Somehow I didn’t figure these things out until around age 18. Keep reading to learn from my mistakes, or just laugh at my general awkwardness.
When you first meet someone, follow the script
I used to give a different sort of answer every time someone asked me a basic conversation-opener question.
For instance, if they said “Hey how was your weekend?” and I’d had an awesome weekend, I’d reply with a 5-minute play-by-play of exactly what I did and what was so great about it. Or if I hadn’t done anything that weekend, I’d reply “Good, I didn’t do that much though.”
After listening politely to my monologue, the other person would usually pick up on some thread in my story and ask me about that, and the conversation would move right along. Unfortunately, I would be so busy responding to their questions that I’d forget to ask them anything about themselves. How I came across: friendly, chatty, ramble-y, and self-centered.
If I’d given the “didn’t do much” answer, the person would often respond cheerfully “Lazy weekends are the best, huh?” And then I (wanting to make sure they got an accurate impression of me) would say “Well I actually don’t like staying in doing nothing, so I was kind of lonely and bored. But oh well.” At this point they would look confused, state “Okay then,” and change the subject. How I came across: weird, not interesting, deserving of pity.
So the flow of conversation depended on however I happened to think my weekend had gone—which was basically random.
I let my icebreaker conversations be dictated by fate for years, never knowing there was a better way, until one day my friend told me she just gives a one-sentence answer, then asks the same question back.
For example: “Good, thanks. It was my friend’s birthday on Saturday, and then on Sunday I had a long walk in the park with my dog. How about you?”
I was amazed by the simplicity of this formula. Suddenly it all made sense! And my life was much easier from then on.
If they’re distracted, wait for a better time
If you don’t have someone’s attention, there’s no point speaking to them. You can’t shout your way into getting someone to listen to you.*
Feel free to start speaking, but if you notice they seem busy, or flustered, or clearly have something else on their mind, just say “Never mind, I’ll come back later” and go about your business silently.
If they look at you as if realizing you’re there for the first time, and start apologizing profusely (while trying to juggle whatever else they were doing at the same time), say “No worries! It wasn’t important anyway! Good luck with whatever you’re doing :)”. Then stop talking and give them space.
If it was important, say “That’s okay, let’s find a better time later.” Go about your business silently. Later, text them to say “Hey, about our convo from before – when’s a good time to talk?”
What do you do if they’re never listening because they want to avoid having the conversation entirely? I don’t have a good answer for this one. My default response is to corner them and give them an ultimatum: either we have this conversation or I give up on you. I think continuous refusal to engage means you have to end the relationship (at which point they’ll probably claim to feel blindsided).
*Although if you’ve just found out there’s a bomb in the building, you can, of course, shout your way into being listened to by running around yelling “Everyone get out! There’s a bomb!” So an exception to the no-talking-faster-and-louder-when-people-aren’t-listening-to-you rule is if you have information that is imperative for other people to know, and they don’t know that you have it.
When you don’t know what to say, say what you want (to have happen)
When you feel stuck in a conversation, check in with yourself and ask “What do I want?” Then express that.
One time I had just gotten off the bus near my friend’s house and she and her boyfriend came outside to greet me. So after the initial hugs, we were standing there chatting when this random guy got off the bus and called out to me “Hey you with the green umbrella, you are so beautiful!” (It was raining.)
Then he strode right over to us, stood in our circle, and started trying to talk to us (with rapid-fire questions like “How are you guys, what are your names, where are you from…”).
My two friends just stood there looking surprised and confused. All I could think was “I would like this guy to leave us alone so I can keep talking to my friends.” So while he was mid-sentence, I said kindly, but firmly, “That’s very nice. Could you leave us alone now please?”
There was no need to make him feel bad about himself (he didn’t seem threatening, just odd and like he didn’t understand how to approach women) so I said it with a smile and without changing my stance or posture at all.
He seemed taken aback but not offended, and said “Okay, hope you have a nice day. I just wanted to talk because you are so pretty. But I’ll leave you alone now.” He said all this while backing away from us, and then he slowly loped off down the road until, with one last shout of “You’re so beautiful!,” he faded from view.
My friends looked relieved. They said they had felt frozen in place, had no idea what to do, and were glad I had the miraculous ability to get rid of weird people like that. But it’s not miraculous, really. It’s simple: You need never be at a loss for words if you just think “What do I want” and then say it!
What if the person seems threatening or unpredictable?
One time my friend (the same one from the previous story!) and I were at a McDonald’s late at night when I noticed this weird, seemingly drunk/high guy leering at me. We were sitting at a booth and she was across from me, with her back to him, so she didn’t notice.
After the guy made lingering eye contact with me three times, I said “Do you have a problem?” He mumbled something and shuffled off.
I kept an eye on him as he roved around the seating area… but then all of a sudden, he came over and sat down on my bench.
This time there would be no smiles or extending of the benefit of the doubt. I interrupted him mid-sentence, and said, loudly enough for the cashier to hear, “I don’t want to talk to you. You need to get off this bench and leave us alone.”
When he didn’t move—just kept sitting there and leering—I said “We’re leaving now,” stood up, and gathered my things (my friend knew to do the same without my needing to tell her, of course). Then we hustled out of there (checking to make sure he wasn’t following us) and quickly walked to my car, got in and locked the doors, and drove away to the other end of the parking lot (where we stayed, doors locked, to finish our fries—priorities, people!).
It was definitely a scary experience. I told my friend I wasn’t sure what I would have done if he’d followed us out the door… probably yelled “RUN!” and sprinted across the parking lot, hoping she’d be quick enough to follow. (Or able to call the police while he chased me.)
In retrospect, I should have shouted at the McDonald’s cashier as we were leaving, “This guy is bothering us. If he follows us out the door, call 911.”
(My dad, who’s a criminal defense lawyer and hence knows what he’s talking about when it comes to crazy people, says I should always just call 911 immediately. That is, I should have gotten up and dialed as soon as the guy sat next to me.)
My friend, on the other hand, generally thinks the odds of us being murdered are so low as to be negligible (so we shouldn’t allow fear to inconvenience us). I wasn’t sure how she would react to being forced to leave our favorite late-night hangout spot.
But she said “Woah, at first I was surprised you spoke so aggressively, but I see now it was really warranted. I thought for sure he would move after you told him to! What a crazy guy.”
Conclusion: When someone demonstrates that they don’t respect your boundaries, your top priority is to put enough distance between you (whether physically or emotionally) that they can’t harm you.
What if you just want to exit a conversation politely?
Since the previous section turned into more of a warning/public service announcement, here’s a proper conversation tip. This one comes from Ramit Sethi: when you’ve had enough of talking to someone, such as at a party or networking event, just shake their hand firmly and say “Well, it was a pleasure chatting. I’m going to go wander around some more.”
This is much better than making up an excuse like “I need to go to the bathroom,” because then you are free to engage someone else in conversation immediately, not forced to go to the bathroom when you don’t even need to (or insulting to the person, if they notice you not even bothering to go to the bathroom, and hence clearly having made up an excuse to stop talking to them).
Don’t sweat the details
You don’t have to answer every question to the best of your ability. People often don’t care about the accuracy of your answer; they just want to make conversation, or find out a little more about you (and then get back to their turn to speak).
So don’t bother to revise what you just said over and over because you fear it may not have been completely accurate (unless the person asks for clarification, or you’re testifying in court). You’ll come across as more sane and powerful if you just let what you said stand, even if it’s not exactly what you meant to say.
Likewise, you don’t always need to completely understand what someone else is saying. Sometimes interrupting their story to ask a question does more harm than good. To paraphrase Emperor Kuzco, don’t throw off their groove! Instead, just follow along as best you can and let them share how they feel about whatever they’re talking about.