9 Tricky Questions To Ask Your Boyfriend To Make Him Fall Even More In Love With You

These deeper questions will help you find out more about what kind of person he is.

9 Tricky Questions To Ask Your Boyfriend Getty

By Brittany Christopoulos

I’m a firm believer in using verbal communication to make relationships work.

The moment you stop talking is the moment when problems start.

To enhance some deeper conversation, it’s important to ask creative, if sometimes tricky, questions that will really prompt your partner to think.

Their answers will help you see if you share the same views, help learn about their past and bring any crucial deal-breakers that you haven’t yet had the opportunity to discuss.


Here are 9 tricky questions to ask your boyfriend to deepen your connection and fall more deeply in love:

1. Which year of your life would you relive and why?

When they give this answer, they are more than just highlighting a fun or memorable experience that occurred in the year they choose.

This question will bring them back to a time of happiness or love and will help explain why they are the way they are.

RELATED: 50 Questions To Ask Your Boyfriend Or Girlfriend (Before Your Relationship Gets Too Serious)

2. Does spending time with people exhaust you or do you love it?

This is an important question to ask, no matter your personality. Whether you’re an introvert, an extrovert or somewhere in-between, this could be a huge deal-breaker, as it could also be for your partner.


If they love being around other people 24/7, and you don’t, these personality differences could create conflicts.

3. What is something you consider unforgivable?

Answers to this question can vary from past experiences to just a general opinion.

But it’s important to know your partner’s morals and what not to do to them to hopefully prevent a much larger conflict, which could easily arise if you unintentionally do something they couldn’t forgive you for.

4. Do you believe things are meant to happen or that they just do?

This question gives you a glimpse of the kind of drive and beliefs your partner has.

If they just let things happen, they’re laidback and probably haven’t thought much about this.


5. Which qualities do you think a healthy relationship should have?

Perfect! An easy question to see your partner’s values, morals, expectations and opinions on issues that can literally make or break your relationship.

Plus, it’s nice to discover more potential similarities.

RELATED: 9 Tried-And-True Signs You're In A Genuinely Healthy Relationship


6. What’s something you’re glad you never have to do again?

It’s so important to learn about regrets your partner may have because it could explain a large part of why they are the way they are today.

Or, it could bring up a hilarious story from the past and totally make you laugh. This question could go one of two ways!

7. What is something your other relationships lacked that was a problem for you?

If your partner can answer this almost instantly, then they’ve had time to reflect on their past relationships.

This question is also a huge indicator that they know what they want in someone and they have an idea of the ideal qualities they need to have a successful relationship.


8. What kinds of tasks do you procrastinate most on?

Again, another important question because it can teach you some of their biggest flaws.

If you are a go-getter, but they are more lazy about things that are meaningful to you, could this be something that could harm your relationship? It’s so crucial to know.


9. What’s the best way to end a long day?

This can be more of a fun question and a good way to end your discussion period, simply because you are finding out how they like to relax in their downtime or how they act after a busy day.

Stress affects everyone differently and knowing how they like to end their day benefits you because you’ll know what to do in the future.

Having big discussions with your partner doesn’t need to be as scary as it seems.

Sure, it’s daunting, but there are ways of getting these crucial answers without having to be so serious.

It’s about sounding lighthearted and interested in getting to know them on a deeper level than the surface-level questions that make you feel comfortable.


RELATED: 20 Thought-Provoking Questions To Ask Your Guy Instead Of 'How Was Your Day?

Brittany Christopoulos went to Seneca College for broadcast journalism, where she mastered the art of television and radio announcing.