it usually needs development.

You can start with small talk- especially with strangers or acquaintances. Quips about the weather, or if they ask that ever so annoying “how are you”- with no real desire for an actual answer (like 99% of the time,) something like “oh, one day better than Monday.” Usually gets people to pause, maybe smile. Maybe even a chuckle.

As you get more familiar, ramp it up. Ask about their favorite book, or maybe ask about something they mentioned last time. Maybe if you know what the do, ask something relevant to current events they might have insight on. (They might not shut up,)

The hard part is getting started, though, it’s best to practice in social spaces- maybe library events or social clubs surrounding activities.

Keep in mind, it’s okay to not fill the silence. It might feel awkward, but if there’s nothing to say, leave it at some ironic comment about the weather.

mostly, don’t be nearly so self conscious- all the stupid things we kick ourselves over… most people never really notice. Just sit back and ask questions, let them steer the conversation. It’s okay to ask stupid questions, as long as it’s actually sincere.

Lots of great advice in here! To add my 2 cents, I’d check out The Art of Captivating Conversation by Patrick King. That was recommended to me from some colleagues, and it’s not a super long read. Good luck OP!

When in doubt ask questions. Try to actively listen to what people are saying, think about what they're saying, and just ask any questions that pop up in your head. People love to talk about what they're passionate about, especially questions, it shows you're engaged. You don't have to have any original idea or contribute anything, just a series of questions. At the end of the conversation the other party will feel like oh I had a great conversation, even though you didn't contribute or volunteer any information. You especially see this in diplomats and negotiators, they don't need to tell you anything about themselves, they just need you to feel good about talking to them.

So just listen for a bit, when somebody mentioned something think about it, start asking questions. You don't have to provide any anecdote on your own to have a successful conversation.

The Ford method is a good one. I think?

Same as any other skill. Practice.

Most older folks still remember a time before cellphones, when strangers started chatting spontaneously. A simple commnet like 'That's a cute kid,' or something about the weather will start a conversation.