How to Keep Conversations Going When You Feel Stuck

Some people seem to instinctively know how to keep conversations going…and then there’s the rest of us. We ask friends to stick with us at parties, dread networking events, and repeat the same dull comments about how fast the year flew by. Then it gets even worse when we get home of all places! This is where we should be able to relax and open up, but we don’t. Instead, we sit side by side on the couch watching TV, head to bed, and doomscroll. But the reality is, we all have things to share: opinions, passions, funny memories, and dreams for the future. We just get stuck from time to time, or fall into the habit of silence. And our relationships start to suffer.

Luckily, the problem is fixable! Becoming a good conversationalist is actually something you can learn (it’s proven!), and we’ve got concrete steps you can take to get there. We did the research, and we can help you. Our tips will teach you what to talk about, how to keep a conversation going, and which deep conversation topics build emotional connection. Before you know it, you and your better half will be bantering for hours and sharing your hopes and dreams together. Learn how to transform your daily conversations from small talk to something way more meaningful.

Why conversations get stuck

There’s so many reasons we struggle to connect with others, even with the people we know and love best.  Here are just a few: 

We’re distracted

We’ve got screens everywhere and social media competing for our attention. Modern life isn’t easy. The economy is bad,  our jobs are stressful, and we’re bombarded by constant bad news from all around the globe. Honestly, our personal lives aren’t much easier. Each phase of life brings new stressors:

• Younger couples are struggling to build careers and afford housing
• Middle-aged couples care for children and elderly family members
• Mature partners have financial and physical wellness to consider. 

Who has time for thought-provoking questions with those serious subjects already on our minds?

Vulnerability feels risky

Even if we did dive into deep conversation topics, what would our partner think of us? Many of us are self-conscious around new people, which is understandable. But we hold back in our own relationships for more serious reasons. When we get vulnerable and open up, we risk the judgment of others, even people we love. If we admit our fears or insecurities, will our partner see us as weak? If we share an ambitious life goal, will it look unrealistic or even ridiculous? Sometimes it just seems simpler to keep things to ourselves.

We assume we already know people

Long-term relationships get comfortable...sometimes too comfortable. You know your other half inside and out (or at least you think you do). 

• You’re best buds with their friends and consider their family yours.
• You’ve seen the best and worst of their moods.  
• You known their Netflix password and the punchlines to all their cheesy jokes.
• You can practically read their mind, which means there’s no new things to talk about… right?

Actually, there’s always something new to talk about, and the truth is that you can always get better at talking, too. Conversation skills are like any skills: we can learn them, practice them, and improve at them daily. Charles Duhigg, author of Supercommunicators, says that great communicators are “made, not born.” Many of those he spoke to admitted they had been bad at communication earlier in their lives. According to Duhigg, if you learn techniques and “train yourself to pay attention,” you can improve connection through conversation.  

We fall into scripts and routines

Ever find yourself part of this routine?

How are you, how was your day?

Fine. Long. Tiring. Yours?

It was good.

Good.  What do you want to do for dinner?

I don't know. I could make something here or we could go out.

Note: there is absolutely nothing wrong with these conversations. In fact, these little exchanges are normal and necessary for getting through busy days and making plans. The problem starts when the majority of your conversations become logistical, predictable, or surface level. When that happens, it feels like there's nothing new to say.

This can happen in every kind of relationship.

• Couples talk mostly about bills, chores, and schedules.
• People who are dating get stuck asking the same basic questions about work, hometowns, and weekend plans.
• Friends send memes but rarely talk about what is actually going on.
• Families fall into familiar roles and old stories, even when everyone has changed.

The conversation goes on auto-pilot.

A better question can interrupt the routine. For example, instead of asking, “How was your day?” you might ask, “What part of today made you the happiest?” Or instead of, “What’s new?” you might ask, “What’s something you’ve been thinking about lately but haven’t said out loud?”

How to keep a conversation going

So experts have told us we can get better at conversation. But how can we do it, exactly? If you’re one of the many people asking yourself, “Why can’t I keep a conversation going?”, here’s a list of key principles to help you improve.

1. Be interested, not interesting

In the family sitcom The Middle, Frankie Heck wants her unsocial husband to improve his conversation skills. The problem? Mike Heck is burned out from working long days at a quarry and raising three children. His interests are limited to the Indiana Colts and beer. He has very few things to talk about, and no idea how to continue a conversation. So his wife suggests he use a great opening line. Here it is: 

“I don't know much about that, but I'd be interested in hearing what you have to say.”

He tries the line at his neighborhood barbecue, and the results are incredible. Neighbor after neighbor opens up about their hobbies, their travels, even their relationship troubles. In fact, one married neighbor finds herself attracted to Mike Heck’s listening skills and comes on to him!

What’s the lesson here? 
That we can seduce people with our listening skills? 
(Well, yes!)

But more than that. You don’t have to be a rocket scientist with killer quips and endless anecdotes to have a great conversation. You just have to give the other person the chance to share their interests.

And this skill is not just a party trick for the neighborhood barbecue. In fact, it’s key for long-term relationships. Todd Kashdan of George Mason University conducted a study on how people felt about joining in “increasingly intimate conversations.” He said: “Being interested is more important in cultivating a relationship and maintaining a relationship than being interesting; that’s what gets the dialogue going.”

That means sparking emotional intimacy your partner can start with just one question. Why not ask it tonight?

2. Pay attention before planning your response

Okay, so you’ve asked your partner a question. You’ve opened up space for them to share their memories, experiences, or hopes. (And science has proven that people love this opportunity!). What do you do next? Well, you want to keep the conversation going – ideally, for a lifetime!—so you line up the next question, right?

Wrong. “If you’re thinking about what you’re going to say next, you’re not really listening,” life coach Jenn Gruber observed. What your partner says will naturally lead you to the next question. It may sound counterintuitive coming from us. (After all, our passion is creating thoughtful questions to bring couples closer together!) But we’d rather see couples connect meaningfully over one prompt, take the time to listen to each other, and see where it leads them. There’s a reason we use the phrase “pay attention” in English: our attention has value.  In long-term relationships, it can be priceless.

3. Ask thoughtful follow-up questions

Conversation isn’t a checklist, and Deeply certainly isn’t, either! When your partner finally opens up, don’t shut the door. Instead, follow up with thought-provoking questions based on what they’ve shared. Depending on the conversation, follow-up questions could include:

• Why do you think you’ve never forgotten that?
• How did you feel at that moment? Have you ever had a similar experience?
• And how did your dad/sister/roommate react to that?
• Do you think you would react differently today?
• What inspired you to choose that life goal?
• Do you know anyone who’s already accomplished that?

Follow-up questions show that you care and you’re curious to know more. In long-term relationships, they show both of you that you can still surprise each other. 

4. Share something real in return

After the follow-up questions, it’s your turn to contribute. After all, great conversations are all about give and take. Plus, your partner might feel a bit anxious after opening up and being vulnerable about their private feelings, or lofty dreams. So, to make them feel comfortable, find common ground.  

Reassure your partner that they’re definitely not the only one with embarrassing middle school memories, pet peeves about their colleagues, or a wild daydream about winning the lotto! 

Tell them that you relate and show it by sharing a story of your own: silly, sweet, embarrassing, and at least a little bit vulnerable. This moment of emotional connection will bring you closer together and end the exchange on a positive note, which means that both of you will look forward to your next deep conversation.  

 
Conversation Starters for Different Relationships

Now you know the key steps to having a successful deep conversation. But why does having them matter so much? Well, beyond the fact that surface-level conversations run out pretty quickly, there is a big difference between small talk and more meaningful exchanges.
 
Amit Kumar of the University of Texas at Austin studied how people participate in different types of conversations. Findings show that even people who are hesitant to answer thought-provoking questions and share personal feelings end up enjoying it. Kumar thought those findings could “encourage people to dig a little bit deeper” and get out of their conversational comfort zones.

Here's just a few ways you can do this within your relationships: 

For couples

If you're part of a couple, ask your partner questions that invite emotional intimacy, appreciation, memories, and future dreams.

For early dating

Just started seeing someone new? Offer questions that feel playful, curious, and revealing. (The key is to avoid becoming too intense too soon!)

For friends and family

With your friends and loved ones, ask questions that open up stories, shared memories, values, humor, and life experiences.

How Deeply helps when you don't know what to ask

But our conversational comfort zones are so…. comfortable! True. And that’s why we’ve designed Deeply. Our thought-provoking questions bring people closer. We tailored our Couples Edition to partners in long-term relationships who want to improve their emotional intimacy in an enjoyable way. The low-pressure, fun design helps you get past the hump of, “What do we talk about?” 
 

What makes Deeply unique among conversation starter card decks? Ours is a digital, which means that Deeply is always accessible. It’s portable, modern, and curated, for meaningful conversation that goes wherever you do.

If you’ve ever asked yourself, “Why can’t I keep a conversation going?”, then Deeply is definitely for you. With our instant access, portable tool, you can train to become a better conversationalist today. 

Remember: even if you weren’t born with the gift of gab, you can learn to master the skills that bring people closer. 
 
Take the first simple step with Deeply, and ask your partner one new question tonight to begin the first of many great conversations.