15 Crazy Questions You Want to Ask Your Partner But Probably Shouldn’t

Some questions are better left unasked, especially with your partner. But where’s the fun in that? Therapist Jeff Guenther says, “Why not go for it?” From ridiculous hypotheticals to cheeky questions about their past, these outlandish questions are guaranteed to take your conversations to a whole new level of wild. Sure, you could play it safe and avoid these questions, but we all know that they will always be in the back of your mind. If you’re feeling bold, take a leap and ask! What’s the worst that could happen? Sometimes, the craziest questions lead to the best conversations!

Note: The content of this article is for informational purposes only and is not a substitute for professional advice. Always consult with a qualified professional for advice tailored to your individual circumstances.

Would You Forgive Me…?

According to Jeff, this question sounds a bit like this, “If you found out that I was hired to date you as part of an experiment where really hot people date undesirable people as a social experiment… would you forgive me?” It’s one of those ridiculous scenarios that can’t possibly be real, right? But asking your partner something like this can throw them into a spiral of confusion and doubt. Even if it’s meant to be a joke, it forces them to think about trust, manipulation, and whether they truly know your motives.

How Much Money Would It Take…?

Imagine someone offering you a ton of money to never talk to your partner again. How much would it take? Jeff asks this unhinged question: “If someone said they would pay you to go no contact with me, what’s the minimum amount you’d be willing to accept?!” This question dives straight into a territory that’s both uncomfortable and absurd. Sure, it’s meant to be hypothetical and funny, but it can make your partner think about the value of your relationship in a way that’s not only unhelpful but potentially damaging.

What If It’s Art…?

Let’s say you still have explicit, intimate photos from a previous relationship. How would your partner respond? This is one of Jeff’s unhinged questions but with a twist. Ask your partner, “What would you do if I kept explicit photos of my ex because I consider them art?!” This question isn’t just bizarre; it can stir up a whirlwind of emotions, from jealousy to confusion. Framing it as “art” may come off as an attempt to legitimize what could be seen as a betrayal, which is a surefire way to trigger insecurities.

What If I Orchestrated This Relationship…?

The way Jeff poses this unhinged question really makes you think. Ask your partner this, “If you found out I purposefully sabotaged your last relationship and inserted myself into your life so we could be together, would you say that’s romantic or a red flag?!” This question is a wild ride, blending the lines between romance and manipulation. On one hand, it’s meant to be a playful hypothetical, but it also delves into some seriously concerning territory. It forces your partner to grapple with the idea of manipulation.

What If It Makes Us Rich…?

This one is a little out there, but Jeff poses an unhinged question I’m sure a lot of people have thought about. Something crazy you can ask your partner is, “What if someone offered you money to watch me be intimate with my celebrity crush?! How much money would it take??” This question is so odd it might just get a laugh, if it doesn’t confuse them first. It blurs the lines between fantasy and reality while testing the limits of your relationship’s boundaries.

Do I Really Want To Know…?

If someone gave you the option to know every little secret about your partner, would you go for it? Big or small, light or dark, this is an unhinged question that Jeff poses that can surely test your relationship. Ask your partner, “If you had the chance to know every secret I’ve ever kept, would you take it?!” On one hand, it might seem tempting to peel back the layers and uncover every hidden truth, but what if those secrets are too heavy to bear? The transparency can become overwhelming for them.

What About The Red Flags…?

Jeff brings up a good point with this unhinged question. Ask your partner if they had the chance to find out all of your dirty laundry, and if they would take it. You might ask, “Do you want to gather all my exes in a room and ask them about my red flags?” Sure, it’s essential to know each other’s histories, but asking for a full report from your exes can feel invasive and unnecessary. Not only does it bring up your past mistakes, but it also forces your partner to evaluate their own feelings about your history.

Would It Change The Way You Feel…?

This question is definitely unhinged, but as Jeff mentions, it can be one that tests the relationship. Try asking your partner this, “If your parents died right before we met, and you found out years later that I was involved in their death, would it change the way you feel about me?!” This question hits hard and dives into some dark and twisted territory. It forces your partner to confront intense feelings of betrayal, loss, and what it truly means to love someone.

Do I Have Any Flaws…?

Your partner might see this as a trick question, but hey, they’re all trick questions. You can ask your partner something like this: “If you had the ability to get rid of any one of my flaws or imperfections, which one would it be, and why?!” This question is a playful yet pointed way to explore how well your partner knows you and how they perceive your quirks. It invites them to think critically about what they find challenging in your relationship and whether they value those imperfections.

Do You Want To Know Where This Is Going…?

This question might trip up a lot of couples. Jeff poses the intriguing question to ask your partner, “If you had the ability to know the exact day and reason this relationship ends, would you want to know?!” This unhinged inquiry dives right into the heart of commitment and uncertainty. It forces both partners to confront the inherent unpredictability of relationships, as well as their feelings about the future. While some might be curious and want to prepare for the inevitable, others may strongly oppose it.

What Kind Of Vegetable Would I Be…?

This isn’t a question from Jeff’s mind, but from my own experience. It might initially sound like a lighthearted question, but it can quickly spiral into absurd territory. Asking your partner to compare you to a vegetable can come off as silly, but it could also lead them down a path of trying to overanalyze their worth. Ask them, “If I was a Vegetable, which one would I be?!” Imagine the conversation turning serious as they ponder if you’d be a potato, tomato, or carrot!!

Are You Embarrassed…?

This last question is another that comes from my own silly thoughts. Ask your partner, “If you could pick one time that I really embarrassed you and erase it from our history, what memory would you choose?!” Imagine your partner contemplating cringe moments from years ago. They pick the time you tripped or the awkward family dinner. This is unhinged because not only do you open yourself up to past humiliations, but you also put your partner in a position to judge what they think is your biggest “flaw.”

“What do you consider cheating?”

It may surprise you that everyone has their own definition of cheating. What one person may see as cheating, others may not view in the same light. What constitutes cheating needs to be defined by each couple. You may want to ask your spouse what they would consider to be cheating so you know the boundaries of your relationship. Everyone needs to be on the same page when it comes to this one!

“Would I break your heart if…”

If you start giving hypothetical situations where you break your partner’s heart, they may get a little scared or nervous about your intentions. While knowing your relationship boundaries is important, you don’t want to threaten your partner or push them to their limits too much! The goal of any relationship should be happiness, not heartbreak. Don’t ask your partner what scenarios would cause them heartbreak unless you really want to make them doubt you.

What Do You Think About Her?

Pointing another girl or guy out to your partner is a fun and interesting way to see what type of person your spouse is attracted to. Are they still interested in people who look a lot like you, or are they more fascinated by those who are completely opposite? Next time you are out in public or scrolling the internet, point someone out and ask your spouse what they think. Just make sure you keep the conversation lighthearted and fun!

This article was inspired by the Instagram account of therapist Jeff Guenther.