6 Serious Questions To Ask Your Boyfriend

So you’ve been together a while. You’re having thoughts that maybe he’s ‘the one’. But what are the chances that this is the right guy to head into ‘serious’ territory with? It’s time to ask some searching questions – and the answers you receive will help you decide if he’s honestly the man to consider spending the rest of your life with…

1. Why did his last relationship fail?

Couple Sitting

Of course, when you ask your guy this you’re only going to receive one side of the story – his. But it will give you some insight into his psyche. Perhaps he wasn’t ready for a serious relationship. Or maybe she (or he) cheated. Maybe he really is Mr. Nice Guy and was used and abused by his last partner. There are a million and one reasons why a relationship comes to an end.

But hey, while it’s natural to want to know every last thing about your guy, sometimes it’s not actually necessary to dig too deep. Let him tell you as much as he feels comfortable – pushing to find out more isn’t proactive for either of you. After all, you’re only getting his view on why it didn’t work out. It’s human nature to put the blame onto the other person, and in all reality, relationships fail due to reasons that both are responsible for.

Unless it’s down to something fundamental (violence, for example), the reason his last relationship ended is not going to be a reason that yours might end in the future.

2. How does he deal with disagreements?

What this is really about is learning his style of communication. Each of us tends to fall into one of five different categories.

These are:

  • Assertive
  • Aggressive
  • Passive aggressive
  • Submissive
  • Manipulative

While this might sound a bit scientific, understanding what his is (and, when it comes to it, yours) can help both of you understand how to deal with any arguments that might occur in the future.

Of course, at the beginning of a relationship disagreements tend not to surface. It’s only when you pass the honeymoon stage that you might butt heads over certain issues. Arguments aren’t necessarily a bad thing. But knowing how each other handles them will provide valuable insight for each of you to understand how the other reacts.

 3. Cheating. OK, or not OK?

Couple Conversation

You might think you know the answer to this. But in reality, your guy might not view infidelity to be such a big deal. It’s vital to find out his views on whether you’re now an exclusive ‘item’, or if he considers that playing the field might still be considered ok.

There are more subtle ways that cheating can hurt a relationship. For example, is he friends with loads of girls on Facebook? Does he send and receive texts from other girls? Has he got close female friends he confides in more than you? While these might not actually be a problem, such scenarios could cause you undue hurt if you find out about them further down the line…

Discussing what the boundaries are in your unique relationship sooner rather than later can really help prevent untold heartache in the future.

4. Pillow talk – what about kids?

Family Sunset Dock Ocean

It might seem a little soon to be talking about starting a family. But if you’re dream is to have a home with a bunch of kids running around and his isn’t, better to find out now. The thing is, having the conversation about having kids at the beginning of a relationship means that you both start on the same page. If you want them and he’s adamant he doesn’t, then you might want to question whether investing time and emotion into this relationship is actually worth your while.

 5. Work stuff: How would you work it if one of you got a job in another city, state, or even country?

Man Working Laptop Big City

This is quite a biggie, because in today’s work climate, it’s quite likely that one of you will be offered a job elsewhere at some point in the future. You need to know his feelings on this, because they might differ considerably to yours. How would he feel about having to move if you got the job offer? Or could he see a long distance relationship working? It might be that one (or both) of you are going off to college or uni.

The chances of a long distance relationship lasting are, no matter what the myth surrounding them, no better or worse than any other type of relationship. But it’s not about that – it’s understanding what his view would be should the situation might actually come up.

6. Cut to the chase – how much is he worth?

Hey girls, we’d all like to marry a millionaire. But having this conversation isn’t about being a gold digger. It’s actually a valid one to ask, because his finances (and, for that matter, yours) will have an impact on your future together.

For instance, does he have any debts? If so, what are they for and how large are they? What about his credit score? If it’s bad, this could impact on future decisions, such as being able to get the funding to purchase your own home.

Ask him about how he manages his money. Because when you’re living together the financial burden is going to be a joint one. Knowing at an early stage who might have failings in this issue is key to finding a working solution that’s best for both of you.

And most importantly…

If you’re at the stage to ask these probing questions, you’re going to need to be prepared to reciprocate. The chances of your relationship moving forward and getting stronger is all about communication. The better it is, the better the relationship will be.