Questions You Need to Answer about Your Date (Without Asking)

dna-without asking“For fools rush in where angels fear to tread.” – Alexander Pope (1709)

Most everyone is familiar with that quote, whether or not they know who Alexander Pope is (and, no, he wasn’t a Pope, although there was a Pope Alexander – eight of them!).

But way before the 1700s the 900s to be exact B.C.; a King named Solomon penned these words:

“Desire without knowledge is not good; how much more will hasty feet miss the way!” – Prov 19:2 (NIV)

“Desire without knowledge.”

I would be hard-pressed to come up with three words that more accurately described the typical pattern of modern romance.

And that’s why we have divorce. In other words, divorce is not inevitable in today’s culture, as we’re tempted to believe. Instead, divorce is almost always the natural result of poor relationship decisions.

Last week I shared a true story of the devastation wrought when a real person, just like you, ignored the reputation of their love interest.

This week, we talk about something even more important than reputation: character.

A person’s reputation is what others know them to be. A person’s character is who they actually are. Or as the saying goes, “‘character’ is who you are when no one’s watching.”


Though you certainly want to marry someone with a solid reputation, you won’t end up living with their reputation. You end up living with their character.

Therefore, it’s imperative that you do everything you can to dig below the surface to discern who your love interest is “when no one’s watching.”

Of course, how are you supposed to find out who someone is “when no one’s watching” if you’re watching them?

This post will give you a lot of questions to set you on the path of discovery.

  • If you aren’t currently dating, let these questions guide the way you prepare for, pray about and approach dating.
  • If you’re currently in a relationship, allow these questions to help you think critically about your date and whether your relationship should progress (or even can progress). And remember to invite trusted friends into your relationship to get their perspective.
  • Whether or not you’re currently dating, be sure to use these questions to discern your own character first. (Again, a great thing to do with good friends.)

Relational Questions:

  • How do they treat people in authority? Do they resent them or respect them?
  • How do they treat people who are serving them or work for them? Do they disparage them or treat them with dignity?
  • Do they talk about people behind their backs? In front of their backs?
  • How do they talk about their past loves? Was everything their ex’s fault?
  • How do they talk about their family; especially their parents (or the people who raised them)? Do they tend to admire, idolize or criticize them?

Emotional Questions:

  • How well do they respond to disappointment? Do they Sulk? Rage? Whine?
  • How do they respond to success? Do they brag? Get cocky? Slack off?
  • What are their fears? Do they center around money, career, family, health or zombies?
  • How do they deal with their fears? Do they tend to worry about them, repress them, or face them?
  • From where do they seem to draw their strength: from within, from the approval and support of others or from a real relationship with God? How can you tell?

Material Questions:

  • Are they responsible with money? Carry debt thoughtlessly? Spend frivolously? Give generously? Save frugally?
  • Are they responsible with time? Plan? Flexible? Waste it with hours of entertainment? Invest it in reading Date Night Advice and watching LoveEd videos?
  • Are they responsible with possessions? Obsessive? Careless? Do they Hoard? Share?
  • In all these areas do they tend to act more like stewards, owners or renters?

Identity Questions:

  • What are their aspirations? Do they center around money, career, family, travel, service, recognition, lifestyle or health?
  • What have they already done to pursue their aspirations?
  • Who do they admire in pop culture and why? What character traits do they value in those heroes: their social influence, charm, wealth, popularity, talent, superpowers, sense of humor, sacrifice, insight, generosity, discipline?
  • Then consider the same questions for who they admire in their family, their career field, politics and the Bible.

As you discover what qualities your date admires in the people they admire, you discover who your date would like to become. Then you can consider whether or not you’d like to be married to someone like that.

Of course if all the above questions were on a test all of us would flunk, but that shouldn’t mean you just throw caution to the wind, close your eyes and kiss. That’s how our culture wound up in this mess.

So, assuming Prince or Princess Charming will have some rough spots, here are probably the most important questions regarding their character:

Integrity Questions:

  • How open are they about admitting their rough spots? Are they defensive or dismissive? Or do they seem unaware they have any?
  • More importantly, how are they dealing with those character deficiencies?
  • Are they actively seeking to learn from their mistakes and break recurring patterns of failure? What’s the evidence?
  • Can they share a past struggle where they have found victory, or at least measurable and sustainable progress, or do they make promises to change and don’t?

I know that’s a lot of ground to cover, and most people don’t learn the answers to most of these questions until after marriage. Some after divorce. Some never learn. But that won’t be your story.

You’re a wise individual! You’re dating with purpose! (Click here to read the next post in this Purpose-Driven Dating series.)

This post is one in a series on Purpose-Driven Dating which we define as follows: Intentional time invested in one other person for the purpose of growing in intimacy that might lead to a life-giving, life-long marriage. Our current focus: …for the purpose of growing in intimacy… The series begins with this post.

DNA: It’s What’s For Dating

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The LoveEd study guide series, Beyond Sex & Salvation, will empower you to prepare for relational success when it counts: BEFORE YOU FALL IN LOVE! It’s NOT for couples, but for any wise individual who thinks they might want to get married sometime before they die. Check out the first two 8-lesson study guides in our store. You can walk through it on your own, but it’s more fun with friends, so consider putting together an FMU LoveEd small group study. Even better?  And ask a married couple you respect to lead it!

Categories: …for the purpose of growing in intimacy…, DATING, Friends Don't Let Friends Date Dumb, Purpose-Driven Dating