26 Fun Conversation Starters For Long-Term Relationships

Nothing like your most embarrassing moments to lighten the mood.

by Carolyn Steber and Kristine Fellizar
Originally Published: 
 how to start a conversation with your boyfriend.
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Once you've been with your partner for a minute, it can sometimes feel like you've talked about everything. You've told your stories, you've shared your dreams, and you've muttered a few words about what you'd like to eat for dinner. Now, you feel like you literally have nothing creative, interesting, or important left to say — and the silence is deafening. So, what do you do next?

This moment can certainly be a turning point in a long-term relationship, but there is no need to fret — especially since the more you worry about coming up with something new to say, the harder it'll be. "Stop trying to talk about 'new' things," Dr. Josh Klapow, a clinical psychologist, tells Bustle. That strain “of trying to think of something new can easily take over the vibe of the conversation." It's totally OK to let topics come up naturally, to chat about the weather, or to simply sit quietly and enjoy each other's company.

It's also OK to talk about the same thing more than once. "If you have been with your partner for a while then you can absolutely revisit old topics," Klapow says. "The topics may not change, but your perspectives, your understanding of them, and how you see them as individuals and as a couple will."

Klapow says it's very natural to have ups and down in a long-term relationship, including moments of boredom, and that it's rarely a sign of a deeper problem. But there are ways to remedy it all the same. If you'd like to chat about fun things, here are a few ways to start up a conversation with your partner, even if it feels like you've already talked about everything.

1. Get Into A Healthy Debate

If it feels like your conversations have screeched to a halt, try stirring up a healthy debate. "Find a provocative quotation and discuss your separate interpretations," Dr. Marlene Caroselli, an author and speaker, tells Bustle. Or throw out a fun topic — like, "do you think aliens exist? — and discuss.

If you both agree, cool. But if you don't, it'll quickly turn into some fun banter. And who knows? You might even learn something new about each other.

2. Ask About Their Day

This is a conversation you can have every single day. So if you aren't already in the habit, consider sharing your highs and lows after you've spent time apart. How was work? What went well? What didn't?

As Christie Tcharkhoutian, LMFT, a licensed marriage and family therapist says, this simple discussion will deepen your connection, stay on the same page, and ultimately help you weather life's ups and downs as a couple.

3. Make Plans For The Future

When was the last time you checked in with each other about your future? If it's been a minute, talk about what you'd like to do in the next year, five years, etc., including where you want to travel, where you see your careers going, and so on.

"It’s fun to dream and get excited," Tcharkhoutian says. "It also can help bring you outside of the daily routine and rut," and ensure that you're working towards these things together.

4. Talk About The Past

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On the flip side, the past is also an untapped source for good stories. So, while you've likely covered the basics, try to delve deeper by sharing childhood secrets or telling old family stories.

"You may learn things you never knew before, like their favorite game to play, favorite place to visit, and even turn that into a surprise trip or fun date night," Anjani Amladi, MD, a board-certified adult psychiatrist, tells Bustle.

5. Play The Question Game

Have you ever played the question game? It's simple, since all it involves is (you guessed it!) asking each other questions. There is, however, a twist or two, Dan Munro, a confidence and relationship coach, tells Bustle.

"First, you must ask deep and dark questions — try to get the real secrets out of someone," he says. "Second, you must answer as honestly as possible. It's like truth or dare... without the dare part."

Of course, it's OK to say no and to keep secrets to yourself, if that's what you'd prefer to do. No one ever said you have to be a completely open book, just because you're in a relationship. But this game will help build a sense of closeness between you if you trust each other with a secret or two.

6. Tell Each Other Exactly How You Feel

If you can't shake the nagging feeling you've "run out of things to say," Munro says it's often a sign you're keeping your cards too close to your chest, and not letting each other in. So go ahead and get real.

Ask how your partner feels, right this moment. What would they like to work on in your relationship? What's bothering them? The more honest and open you are, the better your relationship will feel.

7. Share Random Thoughts

In the same vein, consider sharing "random" thoughts and emotions, even if they don't seem conversation-worthy. As Munro says, the "noise inside your head" can be quite interesting. And since it's always changing, you technically can't run out of things to say.

Of course, this doesn't mean blurting out hurtful things or talking just for the sake of talking. Instead, it's about pulling inspiration from your inner dialogue — your daydreams, thoughts, concerns, etc. Bring it all to the surface, and see where the conversation leads.

8. Talk About Physical Intimacy

This is a topic you should be chatting about regularly, to make sure you're both happy and on the same page. But it's also fun to share your fantasies, especially if you've never talked about them before.

So, talk about it: Are you both fulfilled? Do you want to try something new? It may feel awkward at first, but questions like these can spark a healthy convo that you've probably never had before.

9. Ask Them What They'd Change

If your partner could change one thing from their past, what would it be? What would they do differently, if they could go back in time?

"These questions let you know more about your partner, what they may regret, what inspires them, and what brings them happiness," Kimberly Hershenson, LCSW, a licensed therapist in New York City, tells Bustle

As a bonus, it'll help you make better decisions as a couple going forward. By knowing what your partner regrets, you can work together as a couple to ensure history doesn't repeat itself.

10. Talk About Regrets

Similarly, you can learn more about each other's pasts by chatting about regrets. "This is a 'deep' question not suited for light-hearted moments," Jonathan Bennett, a relationship and dating expert at Double Trust Dating, tells Bustle. "But, a person’s greatest regret in life can reveal a lot about them."

So, when the mood is right, share your biggest mistakes and missed opportunities with each other, and it might just open the door to some pretty heartfelt discussions. As Bennett says, "It can be a great way to be vulnerable with each other."

11. Chat About A New Hobby

Life can certainly feel monotonous when you're following the same schedule day in and day out. So make a point of shaking things up. "Find a new hobby to enjoy together," Stef Safran, a relationship expert, tells Bustle. "Cooking, working out — something you can do together."

Or, go out on your own for an evening. Part ways and visit friends, try a solo hobby, or simply spend some time alone. When you meet up again, you'll both have plenty to discuss.

12. Learn More About What Influences Them

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Ask about heroes, or people or things that influence your partner, including family members, favorite authors, political figures, etc. "This question can help you learn a lot more about your partner and the people who shaped their life," Bennett says. "You might gain a greater understanding of your partner’s values and choices."

13. Ask About Their Ideal Career

It's easy to get stuck in a career field for the paycheck, instead of for the passion. So ask what would your partner do if money was no object?

"Most people rarely pursue their dream job," Bennett says. "Your partner might have a dream career that you never knew about, like musician, professional athlete, or dancer." Learning more will help you see each other with fresh eyes.

From there, consider ways to support each other in taking steps towards a more ideal job, if possible. If either of you feels stuck in life or in your relationship, going back to school or making a career change might be just what you need to feel inspired again.

14. Make Each Other Laugh

Another way to break out of a conversation rut is by trying to make each other laugh, Risa Williams, LMFT, a therapist and life coach, tells Bustle. When you've succumb to boredom, or are in a stodgy routine, it's easy to just go through the motions without keeping an eye out for funny moments. But they're always there.

Make a point of bringing levity back into your day by telling funny stories, joking around with each other, and making witty observations. Chances are you did this all the time when you first started dating, so bring it back!

15. Admit To Embarrassing Moments

Another way to make each other laugh? Fess up to your embarrassing moments, whether they happened five minutes ago, or five years ago, Leina Rodriguez, LMFT, a licensed marriage and family therapist, tells Bustle.

Not only is it fun to lightly rib each other after a screw-up, Rodriguez says "it can also help you learn how your partner overcomes [their mistakes], or if they have a hard time letting go."

16. Choose A Conversation Starter

When in doubt, turn to the trusty internet for some couple-y questions, as a way of finding new things to talk about, Sarit Fassazadeh, LCSW, a licensed clinical social worker, tells Bustle.

Start with the 36 questions that lead to love, from The New York Times. "Maybe pick a question or two a day," she says, "and really explore them together."

You might also turn it into ritual to answer one night a week while eating dinner, as a way of checking in and reconnecting. "There is always more to learn about a person," Fassazadeh says. "It's just finding the right questions to ask."

17. Play A Thought-Provoking Game

There's nothing quite like a rousing game of Trivial Pursuit — or another game that gets your brain’s gears turning — so dust yours off and get to playing. "These types of bizarre and random questions can spur new and stimulating conversation," Ashley L. Annestedt, LCSW, a licensed clinical social worker, tells Bustle, while also helping you step out of a boring routine. Because really, who doesn't love game night?

18. Talk About Books & Movies

How often do you watch a show together, then turn off the TV and go your separate ways? If you answered "always," you're missing out on a prime opportunity to talk about what you just watched, Alysha Perlman, LCSW, a licensed clinical social worker, tells Bustle.

"Reading a book together or watching a movie and then having mindful conversations surrounding your thoughts about it can be a great way to connect and talk about something other than the day-to-day," she says.

19. Get Real About Money

Since couples historically dislike talking about money, chances are you haven't discussed finances lately — if at all. So if you're at a loss for what to talk about, this might be your ticket.

"The thing about money is that it’s the type of conversation you can keep having and it never gets stale, especially as you begin reaching new milestones in your life," Andrea Woroch, a finance and budgeting expert, tells Bustle. "Topics can include everything from discussing how to cut back on monthly bills, to negotiating a raise at work, to shopping around for the best deal on a new piece of furniture."

In fact, she recommends setting monthly "budgeting dates" to check-in and see how you're both feeling about things you split or share as a couple, like a joint savings account or bills.

20. Learn To Be OK With Silence

All of that said, don't feel pressured to talk 24/7, if you (or your partner) don't want to. "Oftentimes we feel we must fill all of our space with entertaining chatter," Stacey Greene, relationship expert, and author tells Bustle. "Truly, once in a while it feels great to just stare, gaze, smile, cuddle, hold hands, etc." So if that's what's happening, go with the flow.

There will be moments of silence in your relationship, as well as moments of great conversation and deeper discussions. Find a balance between the three, don't force it, and chances are you'll never run out of things to say.

21. Talk About The Kind Of Parents You Want To Be

If you’re at a point in your relationship where you’ve determined you both want kids, make it a topic of conversation. Lisa Concepcion, dating and relationship strategist, suggests asking open-ended questions such as: Have your views changed about parenting? Now that we’ve been together for five years, what makes you sure we’ll be good parents? What things do you want to experience before becoming a parent? What kinds of parents annoy you? What kind of parent do you want to be? Even if you know the answer to a few of these, it never hurts to ask anyway. As Concepcion says, “When people are truly committed to growing together in a relationship they never presume they know everything there is to know about their partner.”

22. Discuss What You’re Grateful For As A Couple

When you’ve been with each other for a while, it’s easy to take the life you’ve built together for granted. Because of this, Concepcion suggests having a conversation about what you’re grateful for as a couple. Are there specific moments that stick out? Maybe there was a challenging time that you managed to get through together. Practicing gratitude as a couple will help to solidify your bond.

23. Talk About What You’d Do If You Won The Lottery

This is a fun question to ask early on in the relationship and then again when you’ve been together for a while. “It’s important to consider that individuals grow and change as their life experiences grow and change,” Concepcion says. “As we learn more, we change our minds on things and expand. Our tastes change as do our values.” Your partner five years ago might’ve spent their lottery money on something they would never spend it on now. It’s fun to see how your partner has grown.

24. Talk About What You’ll Be Doing When You’re 60

If you want to see whether your partner sees a long-term future with you, ask about what they’ll be doing when they’re 60. Where do they see themselves living? What’s going to be their ideal day? Do they see themselves picking up any unusual hobbies? No matter how silly a question may seem, it’s still a good idea to ask. “Growing together takes effort and great conversation rooted in curiosity,” Concepcion says. “You can keep the flame burning with new discoveries.”

25. Discuss Your Views On Trust

Even if you’ve been together for a while, life experiences can change your views on big topics like trust. Consider asking your partner what it means to them today, who they trust most, and how someone would lose their trust. According to Rachel Kuhlen, relationship coach, “While couples talk about a lot, what I find is they don't explore the ‘why’ behind their thoughts and beliefs.” Having a conversation about trust can help you understand your partner on a deeper level.

26. Talk About Your Boundaries

Boundaries that might not have mattered to you or your partner last year, may be a big deal now. According to Kuhlen, “It's not uncommon for me to see couples seemingly on the same page about something ... but have very different views about their approach and what's acceptable.” Discussing your boundaries — whether it’s about family, money, intimacy, or something else — in depth is a good way to make sure you’re both giving each other what you need to feel safe in the relationship.


Dr. Josh Klapow, a clinical psychologist

Dr. Marlene Caroselli, author and speaker

Christie Tcharkhoutian, LMFT, licensed marriage and family therapist

Anjani Amladi, MD, board-certified adult psychiatrist

Dan Munro, confidence and relationship coach

Kimberly Hershenson, LMSW, licensed therapist

Stef Safran, relationship expert

Jonathan Bennett, relationship and dating expert

Risa Williams, LMFT, therapist and life coach

Leina Rodriguez, LMFT, licensed marriage and family therapist

Sarit Fassazadeh, LCSW, licensed clinical social worker

Ashley L. Annestedt, LCSW, licensed clinical social worker

Alysha Perlman, LCSW, licensed clinical social worker

Andrea Woroch, finance and budgeting expert

Stacey Greene, relationship expert and author

Lisa Concepcion, dating and relationship strategist, founder of LoveQuest Coaching

Rachel Kuhlen, relationship coach

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