Challenges and Red Flags for Dating a Divorced Man

The truth of the matter is those in the dating pool who are looking for more than a casual, fun (non)commitment will likely find themselves at some point facing a divorced individual on a date. The divorce rate has steadily increased, making that a greater possibility.

While you might realize some challenges with dating a divorced man, and you have to be cautious for red flags, there could be advantages, especially if you’ve never been close to being in a commitment of this sort (like an engagement.)

If it turns into a healthy partnership, the guy can prove to be much more communicative than most of your previous mates, thoughtful and respectful, mindful of your needs, and overall have a greater understanding of how partnerships work.

But that will depend on why he’s now divorced. That’s one of your first challenges, learning why he’s back on the market and what led to the divorce. Let’s look at a few more and some of the red flags you need to look out for.

Challenges associated with dating a divorced man

Divorce is an unfortunate part of life that none of us would go through if it could be helped, and it’s a label no one wants to walk around with. But once you have it, people looking to date find you a challenge.

In some ways, that is a legitimate assessment. Most people who find themselves divorced are cautious, especially about getting back into the dating game. When they do, there will be things that come with them. Let’s look at a few of these challenges.


An ex-spouse will always be part of a husband’s life, and that’s especially true if there are kids in the picture. If there is shared custody, the exes will need to interact quite regularly, plus you will be co-parenting as the dating partner. That also means you’ll be meeting the kids’ mom at some point.

The ideal situation would be to build a relationship with the mother and kids to help the family transition and ease tension.


Getting married again might be off the table for your new mate. He might be of the mindset he’s already been there and done that; he’s not willing to try it again. Of course, after time passes, those feelings can change. But that’s a risk you need to decide if you’re willing to take, especially if you intend to marry.


Once trust is broken, it’s genuinely a challenge to rebuild that even if you’re not the person who was responsible for breaking it. A man who’s been through the trauma of a broken marriage will look at everyone he dates as a possible threat to hurting him.

If you feel this is someone you want to work on a partnership with, you will need to try to re-establish a sense of trust from scratch. So he realizes you’re nothing like his ex but a person who deserves a chance to be loved by him. It will just take time and patience.

Perfect pair

You could find that he is the ideal man for you, but convincing him of that fact can be a job. While divorced partners know better than anyone how relationships work, he’s unsure of his ability to put that knowledge to work because he feels he failed at his first attempt.

While men coming out of divorce have no desire to be alone and developing an exclusive, committed relationship is their desire (without the notion of another marriage), it can prove to be a scary concept as well.


When you meet a person that seems like an interesting, good guy and you go out a few times. But he continues to talk about his ex-wife and the divorce, this is someone who’s not ready for dating.

You question in your mind why this man would be even out attempting to see people when he has clearly not healed. But in many cases, these individuals don’t want to be alone and are genuinely hoping to find a nice person to spend time with.

Red flags associated with dating a divorced guy

When dating someone who is divorced, most single people are focused on the present, what’s happening in the here and now. Seriously, that’s how it should be. But things are different when you see a divorced man.

Many don’t realize this person is still in the past thinking over what used to be and often how this measures up. Not only are you faced with many challenges when you date divorced men. But there are potentially also red flags everywhere that you need to pay attention to.

These could be telling you to run in the other direction with the possibility of you getting hurt. Some red flags or blatant warnings that you need to be mindful of with a divorced guy include:

There is mention of a court date

It’s vital to make sure you’re dating a divorced guy and not a man who is separated. There’s a world of difference between the two. Men and women will develop relationships before they are legally divorced, and that’s a bad place for their new mate to be since there is every possibility that the marrieds will get back together for one.

For two, what kind of respect does that show to the union of marriage. If kids are involved, that speaks volumes to how little marriage means as a covenant.

While separations have the potential to go on merely a matter of months to a couple of years, the sanctity of marriage should be recognized until the decree has been finalized.

Someone stuck in a dating relationship with a “still married” person will suddenly realize that their new partnership has no possibility of leading anywhere.

There needs to be a legal divorce and, after that point, a healing period before he can even consider another committed relationship or want one. So why is he even dating? This is a reason to run, not walk, away.

Still healing

There are stages of grief when experiencing a loss. You want to avoid being someone’s rebound after a marriage ends. It can take people different periods of time to reach acceptance. If you’re dating a divorced man, one of the red flags is if he is still visibly upset at the idea that he’s single again.

That indicates that he is still on the rebound from the marriage. You could be his first foray into dating, and that’s not a good position to be in. In almost every case, the rebound person is not one who lasts.

Vague or dishonest with the reasons for the divorce

While it’s true, it takes two people to make a marriage work and two people to cause it to go downhill, a man will know his part in its decline. Understanding the reasons will give you insight into what he intends for the future, how he deals with conflict, his thoughts on marriage, and so much more.

If there is any sort of hesitancy to share even the slightest detail, or you detect dishonesty, this says much about his character in itself.

It’s not only a red flag when you’re dating a divorced guy; it’s a reason to walk away from him. Even a small lie or avoidance is not a way to establish trust or develop closeness in a partnership.

Constant discussions on the ex

When a partner can’t stop talking about his ex-spouse, that’s a giant red flag regardless if the conversation is attacking the ex or pleasant memories. These are unresolved issues that need to be worked through, whether with the ex or perhaps with a professional counselor. You are not the therapist and don’t want that role.

Too often, it will happen that a divorced person will use a dating mate in the capacity of a counseling partner. The guy will vent all their old marital trouble forgetting this person is a new significant other with no desire to go over their baggage, let alone help with sorting through it.

The ideal way to deal with it is to suggest a counselor work through it, and if it’s not possible to get it sorted, your relationship will need to end.

Final thought

Divorce is difficult, but it’s significantly challenging being the dating partner of a man coming out of divorce, depending on where he is in the healing process.

If you know what red flags to be aware of, you can save yourself some heartache, but many singles end up hurt from their experiences. It can be an unfortunate situation for everyone.

That doesn’t mean every experience with divorced men is terrible. There are some out there who are healed and ready for dating. These guys know how relationships work and offer partners a healthy, communicative, respectful partnership.

You genuinely need to pay attention when you’re in the dating pool among divorced guys, so you don’t get a bruised sample.

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About Rotifoly Editing Team

Our writers share the same interests, which is the passion for writing based on in-depth research and helpful information. We're a team of writers in the social media world, so we know how to deal with common issues on dating and friendship, and we share tips and tricks for everyone.

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