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How to Discuss Your Tricky Divorce To a New Woman You’re Dating

How to Discuss Your Tricky Divorce To a New Woman You’re Dating

Discussing your divorce to a new woman you’re dating is as the title of this article suggests, tricky.

Divorced men at least believe there’s this stigma around them. They think that they’ll be judged harshly for saying till death due us part only to skip out before you’re in the grave.

It’s true that while some will, most won’t.



Most women won’t see red flags just because the man she dates just revealed that he’s divorced. Times have changed and divorce is more commonplace than ever before with about 50% of marriages ending in divorce.

After you tell her you’re divorced she might be skeptical and a rush of thoughts might hijack her mind. But remember, she was skeptical of you before she knew about your past relationship. Women (and men) are naturally skeptical of getting to know a potential mate.

It’s what we do.

The fact of the matter is that women do date divorced men. Arguably divorced men have many qualities their non-divorced counterparts don’t.

That being said how to discuss your divorce with a new woman you’re dating can have a massive impact on the relationship going forward.

There are tactful ways to talk about it and not-so-tactful ways.

To pave the way for a beautiful relationship to take shape let’s learn how best to let her know that you’ve divorced and that you’ve moved past this epoch.

how to discuss your divorce with a new woman you're dating

How To Discuss Your Divorce With A New Woman You’re Dating

Let’s set the scene.

You’re divorced but you’re still in court and involved in messy custody battles.

Your ex is furious and willing to attack you in any way she sees fit and that includes potentially women you’re dating. Not only that, the legal fees are piling up and even though you have a solid job, you’re nowhere near where you’d hoped to be because your ex just won’t let legal proceedings end.



So how do you bring this up to the woman you’re dating and when should you talk about it?

My first piece of advice, don’t emotionally vomit. 

Keep Your Ex-Wife and the Woman You’re Dating On A Need-to-Know Basis

These are trying times.

It’ll be tempting to unload your troubles on the new woman you’re dating. The moment you feel you can confide in her you’ll have an urge to lay out all your dirty laundry.

But don’t.

Find a friend, family member, or therapist to talk with if you need to vent.

Look I’m not saying to never speak a word of your divorce to the woman you’re dating — on the contrary.

Rather be selective with the information you choose to share.

Neither party needs to know every detail of your life, especially not the parts you should be kept private.

The woman you’re dating doesn’t need every detail of the gloom and doom you’re going through in court, just that you’re putting in every effort to keep your child safe, happy, and healthy. You shouldn’t be discussing with her the nasty details of the divorce, but by date 3, she does need to know you’re going through a custody battle.

This is because by date three the two of you have built up significant rapport. If she’s worth seeing three times it’s because you could envision a future together. If this is the case, eventually your beautiful new budding relationship will come crashing into your home life. Before these two things unexpectedly crash, give her fair warning and let her in on the situation.

How to Frame the Custody Battle Conversation

You are the narrator of this story.



She’ll only ever see your situation through the lens in which you present it.

You could break down and start crying, venting about how horrible your ex is.

Or you could lay out the cold hard facts of the matter and assure her that your kids mean everything to you and that you’re willing to fight to the end. You can also assuage any doubts she has that you’re not ready for a relationship.

A thought will pop up in her mind that you don’t have the emotional space to invest in a new relationship.

Make her feel secure in this budding relationship by telling her how you feel about her and that you look forward to seeing her all the way. That you haven’t been so excited to jet from your office and rush to see someone after work for decades.

She’ll be flattered that despite all the chaos in your life you’ve somehow been able to develop feelings for her.

Avoid Venting

You can vent to your therapist but I wouldn’t vent to the woman you’re dating.

It isn’t her burden to bear and it will push her away if every time you hang out it’s a huge vent-fest.

This is especially the case if you two only just started dating. The beginning of a relationship is often the most beautiful and most fragile. One wrong word, one misplaced hang, one sub-par date and it can all be ripped to shreds.

I know it will be difficult but try to keep things positive when going out with her. Focus on the beautiful, amazing woman across the table from you and be thankful that you may have a bright future ahead of you.

As far as venting techniques go I recommend journaling.



Carry a journal (could be in notes on your phone) and when you feel the need to vent, go to the bathroom and write it down in your phone.

Then when you have time alone, try screaming into a pillow to release the pent-up energy you’re feeling. Phone a friend or family member or talk to a therapist when possible. 

Remember, the women you date are not your therapist and it’s not fair to unload a ton of heavy custody battle information on them. Avoid going in circles about how unfairly you’re being treated by your ex. That’s between you and her, your legal team, and hopefully your therapist too.

how to discuss your divorce with a new woman you're dating

Keep Custody Discussions Vague, Brief, and Productive

If you have to talk about it, keep your answers short and sweet. Talk about the ideal outcome and try to transition the conversation as soon as possible.

Of course, if she asks do not dodge questions unless you really do not feel like talking about the situation. If you’ve been dating for a while and she is receptive to talking about it, oblige both you and her.

A healthy and productive conversation with someone you’re seriously dating might include creating a list together of must-haves that you can plan for when you do go to court.

However, at least early on in the relationship try to keep things brief and focused on more enjoyable topics.

Avoid Disparaging Your Ex (Even if She Deserves It)

It will only make you look bad to talk negatively about your ex.

If she’s exhibiting personality disordered traits, speak to the fact that she’s just not mentally stable enough to take care of your child.

You don’t need to go into extreme detail. Just explain that your number 1 priority is the well-being of your child and you wish her well.

That should be the focus of the conversation. Talking about a woman she doesn’t know and disparaging her will only serve to make you look bad. At the very least avoid name calling and talk specifics to illustrate what a monster she is.



Although again, it’s best to avoid talking down about people. Rarely if ever is this attractive.

Go On Awesome Dates Where You Don’t Need To Talk

The best way for how to discuss your divorce with a new woman you’re dating is to discuss it and then walk away from the conversation.

After you’ve discussed the divorce and custody battle on a previous date she may be wondering if you’re really ready to date. She may want to back off and give you the space she thinks you need.

Address these fears by taking her on an amazing date where you two don’t discuss the hardships you’re going through.

If this sounds impossible to do, pitch her a date using a TDL that isn’t based around conversation. Instead, have the date revolve around the super stimulating activity you’re doing.

Some date ideas that satisfy this criterion include:

  • Yoga + ice cream
  • Scenic bike ride
  • A nice 6-mile loop of a hike with amazing views
  • Hitting the dog park
  • Bowling (a classic)
  • Barcade
  • Live music
  • A sporting event
  • Just get lost in a movie together then discuss afterward

If you’re worried about vomiting out your situation on a date, just pick a date idea that gives you two plenty to talk about. One that takes your mind off of the situation at home and allows you to enjoy life again.

It’ll be great for your mental health and budding relationship.

Moving Forward

Part of moving forward means finding a new partner.

If you’re reading this clearly you’re ready to date again.

But as you’ve realized, dating during divorce can be a tricky process.

In my men’s coaching program, Dating Decoded I teach men how to meet women IRL and online. I teach them how to find, court, and ultimately build a meaningful relationship. Part of my program focuses on IRL attraction and what you need to do to make her feel comfortable around you.

My full-service lifetime style coaching program (online curriculum, weekly strategy sessions, private student only community, mock dates) can help you skillfully navigate this new dating landscape.



If you’re interested in moving your dating life forward, apply for my coaching program so we can get to learn a bit more about your romantic goals and how Dating Decoded can help you achieve them.

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