How To Keep A Conversation Going: 10 Tips For Texting, Dates & More

Originally published @ MindBodyGreen

By Sarah Regan

- Content and imagery reposted with permission -

No one likes an awkward pause in the middle of a conversation. We’ve all been there, and if chatting it up isn’t your strong suit, you may cringe at just the thought. Keeping conversations going can be a challenge, especially over text, or if you’re just starting to get to know someone. So, we asked relationship experts to answer all our questions around conversations, from how to start them to how to keep them going.

Getting the conversation started.

Conversations are going to look different depending on who you’re talking to and how close you are, but generally speaking, it’s always good to have an idea of why you want to have the conversation in the first place.

“Get clear about your own motives for starting the conversation,” couples’ therapist Alicia Muñoz, LPC, explains to mbg. “Are you motivated by pure curiosity? A desire to get to know someone better? A desire to build a stronger friendship? Do you have a specific goal in mind […] like a job interview?”

When you’re clear on your motive, she says, you can be open about it. People will naturally wonder why you’re striking up a conversation, “and being clear about it from the start creates trust,” she says. For example, if you were reaching out to a CEO on LinkedIn, you can explain from the get-go that you hope to work together. Or if you’re on a dating app, simply telling someone you’re interested in getting to know them can go a long way.

“Being upfront with people about your motives for starting conversations may feel vulnerable,” Muñoz adds, “but others often experience it as clarifying and refreshing. It fosters a genuine connection.”

Tips to keep things going:

1. Get curious.

Try to display genuine curiosity in the person you’re talking with. Licensed marriage and family therapist Holly Richmond, Ph.D., LMFT, CST, tells mbg, “I’m curious” is one of her favorite phrases. Think questions like “I’m curious about your…” or “I’m curious what you think about…” etc.

“People love to talk about themselves, and that ‘I’m curious’ question isn’t a judgment on your part,” Richmond says, “so there’s nothing the other person could get defensive about.”

As Muñoz adds, “Allow another person to experience your curiosity and interest in them. Let go of your agenda.”

2. Find common ground.

One of the quickest ways to start bonding with someone new is by finding common ground. “If there’s a moment to find synergy with a person,” Richmond suggests, “meaning shared likes and beliefs, that’s always a good way to go.”

It’s worth noting here that certain topics like politics, religion, and other potentially controversial subjects can lead to tension if you don’t already know where a person stands. If you want to avoid potential disagreements, you may wish to avoid such subjects. On the other hand, taking the risk to dive into these tougher topics may pay off if you find you have more in common than not.

3. Make sure it’s a good time to talk.

Sometimes people may not be the most forthcoming in conversation, and in some cases, this can be because it’s simply not a good time to talk. “If someone doesn’t seem to want to engage in a conversation with you,” Muñoz explains, “you could ask them directly, ‘Is this a bad time to talk? I want to connect with you, but I also want to respect this might not be a good time for you.'” This opens up the door for them to let you know where they’re at, and you should be able to gauge whether they’re interested.

4. Listen intently.

Really show you’re engaged and interested in what this person has to say. Not only will this make them feel good, but active listening can help strengthen all your relationships.

You can even practice with friends to improve your listening skills. A good rule of thumb for being a better listener: Don’t worry so much about what you want to say next. Just pay attention to what the person is saying.

“People generally open up more when they’re being seen, heard, noticed, and listened to in the little details of who they are and how they express themselves,” Muñoz says.

5. Ask open-ended questions.

Give people a chance to answer open-ended questions rather than giving straight yeses or nos. This is also another way of showing curiosity. As Muñoz notes, “Great interviewers know how to make people feel special by being genuinely fascinated by other people. Ask open-ended questions.”

As you listen, “notice their response without jumping automatically back to yourself, your experience, your interpretations of what they said,” she adds.

Tips for in-person conversations:

Pull from context clues. As you listen to someone talking, Muñoz suggests trying to “notice someone’s jewelry, the logo on their T-shirt, their overall energy level, their sense of humor, their way of expressing themselves, and celebrate that.”
Build on compliments. Just as people love to talk about themselves when you give them the opportunity, “People also love compliments,” Richmond notes. Finding something to compliment, whether it be something they’re wearing, or something more personal like their overall energy, can help the person soften and open up. You can combine this with tip No. 1, a question like, “I’m so curious where you got that fantastic bag,” Richmond offers as an example.
Have good eye contact and body language. Body language is essential. People can easily pick up on when a conversation has run its course by the way we position our bodies, how much eye contact we’re making, and our tone of voice. “Really make sure you’re looking the person in the eye, your body is facing them, and your arms aren’t crossed,” Richmond says.

Tips for texting conversations:

Don’t fret if they’re not the best texter. Texting isn’t for everyone, and it’s easy to overthink short replies and delayed response time. Whoever you’re texting could also be busy and not in a place where they can be totally engaged with their device. You can always ask whether it’s a good time, or if they’d rather talk on the phone or meet up IRL. “If a person answers in a monosyllable, don’t give up,” Muñoz says. “Keep attending to them. Maintain a warm, open stance. Don’t let your own insecurities break the connection.”

Be direct. One downfall of texting is the chance for things to get lost in translation. Your best bet is to be direct. “In texts,” Muñoz explains, “it’s important to spell things out that might otherwise be communicated in someone’s tone of voice or body language.” For example, you could say, “I’ve been thinking about you and wondering how you’re doing. I’d love to hear anything you want to share!” she adds.

Use emoji. OK, emoji aren’t for everyone. But if you want to communicate your message clearly and directly, one way to do so is through emoji—especially if we’re talking about messaging someone on a dating app. Research shows people who use emoji actually have more first dates, and it has everything to do with the way we respond to those little facial expressions when we can’t actually see the visual cues from whom we’re talking with otherwise. They fill in those gaps, so give ’em a try!

Specific topics and questions:

1. Their upbringing

It goes without saying that our childhood shapes us into who we become in so many ways. Basic questions about where someone grew up can tell you a lot about a person and is also a good chance to find out where the two of you may share similarities (or differences).

Some questions to ask:

  • Where did you grow up? What was it like?
  • Did you like growing up there?
  • What do you think is the best thing about your hometown?
  • Would you ever move back home? (Or if they live there, do they want to move?)
  • Where are your favorite places in town?
2. Weather and seasons

Yes, this might be considered small talk, but when in doubt, dealing with the weather is a universal experience, and everyone has something to say about it. There’s a reason it always comes up! Plus, someone’s thoughts on the weather can tell you what they like as far as the seasons and seasonal activities, what kind of day they’re having, etc.

Some questions to ask:

  • Do you like rainy days, or do you find them kind of drab?
  • What’s your favorite season and why?
  • What are your favorite things to do in fall, winter, etc.?
  • What does a day of perfect weather look like to you?
  • If you could skip any season, which would it be?
3. Hobbies and interests

Who doesn’t love to talk about what they’re passionate about? Getting curious about someone’s hobbies and interests shows you want to understand them, and you can also try to find some common ground here. Maybe you notice they posted a picture skiing or a newly completed art project, so you ask them about that. People are usually happy to share the things that bring them joy.

Some questions to ask:

  • What’s your favorite way to spend your free time?
  • What’s one topic you want to know everything about?
  • Is there a particular hobby you’ve been dying to pick up?
  • What’s the last internet rabbit-hole you went down?
  • Did you have any hobbies as a kid you’d like to pick up again?
4. Books, music, TV shows, and movies

At least one of these forms of media is likely a significant part of someone’s life. People get super passionate about their favorite musical artists, TV series, and so on, so ask them about it! You may find you both love the Lord of the Rings series, or you’re both big fans of classic rock.

Some questions to ask:

  • What kind of music do you like to listen to?
  • If you could live in any TV show’s or movie’s universe, which would it be?
  • Do you have an all-time favorite book or author?
  • What’s the best concert you’ve ever been to?
  • Who’s your favorite fictional character of all time?
5. School and work

Asking about school or work is bound to come up as you’re getting to know someone. It’s always good to know what someone’s goals are, what they’re studying or have studied, and how that ties into their story. Just pay attention here if the tone shifts when you bring these things up, as school and work can be sources of stress. If it seems like they don’t want to talk about it, you can always redirect the conversation:

  • What did you go to school for, and what made you decide that?
  • Did you ever think you would be a [insert career], or did you want to be something else growing up?
  • What’s your biggest professional goal right now?
  • What’s your favorite class right now? (Or if they’re working, what is their favorite part about their job?)
  • Do you ever feel called to try something else career-wise, or are you happy with where you’re at?

The bottom line.

Conversations aren’t everyone’s forte, and that’s OK. At the end of the day, showing you are actively listening, offering nonjudgmental and open questions, and simply being kind and forthcoming will never steer you wrong when chatting with someone, whether they’re a new friend or an old one. Try practicing with people you’re close with to strengthen your conversational skills. And when in doubt, a compliment never hurts.


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