Skip to content

Make Or Break Questions to Ask a Divorced Woman on the First, Second, and Third Dates

Make Or Break Questions to Ask a Divorced Woman on the First, Second, and Third Dates

Make Or Break Questions to Ask a Divorced Woman on the First, Second, and Third Dates

The beginning of any relationship is akin to walking a tightrope.

Any sudden movements or slip-ups might well result in the death of this fledgling relationship.

With each date you go on that tightrope becomes a bit wider.

But before we can start dreaming about successful relationships we need to first get past the most precarious stage of the relationship.

While any nascent relationship calls for a certain level of tact, these fresh relationships also call for probing questions.

No more dynamic is in need of these questions than when you’re dating a divorced woman.

In this article, we’ll teach you how to walk the tightrope while using tact to ask probing and stimulating questions.

In this article, we’ll break down questions to ask a divorced woman on a first, second, and third date.

But first, here’s Mayim Bialik with five things you should never say to a divorced person.

Questions To Ask A Divorced Woman On A First Date

First, a warning. Divorced people are used to labels, stereotypes, and getting treated a certain way by insensitive and ignorant non-divorcees.

Don’t be one of these people.

This is not an interrogation nor an opportunity to exoticize this person.

Foremost it’s a chance to get to know someone on an intimate level to see if there’s any chemistry. That’s the purpose of every first date.

The main reason you’re asking about her divorce is to:

1) Find out if she’s emotionally ready for a relationship

2) To learn about her attachment style

3) Understand her current relationship with ex (learn about red flags)

With that being said, let’s get started

Fist Date Questions For A Divorced Woman

If you’re following MegaDating guidelines, first dates will be less than one hour and involve spending less than $10.

This doesn’t allow much time for questions about prior relationships.

This is why you should keep the line of questioning light during the first date.

Your job is to form a little chemistry and figure out if this person is your type.

To do so, consider asking some of the following questions that have absolutely nothing to do with her marital status:

— What’s your biggest pet peeve?

— What did you study in college?

— What song always makes you dance?/What’s the last song you played on Spotify? (Ask to see account)

— Did you pick up any new hobbies during the pandemic?

— You go to the Caribbean on vacation – do you take a cruise or book an Airbnb on an island?

Remember that none of these questions should be random. They should all be organic and seemingly fit into the vibe of the conversation. That rule applies to divorce and non-divorce-related questions alike.

As far as divorce-related questions are concerned, here are a few you might consider asking on a first date:

— Tell me about the last place you and your kids traveled to.

— How often do you see your kids/do they live with you?

— What’s your favorite childhood memory?

These types of questions show how family-oriented she is and of course, will give you some insight into her family situation growing up. You don’t want to get TOO DEEP with her on a first date. So very subtle questions are best that don’t rip into deep wounds.

Questions To Ask A Divorced Woman On A Second Date

Now that you two have built a nice little rapport it’s time to put a bit more weight behind that accelerator.

Again, the main purpose of this date is to enjoy her company and continue to see if you two are a match. Learning more about her divorce should be a natural byproduct of the date.

As you ask questions it’s only natural that her divorce will come up.

When that happens be sure to ask a few of these questions:

— Why didn’t it work out?

— How long did you know each other beforehand?

— How’d you meet?

— Are your parents still together? 

— How long have your parents been married?

— Are they happy?

It’s best to start bringing up a little deeper questions on the second date, especially on a physical type date where the good vibes are flowing.

The second date should be different from the first in two ways.

One, second dates have no time restrictions.

Two, second dates should be active.

I’ve always felt that it’s easier to have a conversation when being active.

Your adrenaline is pumping and dopamine is rushing through your body as you’re bonding with your date.

Some quality second date ideas include:

— Hiking

— Bike ride

— Scenic jog

— Mini-golf

— Frisbee

— Ice skating

— Dance class

— Farmer’s market

— Climbing gym

These dates are all conducive to having a deep conversation. During or after the blood-pumping activity, strike up a conversation that’s a bit edgier and deep than the topics you covered on the first date.

Questions To Ask A Divorced Woman On A Third Date

If she’s lucky enough to make it to a third date it means you might be up for dating her in the long term.

That being said there are a few make or break questions you’ll want to ask before planning your future.

Here are those make or break third date questions:

— Would you ever remarry?

— What would you do differently the second time around?

— Do you want (more) kids?

— When did you know it was really over?

— Did you have any hesitations before you got married?

— What did you learn from the experience (about yourself) (about others)?

These questions are best asked when spaced out. They also shouldn’t all be asked. 

Look, this woman has gotten grilled before about her divorce.

The last thing she wants is an interrogation or to feel like whether you see her again is predicated on her answer to these questions.

Honestly, your future should more so depend on how you feel when you’re with her rather than how her divorce ended.

What You’re Looking For When Asking Divorce Questions

Why even ask these questions in the first place?

I mean the divorce rate still hovers just below 40% so should you really care that much if someone is divorced?

With the median age of a first divorce in the US for women being at 28, rejecting all divorced women would considerably shrink your dating pool.

The reason you’re asking the aforementioned questions is to primarily look for red flags.

If she still into her ex, was it her fault the relationship ended, does she have poor communication skills, etc.

These are the red flags you’re looking for.

I’m of the mind that most divorces should be viewed as nothing more than a breakup.

We don’t look at someone that just got out of a lengthy relationship with a boyfriend with the same stigma we do with divorcees.

Why is that?

Because we’ve been taught that marriages are sacred.

We’ve been taught that getting divorced is the most traumatic thing that can happen to someone.

While there are grains of truth to both statements, everyone’s divorce is different. They don’t let themselves be defined by it so why should you?

Unless this person is emotionally scarred or warped to the point that you think it would significantly impact your relationship, you should give them a chance.

Why You Should Give Her A Chance

Paradoxically perhaps we should begin to consider divorcees a label or strength rather than one of weakness.

Those that initiate a divorce have the balls to tell the world — or rather those they said “till death due us part” in front of — that they were wrong. That even though it’s messy, sad, and potentially more destructive than a wildfire, some relationships (no matter how intricately they’ve woven together) must come to an end.

It takes strength and recognition to ask for a divorce.

I say divorce is like a wildfire for two reasons.

On the one hand, it burns bridges, relationships, and tears down everything you’ve been building since you met this person.

But what happens after a massive wildfire?

It allows someone the chance to begin anew. New plants now have the chance to grow where once before another tree was blocking their access to light. Destruction causes new growth and the chance for drastic change to take place.

Tips For Dating A Divorced Woman

If my little speech touched a nerve and convinced you to give her a chance, there are some tips for dating a divorced woman you’ll want to keep in mind.

Her Kids Are A Priority

You might think that now she’s single she has tons of time to date around.

That may or may not be true, it all depends on her kids.

If she doesn’t have them, great!

If she does, get used to being put in the backseat.

Look her kids will always take precedence over her new man. Get accustomed to the new pecking order.

Be Ready To Take Things Slow

She thought she found the man she’d spend the rest of her life with.

Before tying the knot they dated for years and lived together before getting engaged.

Despite taking her time she realized that just because you get married to someone doesn’t mean you’ll love them forever.

Even if you take things slow it may all come crashing down sooner or later.

With this mindset, you can understand why she wants to take things slow. She may not want to immediately get physical, spend all her time with you, or move in together.

She has some hang-ups (and for all the right reasons).

Be aware that you two might be operating in two different gears. To understand where her head is at check-in with her and ask her what her thoughts on the relationship are.

Be What Her Ex Wasn’t

As you become closer she’ll start to open up about her ex.

She’ll tell you all the reasons why it went wrong.

Listen to her when she reveals all the wrong turns that led her towards divorce. When she talks about trust, money, sexual, or emotional issues she had with her ex, listen and learn.

Always keep an ear open, remember what she says, and strive to do the opposite of what her ex did.

Just Be Awesome

Show her that there’s a reason to start dating again.

Be lively, spontaneous, sexy, consideration, caring — be all the adjectives she wants you to be.

It can be difficult for her to shed her leery skin and celebrate being in a healthy relationship.

She may need space and time to think, so be prepared to give it to her.

But above all, just be an awesome guy that she’s happy to see.

A Question For You?

Now it’s time that you ask yourself a question.

Are you ready to date a woman that might have some emotional baggage?

What about a woman that has kids?

Seriously ask yourself these questions before jumping into a relationship with a divorced woman. Not knowing what you want beforehand is a great way to waste both her time and yours.

If you still don’t know what you’re looking for, talk to us — we’re experts.

Comments are closed for this article!

Featured Articles