Consider how you feel and behave first
First, consider how it feels to be with your potential partner, says Kevin Gilliland, a licensed clinical psychologist and the author of Struggle Well, Live Well. These questions will help you examine your own experience and offer some clarity.
- Is it easy to be around this person? Why or why not?
- How do I behave when I’m around them?
- Are there parts of myself or my life I’m not sharing or holding back? Why?
- How do I feel about our relationship so far?
- Is there anything that feels like a red flag or gives me the “ick” feeling?
“Don’t be afraid of an ‘ick’ feeling,” says Gilliland. Instead, get curious about your reaction and explore it. It will likely come up again, so prepare to ask your partner questions about it the next time it comes up.
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What has the other person already shared with you?
Alright, now you’ve done a lot of prep work with yourself and are ready to communicate with the other person. Depending on your preference and relationship, you can plan a sit-down talk or bring up questions more casually in conversation when it feels appropriate. “Timing is so important, but it’s not a formula, it’s a feel,” says Gilliland. If the other person keeps their answers superficial, they may not be ready to have a full-on heart-to-heart,” he says.
- What information are they choosing to share and not share with me?
- What topics cause them a lot of excitement and to share many details? What topics do they avoid?
- How do they talk about relationships with friends and family?
- How do they talk about past romantic relationships?
- How do they talk about failed relationships of any kind? Do they blame others or show self-awareness about how they may have contributed and what they have learned?
Get-to-know-you questions for a potential partner
Once you are both ready, these questions will help you understand what they value about their relationships in general. You can also dive right into discussing romantic relationships, but if past dating experiences are sensitive for either of you, discussing friendships and family can lay the groundwork.
- Who are you closest to?
- What friendships matter most to you?
- What do you value in a friendship?
- What do you find challenging or get tired of in relationships?
- What do you enjoy about your relationships?
Once you have an idea about each other’s views regarding all sorts of relationships, you can dip your toe into conversations about past partners. “We have to be careful about how much detail we go into because you can’t unhear something,” says Gilliland. You don’t need to get into the nitty gritty, “what’s important is the nature of and lessons from the past relationships,” he says.
What about past dating relationships?
Gilliland says if you encounter resistance to questions about previous romantic relationships, asking what exactly about the subject makes the person uncomfortable is perfectly acceptable. “You’re learning how to communicate with one another about matters big and small. If someone doesn’t want to talk about something, that’s okay, but they should be able to tell you why and if they will be able to broach the topic in the future.”
- What went well in your past relationship?
- What did you find frustrating?
- How did you try to work through your problems?
- What did you learn from that relationship?
- Do you still have any unresolved feelings?
Partnership involves work and sacrifice, so discussing those elements is a good idea. “If you want to do whatever you want to do, don’t be in a relationship,” Gilliland says. “But if you do, what you give up pales in comparison to doing life with someone.” You can discuss those sacrifices to better understand what your partner needs to be happy. Gilliland says one of the most common problems he sees in his therapy practice is disagreement about a partner’s involvement in the partnership or marriage versus other priorities like work. But this is something you can discuss too, he says.
What about time together (versus time alone)?
Continuing to check in with your partner about alone time and time together is a good idea in any relationship phase since needs can fluctuate. When you start dating someone, it’s important to understand if they see their family every Sunday, call a best friend every day, or have a certain spiritual community that is essential to who they are.
- How do you like to balance time together?
- What kind of physical space do you need?
- How important is touch, cuddling, and sex?
- Is it easier to relax with others or when you’re alone?
- What do you enjoy doing by yourself? Do you ever go to a movie or take a trip alone?
What are your core values and beliefs?
Ask questions about faith, family, and politics, but understand that the values and beliefs behind these things matter, not necessarily the type of religion or political party. “Couples can share beliefs and values but may not necessarily vote the same way,” Gilliland says. “The important thing is to listen openly to what the person feels.”
- How often do you like to see friends and family?
- What are your thoughts about community in your city, your country, and beyond?
- What are your values and beliefs around work? How do you prioritize family, work, health, and other values?
- What mistakes do you tend to make with these priorities? (For example, working at the expense of health, etc.)
- What aren’t you willing to give up?
You won’t get through all of these questions in one conversation. It could take months of dating or even years. Sometimes, you need to discuss things multiple times to really come to an understanding, plus feelings and priorities change.
10 questions before moving in together or getting married
If you decide to take your relationship to the next level and move in together or get married, there are some specific questions that are good to consider before that step. “Ask open-ended questions. The more information you have, the better you will be at making household decisions together,” Dr. Gilliland says.
- How do you feel about this commitment? What are you excited about, and what do you worry about?
- What little things are coming up, like chores, schedules, and other life details?
- How important is it to you to design and decorate your physical space the way you want?
- How do we plan to divide things up financially?
- What are your financial priorities?
- How does the way you grew up affect your financial choices now?
- How important is it to entertain and have guests?
- How do you feel about pets?
- What are your feelings about having children?
- What does happy cohabitation or marriage look like?
If only going through this list ensured a happy-ever-after relationship! But these 40 questions are just to get you started.
“You don’t want to make the mistake of thinking, ‘I asked all the questions, so now we’re good,’ because you’ll never be able to ask all the questions,” Gilliland says. “There are all sorts of card games and books of questions you can try too; I’m a big fan of those,” he adds. The important thing is developing the ability to communicate and talk about difficult things. That skill will help you through anything you encounter as a couple in the future.
