25 Scary But Necessary Questions to Ask Your Boo to See if They’re “The One”

Determine your compatibility fast by bringing up these essential and thought-provoking prompts.

You may find yourself falling fast for a special someone. Or, maybe you are taking it slow and things are just starting to get serious. Either way, if you want to determine whether or not this person is “the one” for you, there are some questions that you have to be willing to ask them—even if they’re scary—which will help you see if you two can be compatible for the long haul.

According to Laurel House, a relationship expert at eharmony, scary questions are necessary because they illuminate the 3Cs of a relationship: Conversation, clarity and confidence. Through conversation, you can gain clarity about who your partner is and what they need. In turn, this can create more confidence for you in the relationship because you’ll know what you can give.

There are no hard and fast rules to ask the following ten questions of your boo—or vice versa. You can each answer them in the moment, or you can work off a list. Or, you can use these questions as conversation starters, letting the discussion flow and evolve naturally. The key is to lean in to the experience—not only will these thought-provoking prompts help you get to know your boo better, but they can also help you clarify who you are, what you need in a romantic relationship and how you connect best with others. Consider this a win-win!

RELATED: What It Means to Dream About Your Ex

1. What are your priorities in life?

couple women dating in bed hugging

Determine your top priorities for your partner and lifestyle and use that as your north star. Ask your partner outright what their priorities are in life: relationships, friends, family, culture, religion, money, success, home ownership, etc.

Do these align with your priorities? If so, great. If not, House says that as you go through the other questions, keep your eyes, ears, and instincts open to see if your partner’s priorities really do or don’t align with your own. If they don’t, you two may not be compatible for the long haul.

2. What is your purpose for dating right now?

Some people just want to have fun, while others are looking for something serious. It can be scary to ask if someone is looking for marriage and children early on, according to House. However, keep in mind that by asking this question, you aren’t saying “I want to marry you and have your babies right now.” All you are doing is checking that they are on the same relationship trajectory as you are.

On the other hand, if you are just looking for fun, you don’t want to waste anyone’s time if they are looking for something more serious.    

3. What is your favorite side of yourself?

When asking a partner to tell you their favorite side of themself, you’ll learn more about them as a person as well as what’s important to them in a romantic partner. If someone’s favorite part of themselves is being adventurous, they are probably looking for a bit of a daredevil who will go on spontaneous trips with them. If you are a homebody by nature, the relationship may not last long.

By paying attention to their answers, you will also find out how to make your bond stronger by determining what activities or topics will bring out their “favorite” part of themself. On the other hand, you might discover that your partner’s favorite side is one that you don’t like. It’s important to know that too, says House.

4. How do you react when you are feeling weak or scared?

couple eating dinner at home

According to House, most people will react with one of the three “Fs” when they are scared or feel weak: Fight (which looks like getting defensive and angry), freeze (which involves shutting down or getting quiet), or flee (which looks like not returning texts or calls or refusing to see you).

Too frequently, a new relationship ends because someone experiences a moment of weakness or fear and their reaction is mistaken by their partner. If you understand how your partner reacts when they are scared or overwhelmed, you will better understand that their response doesn’t mean that they aren’t interested in you. Instead, it might mean that they need a little space or some extra support.

5. What makes you angry, sad, scared or insecure? How do you want your partner to help you through those emotions?

It’s important to understand your partner’s emotional triggers and for them to understand yours. This can help stop you from accidentally triggering an emotional response. It may also help you understand why your partner may react to something in an unexpected way and give you the key to understanding how to help your partner through a tough time.

With this understanding, says House, moments of personal weakness can strengthen your connection and your relationship.

6. In your opinion, what has caused you to have that emotional trigger?

Once you understand what triggers someone, the next question is to ask why. This will help you better understand what they went through and how they became the person they are now.

7. What can you tell me about your last relationship?

couple on couch talking

It’s understandable to want to ignore your partner’s past dating history, but their dating past can be very revealing. House believes this scary question is important to ask early on in a relationship because it answers three important questions: Where were they, where are they now and where are they going?

You want to find out what attracted your partner to their ex, what their relationship was like, when they noticed there were problems, what they did to try to fix them and why the relationship eventually ended. It’s also important to ask what they did to heal and move on.

When you answer the same question, House says the key is to talk about your ex “in a confidently vulnerable way that isn’t angry, sad, or wistful. Don’t go on and on or it can feel like therapy.” House also advises telling your story in a “U strategy”: start with positivity, drop down into vulnerability, and then end with something positive.

8. What’s a non-starter for you?

Non-starters need to be talked about early—ideally, on the first date, says House. Politics is a non-starter for many people, so that’s a good place to start. Religion is another nonstarter for many. And no one can develop a meaningful relationship if there is a non-starter issue between them.

If political beliefs and preferences are important to you, you need to address them right away. If religious beliefs are a key part of your life and your future, you need to find out if your partner is on the same page right away. “You do not want to waste your time or open your heart to someone who has a belief that you can’t change or ignore,” says House.

9. How would you define our status?

It’s scary to ask for clarity when it comes to your relationship status. Is your boo still dating other people? Have they gotten off the apps? Are the two of you monogamous? Do they consider you their significant other? It’s a mistake to assume you are on the same page.

House says to imagine that you’ve been dating someone for several months, you’ve met their friends, you’re sleeping together, and you’re starting to refer to them as your exclusive partner. They, on the other hand, have no idea that you think they are committed and are still juggling multiple dates a week with other people. This isn’t necessarily because they’re a player or a bad person, says House. The reason is simply that you both never made sure you were on the same page. Clarity and communication are key in order to avoid misunderstandings about where you stand in the relationship.

10. Do you have any regrets or mistakes you’ve made?

Showing your ugly side is an essential step if you want a deep and meaningful relationship, says House. This should be “a heart-opening conversation that can immediately deepen and expand your relationship.” Asking about regrets and mistakes exposes your partner’s humanity.

Follow up by asking what made your partner realize it was a mistake, what they learned from it and how they are different or more evolved because of their missteps. It says a lot about how your partner handles conflict and hardships and how they pull themselves back up from those experiences.

Other questions to ask your boo:   

couple laughing on bridge smiling

11. What are you like when you are stressed? And how will I know that you’re feeling that way?

12. Was there a time in your life when you were physically or emotionally weak? What happened to put you in that position, and what did you do to get out of it?

13. What makes you feel most safe physically, emotionally and financially? When have and haven’t you felt that way in your past (yes, even in past relationships)?

14. What makes you feel most seen? When have and haven’t you felt that way in your past (yes, even in past relationships)?

15. What makes you feel sexy? When have and haven’t you felt that way in your past (yes, even in past relationships)?

16. What is your love language? What is an example of when you have felt loved?

17. How much personal space do you need?

18. In general, do you like to be spontaneous or are you more of a planner?

19. What would life with you look like on an average day?

20. When it comes to money, how do you prioritize retirement and savings?

21. When it comes to having fun and letting go, what does that mean to you?

22. Are there life goals that you MUST explore and accomplish?

23. How often do you like to have sex?

24. What does your ideal partnership look like?

25. What do you most love about our relationship?

Jamie Davis Smith
Jamie is a mother of four, writer and attorney. Read more