13 questions to ask your boyfriend to understand his past

I’ve been with my boyfriend for 5 years now, it’s the longest relationship I’ve been in. Throughout it, the more I learn about him, the more I realize just how much our pasts shape us. 

So if you wish to understand your boyfriend better, it’s worth taking a trip down memory lane.

From childhood traumas to his happiest memories, you’ll learn about the experiences that turned him into the man he is today.

And that level of understanding is priceless. 

So, here are 13 questions to ask your boyfriend to understand his past. Let’s dive in:

1) What’s your earliest childhood memory?

I like this question because it gets the conversation going. 

Most people have pretty vague early memories, but it can be a great way to warm things up for some of the following questions on the list. 

2) How would you describe your relationship with your parents and siblings?

Now we get to the heavier stuff.

The relationship your boyfriend has with his family is crucial to how he developed growing up. 

Case in point: My boyfriend had a rocky upbringing due to the absence of his dad. 

Learning about that has helped me understand why he has certain insecurities and how they play out in his adult life. 

Not to mention – sibling relationships, oh boy. They can really shape a person. Find out how he was with his siblings and I bet you’ll get a deep insight into why he is the way he is today. 

3) Can you share a story about a tradition or a special moment from your family that has stayed with you?

Traditions mean a lot to people. 

They give them a sense of belonging and meaning. 

Finding out about your boyfriend’s family traditions or special moments is a nice way to surprise him in the future, as you create your own shared memories. 

Not only that, but it’s also a good way to find out about the values he was brought up with (and probably still holds today). 

4) What was the most significant challenge you faced during your school years, and how did you overcome it?

School can be a challenging time, but with this question, you’ll understand the issues your boyfriend faced, and the skills he developed to become resilient. 

My boyfriend was picked on by a group of guys who always wanted to steal his stuff after school (crazy, I know). 

But rather than fight them, he always found a way to avoid violence and escape. 

I see that in him now – he’s not a coward by any means. But he will seek to find a non-aggressive way of resolving an issue, and I love that about him. 

5) Who was your best friend growing up and what’s your fondest memory with them?

Our friendships have a considerable impact on us. 

With this question, you’ll learn about those whom he considers/considered closest to him. 

As he delves into his memories, you’ll also learn what his younger self was like; the things he used to do and the company he kept. 

It’ll also give you an insight into his current friendships and the types of connections he values. 

6) Have you ever faced a situation that drastically changed your perspective on life?

While this question gives you another insight into his past, it also gives you a better understanding of his values and goals now. 

Whatever he went through to change his perspective on life would have been something pretty significant and impactful. 

For example, my friend’s boyfriend lost his mom when he was a teen. It taught him to embrace every moment and live life to the fullest. 

My friend used to think he was too spontaneous and even reckless, but since speaking to him about his mom’s death in detail, she now understands where this behavior comes from, and she’s able to respect it. 

7) What was your favorite subject in school and why?

This is a more lighthearted question – we all had subjects we loved and hated, and this just opens the door for a fun conversation. 

If it does get deep, you might learn about the aspirations your boyfriend once had, and how he either fulfilled those dreams or changed them along the way. 

8) Is there any hobby or activity that you used to be passionate about but haven’t pursued in a long time?

I love this question because when your SO is feeling down, it’s the perfect time to suggest they restart an old hobby. 

When my husband was going through a tough patch, I remembered his response to this question and encouraged him to join a football club. 

He used to play a lot growing up but stopped when work got too busy. 

Rejoining a club and playing casually really helped his mental health.

So never underestimate the power of such questions. 

9) Who has been the most influential person in your life and how did they shape you?

We all grew up admiring someone. 

Whether it was a parent, grandparent, cousin, or older sibling. 

Finding out about your boyfriend’s role model will give you a peek into the qualities and personality traits he aspired to be when growing up. 

10) What was the most significant relationship you had before we met, and how did it shape your views on love and relationships?

This is a really interesting question. Approach it with an open mind, and don’t let it bring up feelings of jealousy or insecurity – your boyfriend had a life before you, just as you did before meeting him. 

But the truth is, when you learn about your boyfriend’s past relationships, you’ll understand his triggers better. 

For example, my boyfriend’s ex used to get drunk and abusive. This reminded him of how his dad acted when he was a kid. 

I then understood how triggering it was for him when I once got drunk (not abusive) and we argued. At the time I didn’t know his ex used to do this. Or his dad. It was early in the relationship. 

Since finding out though, I haven’t gotten drunk since. 

So it goes to show, you can learn a lot by sharing your relationship history, not just in understanding the past, but how it shapes your views on the future. 

11) Are there any past regrets or mistakes that you wish you could rectify?

Regrets can be a bitter thing to speak about, but they can also be great learning points. 

If your boyfriend missed certain opportunities in the past or made mistakes, talking about this could be a great way for him to learn and move on. 

And through being vulnerable with you, your relationship will also get stronger. He’ll feel he can trust you, and if you open up in return, you’ll both feel more connected with each other. 

12) What was the most challenging decision you’ve ever had to make?

When I found out that my boyfriend, at the age of just 9 years old, told his mom to divorce his dad, I knew I was with one tough cookie. 

I saw that his bravery and wisdom came from childhood. 

And you’ll find out things that’ll surprise you, too. 

Our past challenges heavily shape the people we become. Learning this about your boyfriend will probably give you a newfound sense of respect and appreciation for the man he is today. 

13) How did you handle heartbreak or disappointment in the past?

Finally, understanding how your boyfriend deals with setbacks is crucial to knowing who he is as a person and the coping mechanisms he’s developed over the years. 

Since you’re probably planning on spending the rest of your lives together, it’s good to know how your partner deals with issues. 

It’s also an insight into what might happen if you two broke up. My boyfriend has ended things pretty amicably with his exes, so I’m quite confident that if we don’t work out, it won’t turn into something nasty. 

Either way, it’s a great insight to have into your boyfriend’s behaviors.