7 Challenging Questions To Ask Your Partner, Even If You’re Afraid Of The Answer

by Eva Taylor Grant
BDG Media, Inc.

While no one wants a date to feel like an interview, getting to know someone you're seeing will involve some questions and answers, even as time goes by. And to strengthen your relationship over time, it is important not to avoid asking important. Especially the ones you're afraid to know the answer to. If you're curious what tough questions to ask your significant other, this is a good place to start.

Broaching topics that seem difficult is important to keep your relationship healthy over time. "You have to be able to talk about the things that are uncomfortable because if you can't talk about these things, you won't be able to grow as a couple and have a solid foundation," Rori Sassoon, Relationship Expert and CEO of Platinum Poire, tells Bustle. And you won't know what responses you'll get until you ask.

"[...] Talking about past relationships, baggage and future plans might be uncomfortable, but it's better to be aware of where the other person stands sooner, rather than later," licensed psychologist Dr. Sal Raichbach PsyD, LCSW, of Ambrosia Treatment Center, tells Bustle. "[...] These little, but important questions will inevitably come up anyway. You can save your relationship some time and grief by asking them before they cause problems." Finding a good moment when the two of you are alone and actually talking about these things can be a good first step towards the next stage of your relationship.

Here are seven little questions to ask your partner, even if you don't want to know the answer, according to experts.


"Have You Ever Been In Love?"

Andrew Zaeh for Bustle

Whether or not someone has fallen in love before or not may be pure coincidence, but how they respond to this question can say a lot regardless.

"If your partner has never been in love but dated many people in the course of their life, it could be a sign that they can’t or won’t commit," Raichbach says. "On the flip side, if your significant other claims to have fallen in love many times, it might indicate a pattern of codependency. Falling in love takes courage, and their answers to this question will give you a sense of just what kind of courage they possess." There are many possible things to learn from this question, but it's a great way to get to know your partner better.


"What Are Your Relationship Goals?"

Andrew Zaeh for Bustle

If it's early on and you aren't quite sure whether you want to be "exclusive" yet, you can still ask questions that can help point you in the direction of where you two might be headed.

"Asking about relationship goals isn't about rushing things, it's about establishing realistic expectations," Dr. Raichbach says. "When you’re clear on your own relationship goals and you communicate your goals, you'll find out if your partner shares your vision. Most of the time there is room for compromise, but not always. Either way, you want to be able to make an informed decision." It may be scary to hear their answer if you know exactly what you want, but it's best to be with a partner who is on the same page.


"Do You Practice Safe Sex?"

Andrew Zaeh for Bustle

While this question is rooted in the practical, it can still be scary to ask. The stigma and subsequent fear around STIs is real, but that doesn't mean you should avoid the conversation about safe sex altogether.

"You have to feel like you can talk with [your partner] about having a safe sex life," Rori Sassoon says. "You should feel that no matter what, you can tell your partner anything and it is a safe space to do so. You're not going to judge them and vice-versa. It's important to have a safe space to be open." Discussing safe sex practices, as well as if and when your partner was last tested can help both of you have a healthier sex life.


"Do You Have Any Debt?"

Ashley Batz/Bustle

Debt is pretty common these days, especially among those dealing with student debt after going to college. But it's still important to talk about finances and dealing with these money situations if you're getting in deep with someone.

"While some debt may be necessary to get ahead (like college debt), a lot of debt could put a strain on your relationship, especially as it gets more serious," David Bennett, certified counselor and relationship expert, tells Bustle. "Asking this question may be hard, but I would want to know the financial situation of my partner." Finances are stressful, and opening up about this subject can be really good for your relationship.


"Is Marriage In Your Future Plans?"

Ashley Batz/Bustle

Big future goals like getting married, having kids, or living close to family can be so close to the heart that they may feel too scary to bring up, for fear that your partner won't agree with you on the issue. But if this is part of your plan, make sure it's part of their plan too.

"You might think that you are getting married after one year and they may think you are getting married in three," Sassoon says. "You need to be on the same page when it comes to your future." While overcoming dealbreakers is possible, it usually begins with an open conversation.


"Are You Friends With Your Exes?"

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Being friends with an ex is possible. But it's important to discuss how often your current partner communicates with their past ones. Even (maybe especially) if you don't want to know the answer.

"If your partner is extremely close with an ex, it could be an indicator they haven't moved on," Dr. Raichbach says. "Unresolved feelings almost always turn into problems down the road. That’s a hard pill to swallow when you’re getting to know someone, but it gives you an opportunity to address the issue before you get hurt." On the flip side, if your partner antagonizes every one of their exes, that too could be a red flag. Whatever their response, you'll learn more valuable information about your relationship.


"Are There Any Sexual Fantasies You'd Like To Explore?"

Andrew Zaeh for Bustle

Just as it's important to make sure you and your partner are on the same page about the future of your relationship, it's also valid to make sure you two are open to discussing sex And it may seem scary to ask your partner about their unspoken desires, but it could be super rewarding to talk about which fantasies you'd like to explore together.

"This is a tough [question] to ask, and you may not want to know the answer, but relationships need some spark and passion to survive," Bennett says. Knowing what your partner wants, even if they haven't brought it up on their own, is vital. Being open about pleasure and desire, even if it starts from asking a difficult question, is a good thing.

Thinking you might not want to know the answer to a question might be an indicator in itself that the question needs to be asked. But there are little ways to open up the conversation to difficult topics in ways that can be both gentle and enlightening. Whatever happens, you should feel proud asking these questions because it indicates that you're standing up for what you want in a relationship, and are prioritizing healthy communication.