Ask Him These 5 Revealing Questions

This could be the beginning of something wonderful.

You really care about him. You want to be part of his life.

But a few things he’s said bother you.

He’s got some complicated issues in his life…

And he doesn’t want you to become involved.

You have a few complicated issues in your own life…

And you’re not sure how much he wants to know about them.

Should you sit down with him and have a serious talk?

Or should you let it go and have faith it will all work out in the end?

Surely, if you love each other enough, you’ll be able to make it work no matter what… right?

No one wants to look too closely at potential problems when they’re falling for someone.

They don’t want to derail the relationship before it’s even begun.

But some couples are trying a different tactic.

They’re laying their differences out on the table from the beginning.

And I’ve got 5 questions you can use to start that conversation in a safe and playful way.

Perfection Isn’t Persuasive

When you meet someone new, you don’t want to talk about where you’re incompatible. You want to come across as his perfect match!

You’re not going to blow it by criticizing his choices or confessing your doubts.

But he knows you’re trying to impress him.

No matter how perfect you seem, he knows there’s more to the story. Everyone’s life is complicated.

So he’s skeptical. He takes everything you say with a grain of salt.

A similar thing happens in job interviews.

When an interviewer asks, “What’s your greatest weakness?” you don’t want to reveal anything too vulnerable, especially if it could be problematic for the company.

So you give the safe answer. You complain about your perfectionism or your lack of work-life balance. You tell them what you think they want to hear, never realizing they’ve heard it all before.

By playing it safe, you squander the opportunity to earn trust and stand out.

There’s a much more powerful alternative…

Lead With Your Flaws

The cost of hiring the wrong employee is high, but it’s not as high as falling in love with the wrong person.

You don’t want to get fooled by a “perfect resume,” only to find out the person isn’t what they seem.

Unfortunately, most people present their best side in the early days of a relationship. You’re led to believe they’re like this all the time. You take a chance, only to get burned when you find out the truth.

Clearly, it’s better to know about potential problems from the beginning.

But how can you start a conversation like that?

Should you steal a trick from job interviews and ask him, “What’s your greatest weakness?”

That’s not likely to go well!

If you want him to open up, set an example.

Lead with your own flaws.

Try telling him straight out, “Here’s why you shouldn’t date me.”

Then follow up by playfully asking, “Are there any reasons I shouldn’t date you?”

Here are four other ways of approaching that conversation:

  • “Let’s play a game. I’ll tell you something you might not like about me, and you tell me something I might not like about you.”
  • “What’s something your former girlfriends haven’t appreciated about you?”
  • “What problems do you think we would have if we ended up together?”
  • “In your past relationships, what have you found yourself fighting about the most? I’ll tell you what it was for me…”

These discussions work best when approached with humor and a sense of fun.

Remember, it’s not about scaring him away. It’s about inviting him into the real, unfiltered version of yourself. It’s about creating a safe space for him to be honest with you, too.

Now, some men won’t want to play the game. They prefer the illusion of perfection to the messiness of reality. That tells you all you need to know about their ability to handle complicated relationships.

If you want lasting love, you can’t dance around problems. The sooner you face them, the less frightening they’ll seem. Love doesn’t protect you from problems, but it does give you the strength to work them out.

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