If you’re in your 40s or older, there’s a pretty good chance you’re going to end up dating a divorced man at some point.
This is definitely a horse of a different color from the single young guys you may have dated in the past. So, I wanted to provide you with a video and article to help you navigate the world of getting to know a man who has experience in a long-term relationship…but who also may have his own baggage.
Given that I am a man…but not divorced…I wanted to find you the best expert on dating a divorced man I could find.
It turns out, I didn’t have to look far. My mother, Ann LoDolce, is a divorce attorney, so I tapped her infinite wisdom to help you!
P.S. You’re on a journey right now, and it’s one that will have both joys and frustrations. My How to Find Love After 40 workshop is the perfect guide to help you on your way. Sign up here.
If you’re divorced yourself, you’ll definitely appreciate the fact that things are different than they were when you were single. You may be a part-time parent, have an ex that you still argue with, or even still be reeling from the expense and emotional trauma caused by the divorce itself.
But regardless, you’re looking for love and you absolutely deserve it.
The same goes for dating a divorced guy: he may have a few things that make his life…well…less simple than you’d like, but that doesn’t mean he’s not a great candidate for the role of Mr. Right.
Here are some things you should be aware of if you’re going out with men who are divorced.
1. He Might Be Dishonest About the Reason for the Divorce
On your second or third date with a new guy who’s been divorced, you naturally might ask him what happened in his marriage.
One of three things will happen:
He’ll be totally honest about the reason (“We argued all the time. It was a toxic environment.”)
He’ll be a little squirrelly or vague about it (“It just wasn’t meant to be.”)
Or he’ll fib about it.
I know. That’s not what you want to hear. But my mom, who’s helped countless people navigate the tricky world of divorce, says that it’s a very unpleasant topic for most people, and you’ll often find in dating a divorced man, that he may not want to talk about it at all.
“But you need to know something about how it happened,” Ann says.
You don’t need to grill the guy on your first date, but if it seems to develop into a relationship, you deserve to know about his past experience for one reason: history repeats itself.
If he cheated on his wife or had anger issues, you need to be very concerned about how that might impact your relationship with him. While I don’t like to generalize with the whole “once a cheater, always a cheater“ saying, you have to take the possibility into consideration. Was it a one-time thing during a stressful period in his relationship, or was he a serial cheater?
If his ex-wife cheated on or hurt him, that may make it hard for him to open up to you and trust you fully. Can you handle his suspicion and jealousy?
2. His Ex Will Be Part of His Life
Ann says this is especially true if children are involved. If you’re dating a divorced man with kids, you’re dating the whole package…including, to some degree, the ex-spouse. If you end up living with him, you’ll likely be sharing custody of those kids and will have to co-parent with both your boyfriend and his kids’ mother.
You may even have to meet the ex at some point, which, while no fun, can help to establish a relationship with her and her children. This can make the transition to this new family dynamic a little easier.
Try not to be jealous of their relationship. He’s moved on from her and is with you. He will need to talk to her if they’re sharing custody of the kids, and that may take some getting used to. Allow time to adjust to this.
And if she’s overstepping, talk to him about establishing boundaries. Maybe she texts from the car when she arrives to pick up the kids rather than walking into the home you share.
3. He May Not Want to Get Married Again
When you’re dating a divorced man, even if he’s head over heels in love with you after a few months, you have to be aware that he may never want to get remarried.
If the divorce was messy, that may have traumatized him to the point of believing he never wants to go through it again. Of course, you’re thinking if you did get married, you wouldn’t get divorced, but he’s playing it safe and protecting his heart by shutting out the possibility of marrying again.
There are a few paths you can take here. If you’re okay being in a long-term relationship without being married, great.
But if you dream of marrying a guy like this, you can either be patient and hope that he eventually heals from his divorce trauma and decides you’re the wife he always wanted…or if you think he’ll never change his mind, you can let go and move on.
4. He Could Be Jaded About Relationships Altogether
“Sometimes the divorce makes it very difficult to trust, and the person might be seeing only the worst in everybody around him for quite a while,” Ann says.
This can be tricky. Sometimes we bring our past relationships into our new relationships. It’s baggage. You might have some of your own, I’m guessing.
Be aware that you may have your work cut out for you. If he’s genuinely worth it, start building trust from the start. Work to show him that you’re not his ex. That you’re someone entirely different and worthy of his trust and love.
He needs to—and will—be open to a new relationship, but it may take time, so have patience.
5. He Could Be a Great Match!
Ann says that just because a man is divorced doesn’t mean he’s flawed or damaged. Sometimes relationships end, even after marriage vows and decades. If he learned about himself and about relationships in the process, then he could be great relationship material for you.
As you get more dating experience under your belt, you’ll meet men who have never been married or who haven’t even been in a serious relationship longer than a few months. Conversely, dating a divorced man lets you know that at least he understands how marriages and relationships work, and more than likely he’s had to compromise, communicate, and work at a relationship.
All good things for you, Sexy Confident lady!
6. If the Divorce is Fresh, He May Not Be Ready to Date
If that’s the case, you’re wondering, why is he dating?
Maybe his friends are pushing him to “get back out there.” Maybe he wants to find his confidence again. Maybe he’s just looking for sex. But if he’s not ready for a relationship, you’ll never convince him otherwise.
So…how do you know if it’s too soon?
Ask him when he got divorced. If it was within the last couple of years, just tread lightly. Pay attention to whether he talks about his ex often (either wistfully or angrily; either could indicate he still has unresolved issues.).
If he’s only separated and not fully divorced, try to keep things light. The last thing you want to do is fall in love with a man who isn’t 100% available.
7. If He Has Kids, They Take Priority
If you have kids yourself, you totally get this. If not, you may feel like you’re vying for his attention when he’s focused elsewhere.
You won’t win that competition. He rightfully should be focused on his children, especially if they’re still healing and getting used to the post-divorce situation.
Wait as long as possible to meet his kids. Like, until you’ve exchanged the “L” word. Not only do you not want to enter these kids’ lives if there’s a good chance you’ll also be exiting soon, but you also don’t want to get attached to them and then have things not work out.
8. He May Be a Serial Monogamist
This isn’t flattering, I know, but some men are serial monogamists, moving from one long-term relationship to another. He may miss the stability and comfort of being married and may be looking for a relationship just to catch that vibe again.
It can be hard to spot a guy like this because you want a relationship too, and here’s a guy who seems keen to settle down with you. But if you don’t feel a 100% connection or things just seem off, despite him wanting to dedicate more and more time to you, realize that he may just want his next relationship, regardless of whether you’re the right fit or not.
9. He May Just Be Looking for a Warm Body
The converse is true, too. He may be on the opposite end of the spectrum, looking for nothing more than casual sex. After all, he was in a relationship for years or even decades. Now he’s ready to play!
If you’re aligned with this, then good luck to you. But if you’re hoping that your weekly hookups turn into a relationship, I’m going to say that you’re probably barking up the wrong tree. Find a man (divorced or otherwise) who is ready to commit to you.
10. He’s (Probably) a Responsible Human Being
If you’ve dated men who live in bachelor pads that look like they probably did 20 years ago…
…men who can’t cook anything other than ramen…
…and men who run at the first sign of emotional intimacy…
…you’ll be delighted at what you get when dating a divorced man. He knows how to set up autopay for his bills. He can make a mean chicken cordon bleu. He’s on track to retire early. He can even French braid his daughter’s hair.
This guy may restore your faith in men simply because he is one. He’s not a manchild or Peter Pan. He takes responsibility for his actions. He knows how to communicate in a relationship, open the door for his lady, and admit when he’s wrong.
Whether you’re divorced yourself or have just kissed a lot of the wrong frogs over the past few decades, remember what you’re looking for as you’re dating a divorced man.
“Be sensitive to your own needs, as well as his needs. It’s very, very important to keep in mind that you count as well as his needs,” Ann wisely says.
He may take more patience and effort than you expect, so make sure he’s truly worth it. Because trust me: you definitely are worth patiently waiting for the right guy for you!
Talk to me in the comments below: are you dating a divorced man? What issues or concerns have come up for you? What benefits have you seen?
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