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Nine Questions to Ask When Your Relationship Starts Getting Serious

Nine Questions to Ask When Your Relationship Starts Getting Serious

Is this “The ONE?”

When I was dating I remember constantly being smothered with that one giant question.

That was the point of dating, right? To magically stumble upon “The One” like finding the gold at the end of a rainbow that is being carried by a unicorn with leprechaun jockey.

But how are you supposed to know which one is the right one?

Instead of being constantly squashed by this huge question when your relationship starts getting more serious, you should ask yourself these nine questions instead:

1. Do I want to become like this person?

Marriage is like rolling Play-Doh: the more two different colors are meshed together the harder it becomes to distinguish one from another.

In marriage you begin to rub off on each other, subtly taking on traits and characteristics of the other.

Does this thought excite you or does it make you feel like you just digested a can of the aforementioned Play-Doh?

Yes, in marriage you still are your own person. And you need to have your own identity beyond your spouse. But if you don’t want to become like the person you’re dating, should you be dating?

2. Am I attracted to this person? (and more than just to how they look?)

One of the biggest lies of our culture is that attraction is solely about appearance.

If you can just get your hair, abs, complexion, and clothes just right, then “The One” will scamper to you like a squirrel to a nut factory.

However, attraction runs much deeper than looks. Sure, appearance might catch someone’s eye, but it’s personality, values, faith, heart and those other intangible things that’s going to make them stay.

Looks might deplete, but true beauty never fades.

3. Do our core values and beliefs repel or compel each other?

We all have values that direct us and help us make decisions—those beliefs that are fundamental to how you are wired, guiding your actions, thoughts, plans and purpose on this earth.

The problem is most of us have never articulated what those values really are. And if you don’t know your values, how can you expect your partner to have a clue?

These values go beyond just your stated religion. Two people who are following Christ can still have some different core values that tangibly direct their decisions.

For example, you could have a high value for responsibility and the person you’re dating could have a high value for risk. Both values are good and not necessarily incompatible, but if not articulated and discussed, it could be a point of high conflict if the responsible person likes consistency and persistence, while the risk-taker likes changing things up and going for the impossible.

Too many marriages start (and end) with vague and un-identified core values.

4. Does this person challenge me?

Is your partner trying to force you to become like them? Become like some figment of their unrealistic dating imagination? Or are they challenging you to become more like Christ and consequently, become a better, authentic you?

Your significant other shouldn’t seek to totally change you, but they should seek to challenge you to grow. And they should be growing alongside you, as well.

5. How does their family communicate?

We all go through intense, all-encompassing communication training for years; it’s called childhood. And it’s hard to un-wire 18 years of being shown how to talk and listen to others in family situations.

Sure we’re not our parents, and we can work to change our communication habits. However, for many of us, our fallback communication plan will be the one our parents laid out for us.

Holidays, especially, are giving you a glimpse into how your partner has been taught and trained. Don’t just sit back and eat that holiday ham. Sit up and take notes, because believe me, you’ll want to feel prepared for the test that comes later.

6. Do they love from their insecurities or do they love from their strengths?

I first asked this question in 11 Questions Every Twentysomething Should Ask, and I think it boils down to this: Is their love based on you or is their love based on them?

Does your partner seek out ways to understand how you receive love and meet that need? Do you do the same?

If you or the person you’re dating loves out of their insecurities, their love will be needy and selfish. After all, love can be the worst form of manipulation there is.

But when someone loves from their strengths, they know who they are and are drawing from a deep, full well to give to you without demanding a drink in return.

7. Have you both tackled your monsters?

We all have insecurities, fears, failures, painful memories, and just all around unattractive stuff we’re hiding in the back of our closet.

But just because you want to pretend your monsters don’t exist doesn’t mean they’re just going to magically go away. And marriage has the amazing ability to take all that you hoped would remain hidden and put it on stage for a nationally televised interview that your in-laws will be watching.

Tackle your monsters now. Don’t let them crush your relationship later.

As I wrote in my book 101 Secrets for your Twenties,“Newly married and living in a small apartment is no place to store a luggage set full of your baggage. Begin to ditch those bags now.”

8. Do we enjoy doing the mundane together?

Marriage is as everyday as it gets.

Marriage is budgets, laundry, broken toilets, work, weddings, funerals, births and everything in-between.

Can you envision enjoying everyday life with the person you’re dating?

Again as I wrote in my book, “If you don’t enjoy going to the grocery store with this person to buy eggs or changing the clothes at the laundromat, then you might not enjoy doing marriage. Because marriage is built on a million more mundane moments than magical.”

9. What’s their vision for the future?

How do you envision marriage after 10 years? Are you traveling the world with your spouse? Do you have three kids encased in white picket glory? Are you both working corporate jobs? Are you doing missions work in a different country? Do you have six kids and are driving a bus across the nation to perform a family rhythmic gymnastics routine at county fairs?

Your plans, goals, and ideas of the future change–but people who refuse to talk about it rarely do.

If your visions for the future look very different, it’s better to discuss it now than to be surprised by it later.

An earlier version of this article was posted at

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