More than 2,000 years ago, Theophrastus described a man who sat beside a stranger and talked endlessly about his wife, his supper and the weather. His warning was simple: "unless you refuse to listen, he never stops" (Characters, "The Garrulous Man", Charles E. Bennett and William A. Hammond's translation).
The weather was never the problem. The problem was that Theophrastus's talker never gave the stranger a turn.
Cicero later noted that there were rules for public speaking but none for conversation, and he suggested a few of his own (On Duties 1.132, Walter Miller's translation). Plutarch, in turn, wrote about which questions people most enjoy being asked.
Modern research suggests the effort is worth it. In one set of experiments, commuters who were asked to talk with a stranger reported a more positive journey than those who kept to themselves, even though people predicted the opposite. One reason was that they underestimated how interested others were in connecting (Journal of Experimental Psychology: General, 2014). Here are ten simple phrases that can help a first conversation go well, drawing on that old advice.
1. "Mind if I join you?"
Starting is often the hardest part. The commuter study suggests that many people overestimate the risk. Other people were more interested in connecting than participants expected, and the conversations were more pleasant than predicted.
A simple, polite opener gives the other person an easy way to say yes, and an easy way to say no if they'd rather be alone. "Mind if I join you?" or "Is this seat taken?" works at a conference table, a party or a waiting room.
If they seem busy or reluctant, a friendly "No problem" lets you both move on without awkwardness. Often, though, the answer is yes.
2. "How do you know the host?"
Cicero observed that conversation usually drifts toward a handful of subjects, such as home, public affairs, work and learning. He also advised paying attention to the people present, "for we are not all interested in the same things at all times or in the same degree" (On Duties 1.135).
The easiest place to begin is whatever you already share. At a wedding, it's the couple. At a conference, it's the event. At a neighbor's barbecue, it's the neighbor.
"How do you know the host?" or "What brings you here today?" gives the other person something concrete to talk about and often leads to a story. It's also much easier to answer than a vague "So, tell me about yourself."
3. "What's been keeping you busy lately?"
Plutarch, writing about conversation at dinner parties, noticed something about the topics people raise on their own. "Whatever we are wont to discourse of though unrequested," he wrote, "we are desirous to be asked" (Table-Talk 2.1, from the translation revised by William W. Goodwin).
In other words, people often have something they'd like to talk about. A good question gives them permission.
"What do you do?" can work, but it steers the conversation toward jobs, which not everyone wants to discuss. "What's been keeping you busy lately?" leaves room for anything: a new puppy, a renovation, a work project or a trip. Whatever they choose is usually what's on their mind.
4. "What do you enjoy most about it?"
Plutarch offered some practical examples: "You please a hunter if you ask him about dogs, a wrestler about exercise." Many people light up when the conversation turns to something they care about (Table-Talk 2.1).
Once someone mentions a hobby, a job or a project, a follow-up about what they enjoy invites them to talk about the good part. It's often more interesting than the facts, too. Two people might both coach their kid's soccer team for very different reasons.
"What do you enjoy most about it?" or "What keeps you coming back to it?" tends to work far better than a question about logistics.
Questions work best alongside a little of your own experience. An exchange might go like this:
Them: "I've started growing vegetables."
You: "I tried tomatoes last year and mostly fed the insects. What are you growing?"
A small detail about yourself gives them something to respond to as well. You can be curious and let yourself be known.
5. "Have you been anywhere interesting lately?"
Plutarch noticed that "travellers and merchants are most satisfied when their company is inquisitive about other countries," and are happy to describe the places they've been (Table-Talk 2.1).
Keep "somewhere interesting" broad: a nearby café, a park, an exhibition or a visit to another town all count. "Found anywhere good around here lately?" is an easy local version.
6. "How did you pull that off?"
Plutarch also observed that "more genteel and modest men love to be asked about those things which they have bravely and successfully performed, and which modesty will not permit to be spoken by themselves before company" (Table-Talk 2.1).
Many people have done something impressive that they'd never raise themselves: running a marathon, renovating a house, moving across the world. When they mention it in passing, a question gives them a chance to tell the story without sounding like they're bragging.
Plutarch added a caution worth keeping. He advised "never to ask a man about his own calamities." Early in a conversation, it's usually kinder to follow someone's lead on difficult topics than to dig into them.
7. "What was it like back then?"
Plutarch had a particular piece of advice about older people. "He that enquires any thing of an old man, though the story doth not at all concern him, wins his heart," he wrote (Table-Talk 2.1).
Older people often have experiences that others rarely ask about: what their town was like decades ago, how they got their first job or how they met their partner. A question like "What was it like back then?" shows genuine interest in a life that may feel overlooked.
The same principle works with anyone who has more experience than you in something. "What's changed since you started?" can open a long and interesting conversation.
8. "What's something you're looking forward to?"
Small talk doesn't have to stay small. In a series of experiments, strangers who had deeper conversations found them less awkward than they expected and felt more connected to their partners than after shallow ones. People tended to underestimate how much a new acquaintance would care about what they shared (Journal of Personality and Social Psychology, 2022).
That doesn't mean jumping straight to heavy topics. But once the conversation has warmed up, a slightly bigger question can be welcome. "What's something you're looking forward to?" invites people to talk about what matters to them without putting them on the spot.
Let their answer set the depth. They might mention a vacation, seeing a friend or finishing a difficult week. Follow whichever part they seem happy to discuss.
9. "What's your take?"
Cicero thought good conversation should be "easy and not in the least dogmatic," with "the spice of wit." He also warned against treating it like "a private monopoly." Instead, a good conversationalist "should think it not unfair for each to have his turn" (On Duties 1.134).
Sharing your own view is part of conversation. But stating it as the final word tends to close things down, while inviting the other person in keeps it moving.
After you've offered an opinion, "What's your take?" or "Do you see it the same way?" hands them a turn. It also signals that you're interested in what they think, not just in being agreed with.
10. "I'll let you mingle, but I'm really glad we got to talk."
Cicero also had advice about endings. "As it had a reason for its beginning," he wrote, "so there should be a point at which to close it tactfully" (On Duties 1.135).
Many people stay in a conversation too long because they don't know how to leave. A warm exit is easier than it seems. "I'll let you mingle, but I'm really glad we got to talk" ends on a positive note and frees both of you.
If there's a natural follow-up, mention it: "I hope the move goes smoothly" or "Let me know how the race goes." It shows you were listening, and it leaves the door open for next time.
Phrases help, but attention does the real work
No phrase works if it's delivered on autopilot. The point of each one is to give the other person room to talk and to show that you're interested in the answer. If you ask a good question and then check your phone, the effect disappears.
It's also worth remembering that small talk is harder for some people than others. Shyness, social anxiety, cultural differences and neurodivergence can all affect how comfortable a first conversation feels. And some people simply don't want to chat, which is fine. A friendly opener that gets a short reply isn't a failure.
One place to start
Pick one phrase from this list to try at your next gathering, meeting or even in a line at the store. "What's been keeping you busy lately?" is a good first choice because almost anyone can answer it.
Then do the part Theophrastus's talker never managed: listen to the answer, and let it lead to your next question.