12 Conversation Starters That Don't Sound Forced

Sira Mas

Years ago, I went for a coffee with my friend Elsa, and she invited a friend, Laura. The moment Elsa went to the ladies room, Laura and I had a conversation, which ended up being full of awkward silences.

This probably happened because we were both shy.

If you’re anything like me, you might have experienced awkward situations in which you were in front of someone, probably a new acquaintance, and both of you had no clue what to say.

What follows are some great conversation starters I put together for myself to prevent uncomfortable situations. These all help me avoid awkward silences, like the ones I experienced years ago with Laura, and to have pleasant interactions.

1. Is this your first time here?

I remember when I met someone who is now one of my best friends, Marta. She’s the girlfriend of John, a good friend of mine.

The day we met we were at John’s place. Later, we went to a Japanese restaurant downtown to have dinner. John left us alone for a few minutes as he had to take an important call. Before I could even think of something I could ask Marta to initiate a conversation, she asked me, “So, Sira, is this your first time here?”

That simple question was the beginning of a very pleasant conversation about some good Japanese restaurants in town.

This is a great question, because, unless you know the person in front of you has already been in a certain place, you can always ask it without sounding unnatural.

Follow-up questions

If the answer to this question is yes, you can then ask, “And do you like it here so far?”

If the other person says they’ve already been there, you can ask them “Nice! Perhaps you can help me choose something to eat?” In asking such a question, it opens the door for the other person to naturally, without even having to think, ask you what sort of things you like and don’t like — which keeps the conversation going.

2. Are you having fun?

This is another great conversation starter, because you can ask it to anyone, in any situation — and it can help you break the ice.

Also, after this question you can add anything related to the place or the situation. For example, after the other person replies, something you can say is, “I’ve always loved outdoor places like this, where you can meet up with your friends, eat something, and also play mini-golf.”

Follow-up questions

In case the other person tells you they’re not having fun, you can simply ask, “What kind of events do you prefer?” or “What would you prefer to be doing?”

If the other person tells you they’re having fun you can ask almost the same thing, “What is your favorite type of event/social gathering?”

3. Do you live here in town?

This is another question you can ask anyone — unless you already know where they live, of course.

Marta asked me this question as well the day we met. I told her I lived a few blocks away from John and then I asked her where she lived.

We spent at least twenty minutes talking about our neighborhoods. In other words, we had a pleasant conversation thanks to a simple “Do you live here in town?”

Follow-up questions

A good follow up question you can use after this conversation starter is, “Does your family live here in town too?”

If the other person doesn’t live in town, you can ask “Does your family live with you?” It’s a great way to keep the conversation going.

Another follow up question you can ask here is “Have you always lived here?”

Depending on the answer, you can also ask “Where did you live before?”

In short, asking someone about where they live and who they live with is an easy way to start a conversation.

4. How did you meet [the friend you have in common]?

If you and the other person have a friend in common, a great conversation starter is “How did you two meet?”

People are happy to tell how they met a friend or their partner, as it usually brings back good memories.

I remember when I asked Marta how she and John met, and she told me they first met when John hit her car with his scooter. I loved to listen to their anecdote and I know they’re always happy to tell that story when people ask them how they met.

Follow-up questions

A good way to keep the conversation going in this case is asking the other person to tell you more.

For example, something you can add is, “That’s sounds so funny, please tell me more.”

Some people might tell you they met on the job, since it’s not as uncommon as you might think, so in this case what you could ask here is, “Did you work in the same team/department?”

5. Are you working on anything interesting at the moment?

I tried this one not too long ago. In particular, a few months ago, I went out for dinner with a friend, Maria, and her cousin, Carla. It was the second time I met Carla. She had already told me she worked as a Human Resources Manager and that she loved her job.

So, I thought a good way to initiate a conversation with her was asking her about her job. I asked her if she was working on something exciting.

She told me about a Diversity and Inclusion project she was managing in her company. I could see she was happy to talk about that project as she had a sparkle in her eyes when she talked about it.

Asking something as simple as “Are you working on anything interesting at the moment?” is a great way to start an interesting conversation with virtually anyone, because, if you think about it, most people either work or study.

Follow-up questions

Some good follow up questions here are, “For how long have you been working on it?” and also “Was it your idea?”

6. What do you do in life?

This is a great question you can ask to someone you just met, just don’t make it the very first question as it is quite direct; but you can still ask it early on. This is also a great question to quickly get to know the person you are talking to.

As the previous question, it gives you the opportunity to have an interesting conversation about what the other person enjoys in their life, the only difference it’s this question is broader.

“What do you do?” is also a question that people love to ask in return so make sure you have an interesting response. Your life doesn’t have to be a bed of roses, and you can have problems; however, keep in mind it’s how you talk about the other person — and redirect the conversation to them — that will make you someone worth knowing — or avoiding!

Follow-up questions

A good follow up question you can ask people who work is “And would you like to grow in your organization/try to apply for a promotion?” It’s a good way to encourage someone to talk about their goals and ambitions.

If you’re talking to someone who studies you can ask, “After you graduate, do you plan to continue your studies/enroll in a Master Program/embark on a PhD journey?”

Another great way to keep the conversation going here is saying something as simple as, “Interesting, tell me more!” As explained in an article published in Psychology Today, when you actively listen to the other person and show a genuine interest in what they have to say, you‘ll have more opportunities to follow up on good talking points.

7. How was your week/day?

The best conversation starters are the ones that don’t sound forced or unnatural. And these are usually related to the context.

Asking “How was your day?” or “How was your week?” is one of the best ways to initiate an interaction with someone.

Most of times the answer is something along these lines, “Oh, it was pretty good, what about yours?” If you want to keep the conversation going you can explain how your day or week was, what you did, and ask a follow-up question; just don’t make the conversation all about you.

Follow-up questions

Here you can say something like “It’s good to hear your week was good, what did you do?”

In case the other person told you their day or week was not that great, you can simply add “I’m sorry to hear that, what happened? Do you want to talk about it?”

8. What’s your opinion about [choose the topic]?

Don’t choose something random, be specific and pick something recent you both know about. For example, “What’s your opinion on about what’s happening in Julia’s company? Did you hear they’re firing a lot of employees?”

Or “What do you think about the new mayor?”

Or “What do you think about Valerie and Mark breaking up?”

Also, as Francesca Gino explains in an article published on Scientific American, asking someone for their opinion can actually help you make a good impression.

As Gino puts it, “by asking someone to share their personal point of view, advice seekers stroke the advisor’s ego and can gain valuable insights.”

Follow-up questions

Here you can use follow up questions that encourage the other person to explain better what they think, for example, “Why?” or you can add something like, “Really? Tell me more.”

9. So, how did X go?

Two years ago, my company gave me the opportunity to travel to Seattle to attend a Diversity and Inclusion conference. Before traveling, I told a group of friends about this opportunity.

When I came back from Seattle, I saw my friends in a bar, and one of them, Charlotte, asked me, “So, how did the conference go? Did you like Seattle?”

So, I told her a bit about the amazing experience I had. Then she told me about a time she traveled to Hong Kong for business. It was a pleasant conversation, which lasted around one hour. Not bad!

Simply asking “How did it go?” is always a good way to initiate a conversation, as the other person will probably have something to say. And you can keep the conversation going by asking follow-up questions, or making comparisons to what you have done.

Follow-up questions

A good follow up question in this case is, “How many people were there?”

Also, another good idea is to ask, “When’s the next one and is it anywhere exciting?”

10. Have you talked to [name of a friend in common] recently?

This is a great question you can ask if you and the person you’re talking to have a friend in common. If you have more than one friend in common, then it will be difficult to run out of conversation topics.

I use this one frequently, as it makes it particularly easy to keep a conversation going.

Follow-up questions

If the other person hasn’t heard from your friend in common, you can ask them, “When was the last time you saw them/talked to them?”

If the other person did hear from your friend, you can ask other follow-up questions, such as, “How are they doing?” and “How long have you known them?”

11. I like your dress/bracelet/earrings/shoes, where did you buy them?

This usually works great between women. However, it can work pretty well between men as well.

For example, you can compliment a guy for their shoes for example. Or for their shirt. Or even for their phone or their watch.

Follow-up questions

Some good follow-up questions here are:

  • “Cool! Do you buy often from that shop/website?”
  • “Do you like watches/bags/shoes in general?”
  • “Can you recommend me a good shop where I can find a nice watch?”

12. How’s your salad/tacos/soup?

If you’re at a restaurant, a great question you can ask the other person is if they like what they’re eating in that moment.

It’s a very spontaneous question and it doesn’t sound forced.

You can also ask them if they like what they’re drinking.

Follow-up questions

A good follow-up question here would be, “Is that your favorite dish?”

Or, “Do you often order it?”

If they answer they don’t like what they’re eating or drinking, you can ask, “So, what is your favorite food/drink?”

Or, “What would you prefer to be eating/drinking?”

Final Thoughts

You don’t need a list of one hundred questions to be a good conversationalist.

Knowing a few good conversation starters and using them properly can help you get to know other people, better connect with them, and, in many situations, prevent awkward silence.

However, the best way to have pleasant conversations is to choose questions that are related to the setting you are in and don’t sound forced, and to combine them with follow-up questions that show you are interested in what others has to say.

Also, as Susan Krauss Whitbourne Ph.D. explains in Psychology Today,

“Sometimes it’s also important to note whether the other person would like to break off the conversation. To be a better conversation partner, you sometimes need to know when to close as well as to open.”

Article originally published in The Truly Charming

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