10 Unusual Questions To Ask Your Boyfriend That Will Actually Tell You A Lot About Him

The first couple of months of a relationship is always reserved for discovering as much as we can about our new guy. We walk in with a list of questions we think will give us a good idea of who he is, finding out his all-time favorite meal, what his parents do for a living, the sitcom he’ll never get tired of watching, his older sister’s name, or where he grew up.

And while these questions do help provide us with a better understanding of him, they also fail to dig as deep as they could, leaving us with gaps in our knowledge of who he is and what his values are, and questions we’ll wish we knew the answer to – showing us that there are better, less common questions we need to be asking our boyfriend.

Here are 10 odd-but-telling questions to ask your boyfriend that go beyond his favorite color.

1. How do you envision family planning working out?

It’s crucial that we’re on the same page about family planning as our boyfriend, even if we haven’t yet been intimate. Discussing whether we’re in agreement when it comes to birth control and what kind and knowing how he’d react to a pregnancy, especially an unplanned one, tells us everything we need to know about if we should get more involved or not. If we’re considering marrying this boyfriend, then how we go about family planning includes discussing when to have children and how to navigate your sex life post-nuptials.

2. How do you react when you’re under pressure?

We might have only seen him in low-pressure situations in which he has been in control, but how does he react when he feels like the weight of the world is on his shoulders? Does he hunker down and make it work? Does he shrink away and want to disappear? His reaction to stressful situations will be telling of how he’ll react when we inevitably hit rough patches and what living with him during the stressful times would be like.

3. How comfortable are you with asking for help?

It might seem like a no-brainer to us to ask for assistance when we need it, whether that be financial aid from our parents, help with finishing a work project from a colleague, or anything else, but he might struggle to ever ask for help, even if that makes his life more difficult. By opening up this conversation with him, we’ll be able to assess whether or not this is an area we can love him better in by taking note of signals that he needs our helping hand. A reluctance to ask for help could also lead into topics that show how he views himself and others, like does he trust other people to be reliable or does he feel worthy of receiving help.

4. What do you do when you’re in the wrong?

The way we react when we’re actually in the wrong, whether with our boyfriend, our family, or at work, speaks volumes about our maturity, or lack thereof. It’s important that our boyfriend is not only able to admit he’s not always right, but that he’s mature enough to do something to make things right, whether that be apologizing or verbally stating he was wrong without having to be asked. A man who isn’t above admitting mistakes or failures is one to hold onto.

5. What do you like and dislike about how you were raised?

Even those who grew up in wonderful, loving families will have their complaints. Knowing the ins and outs of his family’s dynamics and his upbringing won’t just help us get to know him better, but it also allows us to understand him (his habits, his blindspots, his positive attributes) with better context. Along with that, discussing what he didn’t like about his family growing up will help us understand what kind of behaviors from us could trigger a bad reaction from him. It will also give insight into how and why he lives his life the way he does right now, and how he will want his future marriage and family to look and operate.

6. How much would you be willing to spend on a pet’s health?

This may seem like a particularly odd question, but isn’t it better that we know the answer when we don’t have a pet with poor health on our hands and emotions are heightened? His answer to this question will help us see if we’re on the same page when it comes to how much we value pets and how we handle tough financial decisions (especially in what would be an emotional state).

7. Do you prioritize truth, beauty, or goodness?

Of course, we value all three — but we also all process and react to them differently. Some of us always value telling the truth, no matter whose feelings get hurt; others might value harmony over bluntly stating the facts. Some people might be more willing to put extra effort into a task in order to make it beautiful; others might see that as a waste of time. Ultimately, no one will say truth, beauty, or goodness aren’t important or worth pursuing, but it’s worth asking him what he values the most, how he prioritizes them, and which of these he values the least.

8. Are you open to going to counseling (together or individually) if the need should arise?

The grand majority of adults could probably do with at least some counseling, whether or not they grew up in healthy families. We could still struggle with anxiety, loneliness, low self-esteem, anger issues, or motivation. And if our relationship comes to a point where we feel couple’s counseling is necessary, it’s important that we know his stance on going to therapy well before we find ourselves in that spot.

9. Would you be able to live without social media?

We all love social media (wait… do we?), scrolling through pretty pictures, and laughing at TikToks, but we also wouldn’t want to get involved with a guy who’s obsessed with social media and the image he has curated on it. His answer to this question will tell us if he values living real life and investing in real relationships over digital ones.

10. If you died tomorrow, what would you regret not having accomplished?

We tend to take tomorrow and our time to accomplish all of our dreams for granted. The thought of having it all taken away will bring our deepest held values and biggest dreams to the forefront – so the first one or two things he mentions when we ask him this will be very telling, offering us good insight on whether or not our values and life goals match up well.

Closing Thoughts

We all love knowing our boyfriend’s favorite color, but asking him these questions will give us answers that actually matter in the long run, answers that will help us evaluate how to better love him or help us discern how compatible we are.

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