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Dating a young divorced man is, in many ways, very similar to dating a young man who has never been married. They can have various levels of maturity and may or may not bring baggage to a relationship.

However, there are some specific tips that can help you figure out what is going on in the mind of a young divorced man.

These tips can help you identify some red flags that wouldn’t come up in a relationship with a man who’s never been married before.

Here are ten tips to help you figure out if this divorced man is a bingo or a bust:

concerned woman

1. Know Before You Commit

As you’re making small talk and getting to know each other, you’ll probably find out he’s divorced on the first date. 

There’s no reason he shouldn’t mention it if it comes up, but as you’ll see below, you don’t need all the gritty details just yet.

Resist the urge to ask what happened, but don’t get emotionally or physically invested in the guy until you know what happened. 

It’s OK to be attracted to him, even to start liking him quite a bit, but you need to protect yourself from some possible heartbreak if it turns out he’s still “damaged goods.”

If you think you like him, put the divorce aside for a bit. You can go on a second or third date with him if only for the reason of getting to know more details later. 

If having sex with him will form too much of an emotional attachment with him, hold off for now.

how to date a young divorced man first date

2. Don’t Ask On Date One

Once you hear about the divorce, you’ll probably have a nagging urge to ask for details, and he’s probably going to feel awkward if he doesn’t share more. 

You should resist the urge to ask, and if he starts to explain, give him a little wink and tell him that’s for a “later date.”

The purpose of a first date isn’t to share or sniff out dirty laundry. The purpose of a first date is to get a second date. 

Even if he reveals he’s divorced, don’t ask about it until you know you like him (but not too much). 

It's possible you end up not liking the guy after the first date and you won’t want to see him again, so it won’t matter why he got divorced. 

If you like him an appropriate amount when you ask him, you’ll be willing to genuinely listen to his story without looking for red flags.

If he absolutely insists on giving you the whole story on date one, he’s probably an “over sharer.” 

This could mean he’s insecure about it, still mad, or lacks appropriate boundaries, and could be a warning sign.

new couple discussing bills

3. Watch His Communication

Communication is important in any relationship, and people who have never been married can have poor communication as well. 

Still, young men who have been divorced often have certain types of communication to watch out for. 

When you’re considering how to date a young divorced man, listen for these communication red flags:

Blaming others. If you notice him blaming you or others without acknowledging the blame he shares, it’s a huge red flag that you’ll never be able to communicate what you need from him, especially if it’s an apology.

Overly Sensitive. If he’s overly sensitive or insecure (over apologizing, quick to anger, or always criticizing you), it’s a red flag that you’ll never have the intimacy with him that you need. He can’t be vulnerable, so your relationship will always be superficial.

Secretive or Avoiding Questions. At best he’s afraid of being vulnerable or being intimate. At worst he’s hiding something. Maybe he’s shy, so give it some time. But if it’s a consistent pattern, it might give you an idea about why he’s divorced.

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4. Watch His Mental Health

There’s no denying that divorce can come with a lot of emotional weight. That’s to be expected. 

But that doesn’t mean you want to get involved with someone still dealing with that. If he hasn’t dealt with his divorce, he may suffer from unresolved depression or anxiety.

The following are signs that he’s more than you can handle right now:

Lack of Interests. If he doesn’t seem to have any interests or won’t talk about them, he may be dealing with some depression. Men who are recently divorced, especially young ones, should be relishing in their newfound freedom and discovering new passions.

Not Eating. How much does he eat during your dates? If you’ve been with him a while and he just picks at his food or doesn’t eat much, it could be a result of his divorce.

Cancelling. Does he cancel on you a lot even though you know he likes you? This is sure sign he’s dealing with some difficult issues and either doesn’t have the energy to go out or is scared to let you find out.

Oversleeping. Does he have difficulty getting out of bed? Does he sleep too much? Is he always tired?

Maybe you’ve been with him for a while now and care enough to put in the effort to stick it out. But if it’s early in your relationship, consider taking care of your mental health by moving on.

how to date a young divorced man consoling woman

5. Respect His Feelings

He might have a lot of feelings, even if he’s mentally stable. He may be overly sensitive or be more comfortable than usual being vulnerable, or even crying. 

These are GOOD traits for men to have. Don’t fault him for it, and for the early stages of the relationship, try not to do or say anything that will hurt these feelings.

At the same time, you may be in a position to help him work through his feelings if you’ve been with him for more than a few dates. 

If you’ve learned the whole story and are sticking around for a while, you could really help him!

Encourage him to talk about whatever he needs to and promise not to judge, or even to give advice. 

If he knows you’re at a stage in your relationship where him just venting won’t drive you away, it’s going to do great things you two and help him heal faster.

woman looks out a window

6. Figure Out Him And His Ex

When you’re deciding how to date a young divorced man, you need to figure what his relationship is like with his ex.  

Are they still on good terms? Does he hate her? Are they “best friends?” What he says will give you some insight.

If they’re still on good terms, but not best friends, it’s the best possible scenario for you. It means that neither of them damaged the relationship too much. 

He’s probably very emotionally mature and will be able to have a wonderful relationship with the right woman.

If they’re “best friends,” it might be OK, but could also be awkward or tense. He might not have unresolved feelings for her or try to get her back. 

But he’s never really moved on, even if he has kids with her. You’ll probably always see her as competition or be compared to her. The good news is, he’s probably relatively mature.

If he hates his ex, he might have good reason, but it says a lot about him. 

One or both of them really destroyed the relationship, and more importantly, he hasn’t been able to forgive her. 

Many times, we’re attracted to, and attract, the people who are most like us. It’s likely this guy is a serial divorcer in the making.

how to date a young divorced man sad woman

7. Notice How Often He Talks About His Ex

One thing you’ll want to take notice of is how often does he talk about his ex-wife, his marriage, and their divorce. 

If he talks about it during the first date, and talks about it a lot, get the heck out of there. 

He’s not over it, he’s not over her, and though he may be a good guy, he’s not ready for another relationship. 

If he refuses to talk about it or is not very forthcoming about details even when you ask and want to know, it’s another red flag. 

He’s really not over it, may still be struggling with some emotional issues, and could have a whole host of other problems that will surface later in your relationship.

The best situation is if he volunteers genuine, emotionally forthright information when appropriate, or when asked. 

This means he can talk about it without too much emotional turmoil and has mostly moved past it and it doesn’t rule his life. 

He’s ready for another relationship, even if not everything in his life is resolved.

couple sits apart on a couch

8. Find Out If He Hates Women

If you’re considering how to date a young divorced man, you need to figure out how he feels about women in general, not just his ex-wife. 

It’s an unfortunate truth that sometimes divorce makes men hate women…

In many cases, especially if the woman was primarily at fault, his anger at his ex-wife is justified and understandable.  

However, that anger should never translate to hate, even for a woman who hurt him, and especially for women as a whole.

A man who’s allowed one bad relationship to sour his view of an entire sex has serious issues. 

He’s an angry individual and eventually he will take anger out on every woman in his life. This also likely means he’s not able to take responsibility for his own failings.

But I shouldn’t have to convince you that hating women is a bad thing. How do you know if he does?

How does he talk about women? Does he talk about them like they’re objects or that they owe him something because he’s male? Is he smarter than every woman or never wrong? 

Does he make inappropriate sex jokes about women, or even just comment solely on their looks rather than other qualities about them?

How does he act around women? Does he interrupt them or ignore them when they’re speaking? Is he overly handsy or doesn’t ask for consent? 

These are all signs of toxic masculinity and demeaning attitudes towards women. Run far, far away…

couple talks in a kitchen

9. Know If He’s Forgiven His Ex

If you want to figure out how to date a young divorced man, you need to figure out if he’s able to forgive people who wrong him. You need to find out if he’s forgiven his ex-wife.

Maybe he hasn’t had enough time yet, which is OK, but he’s probably not ready to date in that case. 

If he’s working towards forgiving her, and it’s obvious he’s doing well in that regard, it says a lot about his character. It’s likely that even when you fight with him, you’ll get through it.

If he hasn’t forgiven his ex, or isn’t even interested in doing so, it’s another warning sign like what I’ve mentioned before. 

He’s not emotionally mature, he’s not interested in making a relationship work, and he probably doesn’t communicate well.

how to date a young divorced man hugging couple on beach

10. Establish If He Can Change

Changing and growing as person is essential for any healthy relationship. 

People who can’t commit to changing for the better destroy their relationships, or at the very least allow them to grow stale.

In almost every divorce, both parties are to blame, even if it’s just that you got married too quickly or picked a bad partner. 

Because men who haven’t been married don’t have the same experience from which to draw, a divorced man is in a unique position for immense personal growth.

Does he capitalize on that opportunity? Can he express how his divorce has changed him for the better or what he learned from it? 

If he can, he’s likely a great person to be in a relationship with.

Can he admit whatever fault he has and whatever role he played in the divorce? 

If he can’t, if he thinks it was 100% the fault of other people, eventually that blame will fall on you when something goes wrong.

Does he have high expectations? That’s OK and can be a benefit in a relationship. But what does he do when those expectations aren’t met? 

Does he get angry, accusatory, or depressed? Or is he understanding and encouraging to the person who didn’t meet the expectations?

Knowing how to date a young divorced man is a completely different game than men who haven’t been married. 

These are some of the tips to helping you figure it out know if there may be potential for a happy, healthy relationship.

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