In the early stages of dating someone, it can feel like you’ll never run out of questions to ask. Once you’re in a long-term relationship, however, it’s easy to get complacent — you may assume you pretty much know all there is to know.
The truth is, there’s always more to discover in any relationship, and whether you’ve been dating your current partner for 10 months or 10 years, experts say asking certain questions can build intimacy, spark meaningful discussions, and maybe even uncover some surprising tidbits.
“In the beginning of a relationship, curiosity tends to be effortless,” says Kiara Luna, LMHC, CEO and founder of Knew You Psychotherapy. “You want to know everything about your partner. But over time, as familiarity sets in, that curiosity fades. Partners stop asking, and without realizing it, they stop discovering.”
RELATED: The Best Ways to Improve Your Relationship
But according to Luna, questions are bridges that connect us to the parts of our partners that might otherwise go unnoticed — like unspoken needs, evolving dreams, and hidden fears.
Scott Valdez, cofounder and CEO of Ari and founder of VIDA Select, insists that if there’s one thing he learned from a decade of matchmaking it’s this: couples who stay together aren’t necessarily the most compatible on paper — they’re the ones who never stop being curious.
“When couples come to me saying they’ve ‘grown apart,’ I usually find they stopped learning about each other somewhere around year two,” he adds. “They’ve been operating on assumptions and outdated information ever since. The strongest relationships I see are the ones where both people treat questions like essential maintenance.”
1. “What’s something you’ve always wanted to try but haven’t had a chance to yet?”
“This question opens the door to adventure, spontaneity, and possibility,” says Luna. “It’s easy to assume you know all of your partner’s dreams, but people evolve. Maybe they’ve always wanted to learn salsa dancing, or travel to a specific country. And their answer to this question might even surprise you. More importantly, it gives you an opportunity to support and encourage them in a new way.”
Luna notes that this is a great question to ask a few months into dating, but it’s also useful in long-term relationships when life starts feeling predictable. Asking can reignite a sense of novelty and excitement, while giving you inspiration for your next date night or shared bucket list.
2. “What is your definition of love?”
“I like broad open-ended questions that just get someone talking,” says Dr. Wendy Walsh, relationship expert at DatingAdvice.com. “And this is one of my favorites.”
As Walsh explains, everybody has an internal working model for love, an idea of what love should be — but many people wrongly assume that their definition is the same as their partner’s. By asking this question, you unlock the opportunity to identify those discrepancies while also finding common ground in what love looks like to you.
RELATED: What Does True Love Feel Like?
3. “What does our relationship look like to you in 2 years, 5 years, and 10 years?”
Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, says this is a great question to bring up about six to nine months in, once you and your partner have established a serious relationship — or even a few years in when things are feeling a bit stagnant.
According to Trombetti, this question can give you an idea of whether your and your partner’s goals are aligned, and also to figure out how to merge your hopes and dreams while making any necessary compromises.
4. “When you’re upset, how should I approach you?”
When some people are upset, they like to have some space to process their emotions. Others may want a sounding board to talk through their issue, or some soothing physical touch.
And unless you ask your partner about their preferences, you may not be able to give them what they need in that moment. That’s why Dr. Betsy Chung, a clinical psychologist and relationship expert at RAW dating app, recommends asking this.
“This question can help two individuals get past stressful conflict with more direction, which can greatly reduce the building of resentment,” she explains.
“Without knowing what your partner wants when they’re upset, well-intentioned efforts can create more distance instead of closeness,” adds Luna. “You may learn that maybe your partner needs a hug instead of advice. Maybe they need to vent without solutions. Maybe they need silence before talking. By asking this question, you’re learning how to be their safe space, on their terms.”
RELATED: How to Use ‘Solve Languages’ to Improve Your Relationship
According to Luna, this is a crucial question to ask before moving in together — as well as when life throws your partner a huge obstacle, such as losing a loved one or a job.
5. “What do I do that helps you to feel safe with me? (And what could I do better to make you feel safe?)”
“Security needs are incredibly personal,” says Valdez. “I had this client whose girlfriend needed him to text when he was out with friends — not because she was controlling, but because her ex would disappear for days without warning and it gave her anxiety.”
“Another client discovered his girlfriend felt most secure when he remembered details about her work conflicts,” he adds. “This question gets to those specifics. You basically get your partner’s security code — those specific actions that either build trust or accidentally damage it.”
RELATED: Habits That Erode Trust in Relationships
Your partner’s response may range from how you handle confrontation with them or how directly you talk about the future, to how you handle communication during busy periods.
“Try this around four to five months into the relationship, once you’ve established some patterns, and then revisit before any major life change,” says Valdez. “If they have trouble answering, I sometimes tell clients to offer an example: ‘For me, I feel secure when you call instead of text if you’re running late.’ This gives them a model without putting words in their mouth.”
RELATED: How to Build Intimacy in a Relationship
6. “What’s one thing you’d like us to do differently in our relationship?”
Sometimes it’s hard to find the right time to share what you’d like to change about your relationship.
By asking this question, you’re taking the burden off your partner to bring it up — and offering them an opportunity to share, says Dr. Michael Kane, a psychiatrist and chief medical officer at Indiana Center for Recovery.
And the beauty of this one is that you can ask it at any point in your relationship — and ideally, continue asking it at least on an annual basis.
Valdez says it can also be helpful to ask what your partner would like to do differently during a disagreement — say, after your first sight, or after a particularly heated talk.
“Some people need you to lower your voice during tense moments,” he explains. “Some need you to stop proposing solutions and just listen. Some need 20 minutes of cool-down time. Some need reassurance that you’re not questioning the whole relationship just because you disagree about something.”
RELATED: How to Handle a Relationship Argument
“Consider following up with, ‘Is there anything I do during disagreements that makes things harder for you?’” Valdez suggests. “This identifies those unexpected triggers that you might not realize are escalating things.”
7. “What’s your top current stressor, and how can I best help you cope?”
“This question builds empathy and a sense of teamwork as well as sharing burdens,” says Kane.
Kane advises asking this question during big life transitions, or whenever your partner has a lot on their plate.
8. “What were your early experiences with money, and what would you like to do the same/different?”
According to Rabbi Shlomo Slatkin, a licensed clinical professional counselor, certified Imago Relationship Therapist, and cofounder of The Marriage Restoration Project, understanding how your money was dealt with while they were growing up can give you some valuable insight into their current financial habits.
“Money can be a charged topic for most couples and it almost always comes from childhood experiences,” he explains.
If money was a source of stress during their early years, or their parents spent money frivolously without ever saving for the future, that probably affected how they view and manage money now.
RELATED: How to Tell If You’re Financially Compatible With Your Partner
Getting this kind of background information can help you to build empathy for how they handle money, which will likely impact your relationship in the long term — particularly if you pay bills together, own a home together, or plan to have children.
9. “What are your goals this week, and how can I support you in achieving them?”
Walsh says this is a great question to ask at any point in a long-term relationship, but particularly when your partner seems overwhelmed.
“You’re going to learn more specifics about their goals and values as well as your potential role in helping them meet those,” she explains.
Remember: The key part of this question is the second part. Don’t assume that you know how to help your partner reach their goals. They may only want emotional support, or they may ask for more concrete acts of service, like running an errand for them. Either way, asking shows that you want to show up in the way that’s most helpful for them.
RELATED: Signs You’re in a Healthy Relationship
10. “If you could change one thing about our life, what would it be?”
According to Walsh, this seemingly simple question can be surprisingly illuminating.
“Sometimes partners haven’t even stopped to consider what change would help them feel happier in their relationship,” she explains. “They just have a nagging feeling of malaise that they haven’t identified nor articulated. And plenty of times, the things they want to change are an easy fix.”
This question gives you the chance to shed light on how to increase your partner’s satisfaction — which, in turn, will benefit your relationship, too.
You Might Also Dig:
How to Help a Partner Through a Difficult TimeRelationship Lessons All Men Should Learn Before 40Couples Exercises to Build Intimacy & Improve Communication
The truth is, there’s always more to discover in any relationship, and whether you’ve been dating your current partner for 10 months or 10 years, experts say asking certain questions can build intimacy, spark meaningful discussions, and maybe even uncover some surprising tidbits.
“In the beginning of a relationship, curiosity tends to be effortless,” says Kiara Luna, LMHC, CEO and founder of Knew You Psychotherapy. “You want to know everything about your partner. But over time, as familiarity sets in, that curiosity fades. Partners stop asking, and without realizing it, they stop discovering.”
RELATED: The Best Ways to Improve Your Relationship
But according to Luna, questions are bridges that connect us to the parts of our partners that might otherwise go unnoticed — like unspoken needs, evolving dreams, and hidden fears.
Scott Valdez, cofounder and CEO of Ari and founder of VIDA Select, insists that if there’s one thing he learned from a decade of matchmaking it’s this: couples who stay together aren’t necessarily the most compatible on paper — they’re the ones who never stop being curious.
“When couples come to me saying they’ve ‘grown apart,’ I usually find they stopped learning about each other somewhere around year two,” he adds. “They’ve been operating on assumptions and outdated information ever since. The strongest relationships I see are the ones where both people treat questions like essential maintenance.”
1. “What’s something you’ve always wanted to try but haven’t had a chance to yet?”
“This question opens the door to adventure, spontaneity, and possibility,” says Luna. “It’s easy to assume you know all of your partner’s dreams, but people evolve. Maybe they’ve always wanted to learn salsa dancing, or travel to a specific country. And their answer to this question might even surprise you. More importantly, it gives you an opportunity to support and encourage them in a new way.”
Luna notes that this is a great question to ask a few months into dating, but it’s also useful in long-term relationships when life starts feeling predictable. Asking can reignite a sense of novelty and excitement, while giving you inspiration for your next date night or shared bucket list.
2. “What is your definition of love?”
“I like broad open-ended questions that just get someone talking,” says Dr. Wendy Walsh, relationship expert at DatingAdvice.com. “And this is one of my favorites.”
As Walsh explains, everybody has an internal working model for love, an idea of what love should be — but many people wrongly assume that their definition is the same as their partner’s. By asking this question, you unlock the opportunity to identify those discrepancies while also finding common ground in what love looks like to you.
RELATED: What Does True Love Feel Like?
3. “What does our relationship look like to you in 2 years, 5 years, and 10 years?”
Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, says this is a great question to bring up about six to nine months in, once you and your partner have established a serious relationship — or even a few years in when things are feeling a bit stagnant.
According to Trombetti, this question can give you an idea of whether your and your partner’s goals are aligned, and also to figure out how to merge your hopes and dreams while making any necessary compromises.
4. “When you’re upset, how should I approach you?”
When some people are upset, they like to have some space to process their emotions. Others may want a sounding board to talk through their issue, or some soothing physical touch.
And unless you ask your partner about their preferences, you may not be able to give them what they need in that moment. That’s why Dr. Betsy Chung, a clinical psychologist and relationship expert at RAW dating app, recommends asking this.
“This question can help two individuals get past stressful conflict with more direction, which can greatly reduce the building of resentment,” she explains.
“Without knowing what your partner wants when they’re upset, well-intentioned efforts can create more distance instead of closeness,” adds Luna. “You may learn that maybe your partner needs a hug instead of advice. Maybe they need to vent without solutions. Maybe they need silence before talking. By asking this question, you’re learning how to be their safe space, on their terms.”
RELATED: How to Use ‘Solve Languages’ to Improve Your Relationship
According to Luna, this is a crucial question to ask before moving in together — as well as when life throws your partner a huge obstacle, such as losing a loved one or a job.
5. “What do I do that helps you to feel safe with me? (And what could I do better to make you feel safe?)”
“Security needs are incredibly personal,” says Valdez. “I had this client whose girlfriend needed him to text when he was out with friends — not because she was controlling, but because her ex would disappear for days without warning and it gave her anxiety.”
“Another client discovered his girlfriend felt most secure when he remembered details about her work conflicts,” he adds. “This question gets to those specifics. You basically get your partner’s security code — those specific actions that either build trust or accidentally damage it.”
RELATED: Habits That Erode Trust in Relationships
Your partner’s response may range from how you handle confrontation with them or how directly you talk about the future, to how you handle communication during busy periods.
“Try this around four to five months into the relationship, once you’ve established some patterns, and then revisit before any major life change,” says Valdez. “If they have trouble answering, I sometimes tell clients to offer an example: ‘For me, I feel secure when you call instead of text if you’re running late.’ This gives them a model without putting words in their mouth.”
RELATED: How to Build Intimacy in a Relationship
6. “What’s one thing you’d like us to do differently in our relationship?”
Sometimes it’s hard to find the right time to share what you’d like to change about your relationship.
By asking this question, you’re taking the burden off your partner to bring it up — and offering them an opportunity to share, says Dr. Michael Kane, a psychiatrist and chief medical officer at Indiana Center for Recovery.
And the beauty of this one is that you can ask it at any point in your relationship — and ideally, continue asking it at least on an annual basis.
Valdez says it can also be helpful to ask what your partner would like to do differently during a disagreement — say, after your first sight, or after a particularly heated talk.
“Some people need you to lower your voice during tense moments,” he explains. “Some need you to stop proposing solutions and just listen. Some need 20 minutes of cool-down time. Some need reassurance that you’re not questioning the whole relationship just because you disagree about something.”
RELATED: How to Handle a Relationship Argument
“Consider following up with, ‘Is there anything I do during disagreements that makes things harder for you?’” Valdez suggests. “This identifies those unexpected triggers that you might not realize are escalating things.”
7. “What’s your top current stressor, and how can I best help you cope?”
“This question builds empathy and a sense of teamwork as well as sharing burdens,” says Kane.
Kane advises asking this question during big life transitions, or whenever your partner has a lot on their plate.
8. “What were your early experiences with money, and what would you like to do the same/different?”
According to Rabbi Shlomo Slatkin, a licensed clinical professional counselor, certified Imago Relationship Therapist, and cofounder of The Marriage Restoration Project, understanding how your money was dealt with while they were growing up can give you some valuable insight into their current financial habits.
“Money can be a charged topic for most couples and it almost always comes from childhood experiences,” he explains.
If money was a source of stress during their early years, or their parents spent money frivolously without ever saving for the future, that probably affected how they view and manage money now.
RELATED: How to Tell If You’re Financially Compatible With Your Partner
Getting this kind of background information can help you to build empathy for how they handle money, which will likely impact your relationship in the long term — particularly if you pay bills together, own a home together, or plan to have children.
9. “What are your goals this week, and how can I support you in achieving them?”
Walsh says this is a great question to ask at any point in a long-term relationship, but particularly when your partner seems overwhelmed.
“You’re going to learn more specifics about their goals and values as well as your potential role in helping them meet those,” she explains.
Remember: The key part of this question is the second part. Don’t assume that you know how to help your partner reach their goals. They may only want emotional support, or they may ask for more concrete acts of service, like running an errand for them. Either way, asking shows that you want to show up in the way that’s most helpful for them.
RELATED: Signs You’re in a Healthy Relationship
10. “If you could change one thing about our life, what would it be?”
According to Walsh, this seemingly simple question can be surprisingly illuminating.
“Sometimes partners haven’t even stopped to consider what change would help them feel happier in their relationship,” she explains. “They just have a nagging feeling of malaise that they haven’t identified nor articulated. And plenty of times, the things they want to change are an easy fix.”
This question gives you the chance to shed light on how to increase your partner’s satisfaction — which, in turn, will benefit your relationship, too.
You Might Also Dig:
How to Help a Partner Through a Difficult TimeRelationship Lessons All Men Should Learn Before 40Couples Exercises to Build Intimacy & Improve Communication