20 Uncomfortable Questions You Should Ask Your Partner

You've been together for awhile now, and things are going great. You're comfortable with each other, and you know each other's quirks. But there's one topic that's still a little uncomfortable for you to bring up: sex.

You're not quite sure where to start, or what the right questions are. So you avoid them altogether and hope they'll just come up naturally. But this can be a risky move, because if they don't, you might find yourself in an uncomfortable position down the road.

The key to broaching this topic is to ask the right questions in a way that feels comfortable for both of you. That's why we've put together a list of 20 uncomfortable questions to ask your partner, so you can get the conversation started.

What Are Your Biggest Insecurities?

Do you ever feel like you're not good enough?

We all have insecurities, but we're usually hesitant to share them with others. That's why asking your partner about their biggest insecurities can be so uncomfortable. But it's a question that can help you understand them better.

When you know what someone's biggest insecurity is, you can start to build a plan to help them overcome it. And that's really the goal, isn't it? To help our loved ones become the best version of themselves?

What Are Your Thoughts on Monogamy?

Are you comfortable with monogamy? This is a question that's definitely not easy to ask, but it's important to discuss your thoughts on relationships with your partner.

Some people feel like they need to be monogamous, while others believe that having multiple relationships is the key to happiness. It's definitely a personal preference, and it's something that you should talk about before making any commitments.

This is just one example of an uncomfortable question—there are plenty more where that came from. But by hashing these things out in the beginning, you're setting the stage for a healthy, honest relationship.

What Are Your Thoughts on Having Kids?

Do you want kids? This is a question that's definitely not for the faint of heart, but it's one that needs to be asked.

Some couples are on the same page when it comes to having kids, while others have very different opinions. If you're not sure where your partner stands, it's best to ask sooner rather than later.

The important thing is to be open and honest with each other. If one person wants kids and the other doesn't, that's going to create a lot of tension in the relationship. The same goes for if one person wants more kids than the other.

If you're not comfortable asking this question face-to-face, you can always send them an email or text. But the conversation needs to happen at some point if you want your relationship to move forward.

What Is Your Relationship With Your Parents Like?

It can be tough to ask some of these questions, but they're definitely worth exploring. Questions about your partner's family can give you a lot of insight into their upbringing and the role their parents have played in their lives.

Is your partner close with their parents? Do they have a good relationship? Were they raised in a strict or liberal household? All of these things can have a major impact on your partner's worldview and how they approach relationships.

So don't be afraid to ask these uncomfortable questions. They could provide you with some valuable insights into your partner's past and what makes them tick.

Do You Have Any Unresolved Trauma?

Are you comfortable talking about uncomfortable things? Good, because I'm about to ask you some tough questions.

Questions that may make you feel a little icky inside. But they're important, so please bear with me. Do you have any unresolved trauma? Any anger or resentment that you haven't dealt with?

These are tough questions, and they're not always easy to answer. But they can help us understand our partner better and help us to build a foundation for a healthy relationship. So please, don't shy away from them. Face them head-on. It's the only way to get past them.

How Do You Deal With Stress and Anxiety?

How do you deal with stress and anxiety? Do you have any tips? Because we all know that those can be incredibly challenging emotions to manage.

It's so important to be upfront and honest about how we handle stress and anxiety. If we're not open and communicative with our partners, it can lead to a lot of misunderstandings and tension.

So, it might not be the most comfortable conversation, but it's definitely one worth having.

What Are Your Political Views?

Some questions are just too uncomfortable to ask, but they're worth asking anyway. So before you get too comfortable in your relationship, why not take a step outside of your comfort zone and ask your partner some tough questions?

Questions about political views are a great place to start. You might be surprised by the answers you get. It's important to know where your partner stands on the important issues, and this is a good way to start gaging that.

There are plenty of other uncomfortable questions out there waiting to be asked. How about religious views? Or money? What are your views on relationships and fidelity? These are all important things to know before you dive too deep into a relationship.

So don't be afraid to ask the tough questions. The answers might just surprise you.

What Is Your Opinion on Religion?

So, what do you think about religion? This is a pretty heavy question, but it's something you need to ask your partner if you want to gage how they think about the world.

Do they see religion as a force for good? Or do they think that it's responsible for a lot of the world's problems? This is a topic that can easily lead to a heated debate, so be prepared for anything.

This is just one example of an uncomfortable question that you should ask your partner. By exploring these tough topics, you'll get a better understanding of who they are and where they stand on important issues.

How Do You Feel About Money?

You may not want to ask this question right away, but it's definitely an important one to discuss with your partner. How do they feel about money? Are they savers or spenders? Do they feel like they have to compete with others when it comes to money?

These are all important things to consider, because they can have a big impact on your relationship. If one person is a saver and the other is a spender, there's going to be a lot of tension and conflict. And if one person is always competing with others when it comes to money, it can be tough for the other person to keep up.

So take the time to have this conversation and see where your partner stands. It could save you a lot of trouble down the road.

How Do You Feel About Sex?

It's time to get real. Sex is a big part of any relationship, and you need to be sure that you're on the same page. So, here are some uncomfortable questions that you should ask your partner:

How do you feel about sex? Do you enjoy it? Or is it just something that you do for me?

What are your fantasies? And do you have any reservations about sharing them with me?

What are your expectations for our sex life? Should it be vanilla, or are you open to trying new things?

What Are Your Thoughts on Commitment?

So, what do you think about commitment? It can be a pretty daunting topic, especially if your partner isn't too keen on the idea of settling down. But it's an important question to ask, nonetheless.

You need to know where your partner stands on the issue of commitment before you can move forward. If they're not ready for a serious relationship, then you need to know that now—before things get too complicated.

It might be uncomfortable to ask this question, but it's better to know the truth than to keep guessing.


You're in a relationship. You love your partner and they love you. There's nothing you wouldn't do for each other, right?

Well, maybe there are a few things.

There are some uncomfortable questions that you should ask your partner, questions that might make you squirm a little bit, but that can ultimately make your relationship stronger.

So go ahead and ask them – your partner will be glad you did.