Updated on Apr. 25, 2023
Starting or maintaining a healthy romantic relationship can be fun, but also requires some wise intention. Here are therapist-approved date night questions, whether it's your first date or your 50th. Plus, what one psychologist says your ultimate relationship goal should be.
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Looking to build or strengthen your relationship? Chances are you’ve already been told to try regular date nights. It’s a good tip, but know this: Not all date nights are created equally when it comes to a healthy relationship, according to a 2021 sociology study.
The researchers found that couples who just did something leisurely together—like going out to dinner—saw a small boost to their relationship…but couples who planned a specific kind of date saw their relationship strength and happiness skyrocket.
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The difference between a good date and a great date can be summed up in one word: Communication.
“How couples communicate wants, needs and desires and how they receive that information is the foundation of the relationship,” says Vijayeta Sinh, PhD, supervising psychologist at the Icahn School of Medicine at Mount Sinai and founder of Therapy Couch in New York City. “In happy relationships, communication isn’t just one thing, it’s everything.” It’s one of the six characteristics of a healthy relationship.
According to the 2021 study, there are two types of relationship communication styles during date nights:
To be clear, both groups experienced an increase in relationship satisfaction. But the group who communicated openly and who intentionally based their dates on speaking positively and doing exciting, engaging things together experienced a higher, longer-lasting improvement.
(Here are some relationship communication quotes that will inspire you to speak up and listen to your partner.)
When you’re first dating, it feels natural to ask lots of questions as a way of getting to know the other person. These questions foster a sense of closeness and understanding, leading to better connection, says Dr. Sinh.
But date night questions aren’t just for getting to know new people. They can also help long-term partners reconnect and improve relationship communication.
Asking and answering date night questions is a way to comfortably open up topics of your lives. This allows you to talk, share, and get know each other better without worrying that topics are too personal or you’re being too intrusive. “It sets parameters for what is OK to discuss,” says Jane Greer, PhD, a New York-based marriage and family therapist and author of the relationship self-help book What About Me?
But it isn’t just the topic of the questions and the substance of the answers that matters. The acts of asking and showing interest, listening, and building intimacy make a date night Q&A such an important relationship tool, Dr. Sinh says.
Ready to open the lines of communication between you and a potential partner? Get ready to ask (and answer) questions that’ll bring you closer together.
These therapist-approved questions (that are in no particular order) will help you gather information about someone new and learn more about your compatibility with each other. (Keep reading for questions that work better for long-term partners.)
The five love languages offer a bit of pop psychology from licensed therapist Gary Chapman. The five love languages focuses on the fact that people give and receive love in different ways. These include physical touch, words of affirmation, acts of service, quality time, and gifts.
“Too many people assume that their partner expresses love in the same way they do and that’s usually not the case,” says Dr Sinh. Asking your date how they communicate love gives you important intel moving forward in the relationship, she says.
According to Joe Kort, PhD, a relationship therapist and founder of The Center for Relationship and Sexual Health in Royal Oak, Michigan, this can tell you a lot about the person and how they act in a relationship.
Note: You should also be willing to be open and honest about your dating history in return. You don’t have to get into all the gritty details about the past—especially if it’s still in the very early stages of the relationship—but this is an important topic to address, says Kort. (Here’s what a narcissist does at the end of a relationship.)
According to Kort, this can tell you a lot about the person and how they act in a relationship. (Here’s what a narcissist does at the end of a relationship.)
Greer recommends asking this question because it gives you an idea of your partner’s dating history and can tell you how ready and available they are to start a new serious relationship. (This is how to deal with dating rejection.)
Asking this question can help you get a sense of how they learned to be in a relationship.
“It isn’t always the most accurate, as there could be mental health problems in their family members, but hearing how things were in their childhood and their current relationship with parents and siblings can tell you quite a bit,” Kort says. (Keep an eye out for these relationship red flags.)
This question is a good follow-up. According to Greer, it’s a way to gain information—in a nonthreatening or non-probing way—as to their family dynamics.
You may learn how well they get along with family members, if there are existing conflicts that might impact your relationship, as well as who may approve or disapprove of your relationship going forward.
Plus, open-ended date night questions leave room for the conversation to flow naturally.
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This question tells you about their professional dreams and ambitions. It also reveals whether their career is something they planned from a young age or if the opportunity came along through a friend or family member.
“It shows how they connect in the world, as well as how ambitious they may be,” Greer says.
Questions like this are valuable ways to gather information and learn about a potential partner. Greer says it opens up the topic of the hobbies they may have.
Consider what it might say about someone if they plan to book a sports vacation versus a sightseeing tour of a city or a relaxing week at the beach. It gives you an idea of what you have in common and may enjoy doing together. (Here are the signs you’re dating a narcissist.)
Clear boundaries and expectations make for better sex so even if you don’t feel comfortable having this conversation on a first date, it is something that must be addressed before you have sex, says Dr. Sinh.
This should be an ongoing conversation, both in and out of the bedroom, to make sure both of you are having your needs met.
Once you’ve been dating longer than a year, it’s key to keep asking questions and getting to know your partner. Being curious is important, says Kort.
“People often get upset when they learn something new [about a long-term partner after] many years, as if they should know everything,” he says. “That is impossible.”
Greer says that asking questions conveys a continuing genuine interest in knowing who your partner is. It also shows you care about them and want to support them in their lives. Plus, she says, it helps establish trust, safety, and intimacy in your bond. (Similar to these questions that help people fall in love.)
Here are some date night questions for established couples that will help spark conversation.
Relationships are built on both partners being willing to sacrifice and serve the other. Asking this question shows that you care about your partner’s needs and want to help make their life a little easier, says Dr. Sinh.
“The ultimate relationship goal should be building togetherness, to stay unified even when you encounter fights, difficulties, miscommunications,” says Dr. Sinh.
But this goal is based on many smaller goals, and it’s good to check in with your partner about areas that they’d like to improve and how. For instance, one goal may be to do more date nights!
Questions that involve a measure of unpredictability, even risk, allow partners to show a lighter, funnier side, and pull us out of day-to-day stress.
“Play comes before foreplay,” says Stephanie Newman, PhD, a clinical psychologist in New York City. “Go light. Have fun. Flirt. Ask something silly, even ridiculous.”
This is one example of a silly, potential tension-busting interaction that could help stressed-out significant others dial down tension, transition to a more light-hearted evening, and build intimacy.
Asking about work shows interest in how their job is going and enables them to share some of the happenings, be it frustration with a colleague or a project that’s going well. “It establishes trust that you are interested in them and what they are doing,” Greer says.
Sure, it’s an old standby, but that’s for good reason. It’s a simple but effective way to connect. (Here are ways to make your partner feel loved.)
Date night questions aren’t all about learning new information. In times of conflict, or when the bond feels shaky, communication provides a route to a potential fix, according to Newman.
Asking this question about past trips that you have been on as a couple helps relive shared moments and allows couples to escape from any current tensions.
“They can serve as reminders of the good times, and of why you got together in the first place,” Newman says.
Another great question is to ask how a family member is doing. If your partner is concerned about a particular family member, follow up.
“This makes room for being open, honest, and perhaps vulnerable if there is a sticky situation or problem that they are dealing with,” Greer says. “And it lets them know it is safe to tell you about it.”
Again, couples often don’t talk openly about their sex and erotic lives—even after being together for an extended period.
“I always tell couples: Don’t assume that you both agree about what [monogamous] means,” he says. “Talk about it openly and honestly. Make sure you are on the same page and, if you’re not, this is your chance to be.” (Here’s how to improve your sex life.)
Yes, even couples who are together for over 20 and 30 years still learn from and about each other. “I believe it can be fun to sit with curiosity and not believe you know everything about your partner,” Kort says. “Ask and tell.” This is one of the best date night questions to ask.
Although this isn’t a question, it’s how Kort starts every couple’s appointment. He recommends couples do it on date night, too.
“An appreciation is anything you see in your partner’s behavior, personality traits, or anything that you want them to know you appreciate,” he says. “A brag is a stretch you have done for them that was out of your way or comfort zone.”
The reason to say this to each other is simple: These things are often invisible, unsaid, and taken for granted. It is a great way to bring them into the open.
Knowing that these are therapist-approved date night questions will hopefully give you and your partner the confidence and security to make open-ended, exploratory inquiries. At the same time, asking these questions will make your partner feel important. The activity makes clear that who they are and what makes them tick is not only of interest to you but also really matters, Greer says.
Newman agrees, adding that questions can open doors in relationships. “Date night is the perfect opportunity to show your curiosity and interest in your significant other,” she says. “It isn’t only about the content, of course. The moments spent talking and listening are what matters in a relationship.”
The art of asking and answering can build rapport and strengthen your connection with your partner. Questions that foster communication, empathy, and play are key to healthy partnerships. They help solidify relationships.
Additional writing and reporting by Charlotte Hilton Andersen.
Medically reviewed by 
