Most of the advice on making conversation I’ve come across focuses on what to say and how to say it. You know: make eye contact, ask open-ended questions, be a good listener, be up-to-date on current news and events, avoid loaded topics, etc.
I’m going to pull back and look at some of the ‘bigger picture’ factors that can affect how easy it is to talk to others. I’ll give some ‘bigger picture’ advice on making conversation as well.
There are factors that help or hinder a conversation before it starts
When it comes to social interactions, I’m a big believer in the idea of ‘the outcome of a battle is decided before it even starts’. When you chat to a bro from work or a cute girl at a party, many of the factors that determine how well the conversation will go are already in place. Some of them are:
Your basic personality, skills, interests, knowledge, outlook on life, etc.
How you come across to people and the overall impression you make.
This will determine things like whether people want to talk to you, for how long, the attitude they bring to the table, topics they’ll bring up or avoid, etc.
How eager the other person is to talk to you. Related to the point above. They decide this on their impression of you, their previous experience with you, their previous experience with similar people, any preconceived notions they have about you, etc. Also included here are things beyond your control like what kind of mood they’re in, etc.
Whether you have anything in common or to talk about with the person.
Whether you’re off-putting or intimidating to the other person in some way. Things like being very good-looking, having a higher career or social status, or having a certain reputation can intimidate people. Things like having a bad attitude, a weird personality, being awkward or creepy, being much less cool than the person you’re talking to, and bad dressing and grooming habits will put people off you. When people are intimidated or put-off by someone they’re more tongue-tied.
Conversation flows out of who you are as a person
You’re your own conversation generator. Someone who is cheerful, sociable, knowledgeable, witty, and interested in a lot of things will naturally have better conversations than someone who is depressed, negative, and kind of boring.
If you think of conversations you’ve had, you never really had to think of what to say, it all just popped into your head.
How you say something is as important as what you say
Someone who’s naturally funny/insightful/a good story teller/etc. can take the same basic material as someone else and, as if they’re running it through a filter, make it more interesting.
Conversations don’t have to have any goals or proper progression
Reading some other advice on making conversation, you can get the impression that it has a certain structure and goal. Like first you must make small talk. Then you must move deeper. The goal is to get the know the person and connect with them.
That’s definitely true at times, but often they’re just fun for their own sake. Shooting the shit and joking around or talking about something interesting is also preferable to being bored at work or standing around and not talking.
I have friends I’ve never really ‘connected’ with. We just hang out and joke around and talk shit about random superficial topics that interest us. It’s great.
Having something in common you both want to talk about is a big key to conversing easily
The key phrase is ‘that you both want to talk about’.
There are certain things most people are interested in. Things like sports, movies, t.v. shows, music, and pop culture/gossip.
If you can figure out the particular sport/current movie/good t.v. show/new band/stupid thing some celebrity did that someone is interested in you can take off and start gabbing about it effortlessly.
It’s a big benefit to be up-to-date and interested in these things.
Some other popular topics when people start getting older are kids, work, and money.
Another key is being comfortable with the other person
You’ll have trouble thinking of things to say if you’re not comfortable talking to someone or that type of person. When you’re familiar with someone the words flow much more easily.
If certain types of people make you uncomfortable then aim to understand and get used to them. You can do this by hanging around them or by digesting the types of experiences that they’ve had (e.g., if you want to understand macho competitive people then play some sports and read material on sports strategy and coaching).
Read, read, read, learn, learn, learn
The more random stuff you have floating around in your head, the easier it is to chat with people. If you have enough stuff stored away in there then pretty much anything someone says will remind you of something interesting you can contribute.
A couple of times I’ve been reading about some obscure topic earlier in the day out of my own interest only to have it come up in a conversation that very night.
That ‘je ne sais que’ lack of rapport with people
We’ve all been in conversations where there’s just an awkwardness in the air that you can’t quite put your finger on. Talking to the other person is like pulling teeth.
Often this lack of rapport is because the two people are put off by each other in some subtle way. They perceive each other to have values or traits that they don’t like.
This can also happen when too people don’t like each other but are forced by their circumstances to be around each other.
It also happens when two people seem superficially similar, but on a more subtle level are actually from different worlds.
It’s a bit hard to explain, but one place where you can see this is in office environments between the people who make the products (R&D, Programming, Tech Writing) and the people who sell them (Sales, Marketing).
If there are certain types of people you have trouble talking to try to get in their shoes and see where they’re coming from. No one is really that bad once you get to know them.
Take the attitude that you will have to pull most of the weight in the conversation
If you’re half-decent at talking to people this is often true. Many people are awkward at making conversation to one degree or another.
It also puts the onus on you to develop your conversational skills and become more interesting.
Don’t worry too much about the technical details
If the bigger picture factors are solid, then you can get away with a lot when it comes to the little technical details. For example I have a bad habit of not making eye contact that’s a hold over from my years of being shy and inhibited. It would be better if I did make eye contact, but I can get by well enough without it.
Making artful segues are another thing you can often ignore. Just going …”Oh yeah” or “…oh, I just remembered” is fine as long as they don’t come totally out of left field.
Even lulls and long silences are no biggie.
Sometimes people just come to the end of a tangent and they both have to take a second to figure out what to say next.
Both people may just want to be quiet and relax for a second.
A particularly interesting or profound point may require both people to pause and digest it for a moment before it sinks in.
Obvious lesson one more time:
Take a look at yourself and see if there are any bigger picture factors you can improve to make future conversations go better.
People who have trouble with conversations often have trouble in these areas. Ask yourself:
Is there anything about your personality or attitude that could use a tune-up?
Could you improve the impression you give off to other people, perhaps by changing your look?
Are your interests a bit out of sync with what most people are into?
Are you so socially inexperienced that you’re uncomfortable and unfamiliar with most types of people?
Are you so socially inexperienced that you’re too lacking in commonalities with most people?
Hope this helps!
A final random thought: In books and articles about making conversation, why are the example phrases they give you always so long?
You know, they’ll say things like: “It’s important to ask open-ended questions. A good tip is to ask about a current topic in the news such as:
“I was reading the paper the other day and I saw an interesting story. It explained that the fallout from the United States government’s nuclear bomb testing in Nevada in the 1950’s is still in the soil and may be causing Hispanic women in their 30’s and 40’s to be more likely to develop ovarian cysts. What do you think about nuclear fallout and it’s consequential environmental impact on subsequent generations?”
Why not keep it brief and say something like: “Did you read that fallout story? What do you think???”