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15 conversation prompts to connect on a deeper level without making it weird

These "reflective" topics are meaningful but not overly personal.

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It's not always easy to have good conversations in groups.

When family and friends gather together, conversations can go a few ways. If you’re genuinely close and used to sharing openly, conversation may flow naturally with no need for assistance. If you’re getting together with people you rarely see, don’t know very well, or struggle to connect with, however, conversations can feel mundane, stilted or awkward. Even with family, a 50-year-old trying to talk to a 15-year-old extended relative can be difficult without knowing what questions to ask.

Whether we’re getting together with people we know or people we are meeting for the first time, it’s nice to be able to go a little deeper than talking about the weather or pop culture. Politics is a minefield, now more than ever, and not everyone wants to share the nitty gritty details of their personal lives, so it can be hard to figure out how to have meaningful conversations without making it weird.

Ordinary & Happy offers a list of “reflective topics” that can help improve conversations with anyone of any age. Here are some examples of questions based on their suggestions and some reasons they're so effective.

Looking back

What’s something you learned this past year?

Who was an influential person in your life last year?

What’s something you accomplished this year that surprised you?

The good thing about looking back over the past year is that the experiences are fairly fresh. A year is a good amount of time to think about because it’s short enough to not be overwhelming but long enough to have had some interesting experiences and learnings.

Looking again

What’s something you rediscovered a love for?

What’s something or someone you’ve reconnected after a long time?

What’s a place you’ve visited that you really enjoyed?

A twist on reflection, adding a “re” element by asking someone about something they might have forgotten about or disconnected from but found again can be a fun way to think about the previous year a little bit differently. And of course, places we’ve enjoyed visiting is always a solid topic.

Looking ahead

What’s something you want to improve on next year?

What’s a goal you have for next year?

What’s something you’re looking forward to next year?

It can be a little tricky to ask people about the future, especially young people who often feel a lot of pressure to have their futures figured out. But on a personal level, we all have things we’re looking forward to as well as intentions for our future, even if we don’t know how it’s all going to play out.

Looking inside

How has your perception of time changed?

Have your values shifted or changed and what prompted it?

What’s something you learned about yourself this year?

These questions offer a way to get to know someone without asking about too-personal topics. Values might be considered personal, but there are a lot of ways to ask people about how the way they see the world or themselves has changed.

man and woman talking over coffeeThese prompts can work in a group or one-on-one conversations.Photo credit: Canva

Looking at being human

What do you believe is a key to good communication?

What do you believe is one of the best ways to build trust?

What do you believe the last year taught you about life?

Broadening the questions to more general human experiences rather than focusing them on an individual is a good way to pivot if people seem to feel uncomfortable talking about themselves. The adage “People love to talk about themselves” isn’t always true, but most people will weigh in on a light philosophical question like “What do you think makes someone a good friend?” or “What do you think the world needs more of?”

Anyone can come up with these kinds of reflective questions. A few tips to keep in mind, though:

- Try to avoid words like “favorite” or “best” unless you preface it with “one of.” You don’t want to force people to sort through their thoughts and put them in a particular order. Some people may have one favorite place or memory, but more often than not there are many things that could compete for that title and trying to narrow down one makes people freeze up.

- Stick to universal human experiences. We’ve all discovering things about ourselves and the world all the time, but we’re not all into the same things. “What’s a place that makes you feel peaceful?” works better than “What’s your favorite place to vacation?” Keep questions broad and focused on human characteristics instead of niche experiences people may or may not have had.

- Put questions into your own words. You might not say, "What's one thing you learned this year?" For you, it might be, "Hey, tell me about an interesting learning experience you had this year. What stands out to you?" The more natural the question in your own voice, the better. It's the topic that matters, not the wording.

Happy conversating!

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Family

Forget "How's school going?" Try these questions instead to get shy teens talking.

If talking to your young relatives feels like pulling teeth, here are some questions that can help them open up.

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Teens might seem uncomfortable at first, but you can help make them feel at ease.

Have you ever seen someone who seems to have a knack for talking with teens and wondered what their secret was? Sometimes it seems like getting young people to offer anything other than monosyllabic answers to questions is like pulling teeth. Maybe they're shy or self-conscious, or maybe the questions adults tend to ask aren't very effective at getting them to open up, but when you're gathering with family for the holidays and want to spend time getting to know your teenage relatives, it can be tough when the conversation feels awkward or forced.

Shyness is real and self-consciousness often comes with adolescence, so there's not a whole lot we can do about those things, but there are ways to engage young people that are more likely to result in a real conversation. When our "How's school going?" gets a "fine" or a "good," we know we need some better questions, but it's not always easy to think of those on the spot.

That's where some helpful guidance from Raising Teens Today comes in super handy.

woman talking with a teenMost teens actually like to talk if you ask the right questions.Photo credit: Canva

"Let me clue you in on a little secret... teenagers LOVE to talk," writes Nancy Reynolds, the mom behind the Raising Teens Today website. "Sounds crazy, right? I promise, you can get the quietest teen on the planet chatting simply by asking them questions that make them feel comfortable and want to share their world with you."

First, she offers some points to keep in mind as you chat with teens specifically:

- Steer clear of subjects that can put them on the defensive or make them feel awkward or inferior, including their grades, changing bodies, or whether they have a boyfriend or girlfriend, for instance.

- Keep it light. Don't get into heavy subjects. Teens have a lot on their shoulders already. Laugh a little. Have fun.

- Ask questions that will get them talking. Ask about their friends, things they love doing, books or sports or hobbies they love, their passions or dreams.

- Don't ask "loaded" questions such as, "You ARE going to college, right?'" Or, "Do you EVER look up from your phone?" Nothing will make a teenager clam up faster.

- Teenagers are young adults. Treat them as such. Show respect.

- Just be authentic. Teens can spot a fake from afar. If you're genuinely interested in their life and they sense you truly care, they'll open their heart... and when they do, it's such a gift.

The mom of three teens also gave some suggestions for what to ask in place of the standard questions we tend to use. An "ask this, not that" of talking to young people.

These questions go beyond the standard ones adults often ask or provide a twist on the classics that put young people at ease:

"What's the most interesting thing you've learned this year?"

"What do you enjoy doing with your friends?"

"It won't be long before you graduate. I'm so anxious to hear your plans!"

"I'd love to hear what you've been up to if you feel like chatting."

"What's your favorite thing to do when you're not in school?"

"What's the coolest thing you've seen online recently?"

"What's the one thing you're most looking forward to next year?"

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Don't bombard them—it's not an interrogation–but try out a couple and see how they go. It's important to note that some kids might be flummoxed by questions that require them to choose "the one" or "the most" or "favorite," so you can always alter those kinds of questions to be more open-ended, like this:

"What's something you like to do when you're not in school?"

"What classes are you finding interesting or challenging?"

"Have you read or seen anything you really enjoyed lately?"

"What are you looking forward to after the holidays?"

You can also think about meeting kids and teens where they are by being curious about the reality of their lives—but in a way that isn't overly intrusive or judgmental. For instance, instead of only asking what their favorite subject is in school, ask what their least favorite subject is as well. That will almost surely get them talking. Instead of scoffing about them being on their phones, ask them what social media sites they like the most and why they prefer them to others. You can also ask them their opinions about things like whether they prefer reading paper or digital books, whether they prefer lectures or small group discussions, whether they feel like they learn better from listening, watching or doing. Questions like these don't make them feel like they're being quizzed or tested, because there aren't any right or wrong or even preferable answers.

If you do ask about a "favorite," make it something that they can easily choose a favorite from and something that can lead to further conversation. For instance, "Do you have a favorite teacher?" followed up by "What do you like about them and their class?" That can lead to a nice back and forth about what makes a teacher effective, what makes a class interesting or boring, and what your own experiences with good or bad teachers has been.

Another way to engage teens at your family gatherings is to ask them to help with something in the kitchen. Giving them something helpful to do takes the social spotlight off of them and creates more opportunity for small connections, making more meaningful conversations feel like the natural next step.

teens helping bake in the kitchenGetting them in the kitchen can help with conversations.Photo credit: Canva

People are appreciating the tips offered, as connecting with young people can be a challenge for many adults.

"Where were these questions when I was younger?? How different would the conversation been?"

"🫶🏽 It’s all in the wording! Connections are so important."

"I love this!!! It can be a lot of work getting your teen to go to an adult gathering. It’s never helpful when they get there and end up feeling either judged or completely ignored. It only isolates them further when what they need more than anything is connection with adults."

"Thank you for this. My father will ask my 14 year old what she wants to do for college and I can see the anxiety build up in her. How about what do you like to do in your spare time? What are you proud of? What are you interested in?"

"I’m a grandparent and this is just what I was looking for to open a positive interaction during family events. Thanks again!! 🙌"

It's definitely worth trying some of these out over the holidays.

You can follow Raising Teens Today on Facebook, Instagram and raisingteenstoday.com.

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Health

Stanford communications expert says this is the best way to start a conversation

It works for parties, work and relationships.

via Canva/Photos

Two coworkers making small talk.

One thing that makes people anxious when they have to make small talk is that they feel compelled to be interesting and put on a show. They think they have to wow the person they’re talking to with their wit, insights and stories.

However, Matt Abrahams, a Stanford communications expert and host of the "Think Fast, Talk Smart" podcast, says that people shouldn’t feel pressured to be interesting at all.

“A lot of us put tremendous pressure on ourselves to be interesting,” Abrahams told Inc. “We want to say exciting, valuable, relevant stuff, and it’s the wrong mindset. I think many of us see small talk as a tennis match where the goal is to get the ball over the net and score. I think we should see it more like hacky sack. The goal is to serve it to the person so they get and can serve it back to you. Success is when you all work together.”

Simply put, “the goal is to be interested, not interesting,” Abrahams said, paraphrasing matchmaker and author Rachel Greenwald.

“It’s about curiosity,” Abrahams says. “Starting with questions, observing things in context, bringing up relevant information. So, if you’re at a corporate event, you could talk about the keynote speech. If you’re at a cocktail party, you could talk about what’s happening in the room.” Most importantly, he says, “avoid the doom loops of ‘Hi, how are you?’ ‘Fine, how are you?’ And then you’re nowhere better off.”

It all boils down to the idea that people love being heard and asked questions. People often say that when they meet someone who listens well, they are an interesting person. This also points to the fact that we’re so used to the person we’re talking to just waiting for a chance to speak that it is refreshing to be with someone who is all ears.

Patti DeNucci, known as the Intentional Networker, believes that Dale Carnegie coined the phrase in “How to Make Friends and Influence People,” where he shares his axiom: “To be interesting, be interested.” She adds that Carnegie believes that people should be genuinely interested in others but also have a lot of interests.

DeNucci says we should strive for “living a good life,” which includes interests in cultural, academic, and travel pursuits. “After all, when we’re interested in many things, there’s a better chance we will be more equipped to take an interest in what others have to say,” DeNucci says. “And, in turn, we’ll also have something interesting to add to the conversation to keep it going, expanding, deepening.”



Carnegie’s thoughts on the power of listening were proven in a 2016 study that on sales calls, that did an excellent job of quantifying the amount we should speak versus listening during a conversation. A marketing director at Gong.io analyzed 25,537 sales calls and found that the interactions where the salesperson listened 57% of the time and talked 43% of the time had the highest sales yield.

This is known as the 43:57 rule.

Hopefully, these insights will make everyone who feels nervous about going to their next party feel a bit more confident walking into a room, knowing they’ll be a big hit simply by being genuinely interested in people. It also reminds the talkative bunch out there that people will probably like you more if you keep your mouth shut.

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Communication coach shares 7 ways to get out of a conversation without being awkward or rude

For many folks, figuring out how to end a conversation is even harder than starting one.

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It's not always easy to ease your way out of a conversation.

Have you ever found yourself in a conversation you don't really want to be in anymore? Maybe the conversation's gone on too long or the person has you cornered or you just genuinely don't have time to keep talking with them?

For some people, figuring out how to end a conversation without being rude or making it awkward is a challenge. Social etiquette is not always intuitive, and while some seem to to effortlessly navigate all kinds of social situations, many of us struggle with certain aspects of socializing. Most people might assume that starting a conversation is the hardest thing, but ending one can be equally or more challenging. You can't just suddenly say, "Okay, bye," without warning, but that transition between conversing and leaving doesn't always happen naturally.

Thankfully, communication coach Alexander Lyon has offered 7 clear ways to wrap up a conversation politely to help those who need a little help.

- YouTubewww.youtube.com

Here's what he suggests:

1. End on your turn

Every conversation is a back-and-forth, with people taking turns talking. Interrupting the other person to say you need to go can come across as rude, so make sure you plan to end the conversation when you're already talking. "All the rest of the tips flow from this concept," Lyon says.

2. State a time limit

This can come at any point in the conversation. If you're talking to someone you know might drag it out, it might be good to place it at the beginning of the conversation: "Hey Steve, I've got about five minutes. What's up?" That way they know the conversation time is going to be limited from the get go. You can also drop the time when you're ready to wrap up: "I only have one minute before I have to go, so let me finish with this thought." That way the person knows the conversation is coming to a close.

3. Start packing up

Those who feel awkward about ending a conversation might feel like it's awkward to start gathering your things before the conversation is concluded. But it's a normal thing to signal through behavior, and packing up signals to the other person that you're ready to end the conversation.

"You start putting things in your bag. You get your keys out. You put your coat on. This shows them oh something's changing here. Alex is about to leave." Lyon says these are non-verbal actions are called leave-taking behaviors. "This is what we all do naturally when we're about to go and so these cues are really known and powerful to most people. They will pick up on them," he says.

4. Say you've gotta go

This might seem obvious, but Lyon assures us that that's exactly why it works. "You have to use phrases that they're used to hearing like 'I've gotta run,' 'I've got to get going,'" he says. "Those are phrases that signal, once again, that you're going to go. A lot of times people even feel like just saying that feels rude. But I assure you these are just common phrases that, wrapped into the other tips, they're going to understand that this means you're going to go."


via GIPHY

5. Tell them what's next

Share what you're going to be doing after the conversation. "If you say things like, 'I have a meeting to go to' or 'I have some projects that I've got to get back on' or 'I'm a little behind on some work,' then they'll know that, 'Oh he's not just abandoning the conversation because he doesn't like me. He's going because he has something else to do,'" explains Lyon. You don't have to be super specific, just clear and concise.

6. Insert polite pleasantries

This is where you say things like, "It was so great catching up!" or "I hope we get to chat again soon," or "I'm so happy we got a chance to talk," to indicate that it's time to move on but you've enjoyed the conversation. Lyon shares that these kinds of statements signal to the person that the conversation is coming to a close and are such a normal part of interactions that the person will understand what they mean.

7. Apologize and repeat any of the above, if necessary

If the person is really holding on and not taking the hint, say something like, "So sorry, I really have to get going, but it was so lovely to chat with you," or something similar. "A lot of times people need that little extra reinforcement toward the end," Lyon says. He says you don't want to drag the apology or make a big deal out of it—just a quick, "Sorry, but I gotta go," or "I apologize, but I'm running late," will do. "It doesn't mean you've actually done something wrong that you need to apologize for. It's just a way once again to signal that you're trying to be respectful to that person," Lyon explains.

Even if some of these tips feel awkward or rude, Lyon assures us that they aren't. People with social anxieties can often overthink interactions, so having such reassurances can be helpful. Courtesy in conversation is one of the ways we maintain social connections, so learning how to politely end a conversation is a valuable skill.

You can follow Communication Coach Alexander Lyon on YouTube.

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