The Unsexy Question You Need To Ask By The Third Date

Everyone wants to pace the tough questions for fear of turning off the person you’re dating. 

Problem is, if you wait till you catch feelings, you’re less inclined to ask and more inclined to minimize or spin an answer that would be a deal breaker if you learned of it early on. 

Which is why I want you to ask my favorite unsexy question by the third date:

“Why’d you and your ex break up?”

I know. I cringe a little too when I think about it. 

But the answer is one of the best litmus tests for assessing compatibility. 

Below are my top red flag answers followed by ideal answers — and my thinking behind all of it.

 

RED FLAG

I don’t have a good picker. 

Why

Because they’re not taking responsibility for the problems. 

And they’ve decided that choosing the “right” partner is more important than how they show up in a relationship.  

When you have relationship skills you can make it work with anyone.

It’s not about them. It’s about you. 

RED FLAG

We couldn’t communicate.

Why

This one isn’t bright red. More like pink with potential to go in either direction. You need to ask a follow up question to determine which column it belongs in. 

Something like, “What do you mean?” so they elaborate. 

BETTER RESPONSE

“I don’t exactly like serious conversations and neither did she so we just avoided them until the problems were so big we couldn’t anymore.” 

RED FLAG

My ex cheated on me.

Why

I don’t like this response because although cheating is clearly a maladaptive coping mechanism and patently wrong for the ex to have engaged in, it puts all the blame on the ex.

Cheating was a symptom. How do I know? Ask yourself how many fulfilled partners cheat. Exactly. 

BETTER RESPONSE

“It ended because my ex cheated on me. She’d been pretty unhappy for months and asked to go to counseling but work was busy and I didn’t make time.” 

RED FLAG

We grew apart and fell out of love.

Why

Unless one of you is dead, you’re each going to continue to grow. It’s both your responsibility to make sure you stay connected and don’t grow apart. Also, after about the first year or two, partners can’t rely on feeling the emotion of love to engage in loving behaviors. That expectation is unrealistic. You can’t bottle an emotion and freeze it in time. Love, like all emotions, ebbs and flows. When you engage in loving behaviors (dating, seduction, thoughtful words, helping out, little surprises), you keep your partner in love with you which means they’ll likely reciprocate. 

BETTER RESPONSE

We just fell into a groove. We stopped dating and turned into roommates. My therapist says I just expected all the good stuff to keep going. Now I know it doesn’t work that way.   

RED FLAG

I’ve never had a relationship. 

Why

Think through your past relationships. 

They were hard, right? Took a lot of work? 

Now imagine if your exes had never even had a relationship.

No frame of reference for anything. 

No clue how to disagree, or have a fight or make up or compromise. 

 

I don’t want to be someone’s first. 

In anything, quite frankly.