Question: “How do you ask if a guy is ready for a relationship if he is ripe off of a five-year relationship?”

This is a question I received recently, and I get some form of the “How do I know if someone else is ready?” question quite frequently.

My response:

“People are notoriously bad at self-assessing their readiness. The only way to really know is to date him and find out for yourself. If you want to.

"Sometimes we think we are ready and we’re not. Sometimes we think we are ready and we are (regardless of prior relationship status/timing). But generally, no premature question out of context will give you the information you need. Time will.

"Even if someone, just out of a relationship or not, is perfectly ready for a new relationship, it still does not mean they are ready for one with you.

"I know everyone wants to ‘not waste time,’ but truly the only way to see if you’re compatible with someone is to take the required time to figure it out. I don’t consider that a waste. I consider it dating. We can’t microwave relationships.”

All too often, I hear stories of people asking extremely personal questions on first dates:

- When was your last relationship, and how long have you been single?

- Why did you get divorced?

- What are your intentions (with me)?

- What is your custody schedule?

I certainly understand the curiosity, but, perhaps against popular advice, I don’t recommend asking any of these questions. Rather, I want you to go into a first date simply hoping to get to know someone new and see if you have rapport. If you leave that date having learned nothing but knowing that you laughed, felt good about yourself, and have a curiosity about the other person, that’s enough for now.

I never consider a date a waste of time, even if you’re ultimately not a match. Attempting to suss out the “important” information in order to disqualify people is not how I recommend dating. Instead, I want us to look for reasons to include people, not exclude them.

The idea of “not wasting time” is a common theme in dating, and it makes sense. People are busy, emotionally cautious, and ready (or even eager) to find clarity in their love lives. But when we focus too heavily on efficiency, we lose sight of the fact that most relationships unfold gradually, and compatibility isn’t something you can uncover with a checklist or a series of rapid-fire questions, especially in the early stages.

What does “wasting time” really mean in the context of dating anyway? Is it spending a few hours with someone who doesn’t end up being your forever partner? Or is it staying in a dead-end relationship for years because you ignored red flags early on? I’d argue the latter is the real time-waster, not the former. Short-term experiences, even when they don’t lead to long-term relationships, teach us valuable lessons about ourselves, our preferences and our boundaries.

Also, taking time to date someone and see where it leads isn’t a passive act—it’s an active choice to invest in the possibility … of a partner and of love. That’s a choice worth making, even if it doesn’t work out. Every interaction shapes your understanding of what you want and need in a partner, and that clarity is never a waste.

So, if you’re wondering whether someone is ready for a relationship, remember that the answer generally won’t come from asking a direct question. It will come from observing their actions, their consistency, and their capacity to show up for you over time. It will come from seeing how you feel when you’re with them—secure, valued, and understood—or not. And most importantly, it will come from staying curious, open and willing to embrace, or at least accept, the uncertainty that dating brings.

Instead of asking them, “Are you ready?” try asking yourself: “Am I willing to find out?”

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