Relationship Roulette: What To Expect When Dating A Divorced Man

October 18, 2012  |  
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With divorce rates what they are, the chances of you falling for a divorcee are getting higher and higher. There’s been a surge of people that married in their early twenties, when that was the trend, realized in their forties they didn’t know who their partner was, or who they even were themselves, divorced, and are now looking for a new, more informed type of love. So what are you in for when dating a divorcee? He comes with the experience, but also the pain, of a married man. Here are the pros and cons.


You can see his Ex everywhere

Even if his ex lives in another country, you can Google her, Facebook her, Twitter her, Instagram her…and unless you’re an individual of extremely strong will power, you will do all of those things. And doing those things is a form of self-torture. He loved this woman in the ultimate way once, by making the decision to conjoin lives with her. And then, he rejected her in the ultimate way, by divorcing her. You’ll obsess over anything you learn about her. Is she different from you? The same? Is that good? Is that terrible?

They (might) still have to talk

No matter how great the lawyers, there are still plenty of loose ends after a divorce. She needs the number to the handy man they used. He needs to give her dad back the golf set he lent him. The possibilities of reasons they need to get in touch are endless. And every time they have to talk, he will hurt a little more all over again. And you’ll need to console him.

He will always hurt

Loose ends aside, there will always be a place in this man that hurts over the divorce. Divorce can feel like the biggest failure to a person. Something they thought they were 110% certain about, they turned out to be wrong about. It is disconcerting, confusing and very painful. There’s a seriousness that divorcees inevitably carry. They will never be as hopeful, as positive, or as big of dreamers as the man that’s never married. They’re a little jaded, whether they like it or not.


His parents will be tougher than ever

You think his ex had a tough time winning over the parents? You’re the one that will really struggle. You don’t have to be good enough for any old guy. You have to be good enough to heal the wounds of a divorcée. You need to seem like a foolproof, 120% guarantee, sure-thing woman. They will seek out flaws in you that they didn’t seek out in the past women they dated.

His friends will be more protective than ever

His friends, even if they are sweet and welcoming to you, will have a certain undertone that says, “Be careful with him…” They will probe any story you tell them about yourself, or about you and the guy, extra carefully to make sure you really care about him. You’ll be aware of being watched always.


He may not want to marry again

Some men only want to marry once in life. If your divorcée has been divorced multiple times, the chances of him wanting to marry again are ten times slimmer. You either have to be okay with not marrying, or you have to be prepared for the long battle of winning a guy over again, that has become disenchanted with the idea of marriage.

He might not know how to date

If he was married for a long time, it’s been a while since he had to court a woman! He may take things very slowly for fear of messing up, or far too rapidly because he’s used to having a close relationship. He will be a little rusty, and a little awkward.


He knows how to commit

The guy clearly doesn’t have a problem with the idea of monogamy since he did at one point agree to be with just one woman for the rest of his life. Certainly many divorced men just want to be alone for a while after divorcing, but once a divorcee is out on the market and dating, it’s usually because he wants a close relationship again.

He knows a thing or two about relationships

He learned by the biggest trial and the biggest error what makes relationships tick. He probably knows how to communicate and compromise more than any of his never-married buddies. He knows how to incorporate somebody else into his life. He’s overcome that selfish, “everything is about me and what makes me happy and successful” phase all men go through at some point.

He knows a thing or two about himself

Nobody comes out of a divorce without doing some serious self-reflection, and perhaps some therapy. He probably isn’t afraid to look within himself, and figure out when he can do things differently and what he needs to work on. In other words, he has probably figured out what parts of the divorce were “his fault” and will pay close attention to that in future relationships.


He doesn’t have a space issue

He’s over his bachelor mentality. He won’t freak out if you leave a toothbrush at his place, or bring over some books to read while he is working. At that point, he probably won’t freak out if you just want to hang out at his place for hours upon hours, while he runs errands or works.


He knows what he wants

After the major pain of a divorce, he took some serious time to analyze all of his past relationships, and understand what he wants in a woman. So if he’s with you, he wants you. He understands what he likes about you. He’s less likely to suddenly disappear, like many guys do, when they suddenly find something they don’t like about you. He is far more perceptive from the beginning, so less surprises him.


His finances have probably shifted

He may not be broke, but if he was super loaded before the divorce and now he’s worse off with good reasons, it probably took a toll on his mentality about finances. If he did have to give up a lot in the settlement, he might be very wary to spend money on you in the beginning before he knows he can trust you.

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