Dating A Divorced Man In His 50s

If you are a woman in your 20s, or even 30s, dating or a divorced man in his 50s may seem like an odd choice. He’s older than you are and has been through something difficult in his life–it’s easy to assume that he’ll have no interest in starting up another relationship.

Dating A divorced Man In His 50s (13 Facts to Know)

But if you take time to get to know this man, there are many things you’ll discover that make him completely unique from every other guy out there:

1. He Will Be Quick To Explain Why His Marriage Ended

If you’re dating a divorced man in his 50s, he’ll be quick to explain why his marriage ended. He may even be open about what went wrong and how he’s learned from it. But when it comes to dating after divorce, don’t expect him to have all the answers or act like an expert on relationships.

He might not have had much experience with dating since his last divorce—but if he did, then chances are good that he can tell you what he wants from a relationship now as well as give advice on how best to approach things (or avoid them).

If your divorced man has been married before and has children with someone else, then this could also factor into whether or not you want anything serious with him: does being single mean there won’t ever be any chance of having kids together?

A lot depends on each individual situation here—but one thing seems certain: no matter who else lives in their home right now (and whether they still do), their first priority will always remain finding happiness within themselves first before looking outside themselves for happiness elsewhere!

Dating a divorced man in his 50s

2. He Is Likely Different From You In Some Ways

You might be surprised to learn that he’s likely different from you in some ways. He may be more set in his ways, conservative and traditional; or more cautious, independent and practical.

You will also have to adjust to the fact that being married for 20 years doesn’t make him any less vulnerable than someone who has never been married before.

It means he has been hurt by love before—and could be again if you don’t understand what kind of person he is now as opposed to who he was before divorce happened between him and his wife.You’ll have to adjust your expectations for relationships.

3.You Will Have To Adjust Your Expectations For Relationships

The first thing you should do when it comes to dating a divorced man in his 50s is understand that there is no such thing as a perfect relationship.

If you want something more than just sex and companionship, then you’re going to have to be open-minded about what kind of relationship you are looking for, but also realistic about what’s possible with someone who has spent half their life without being married (and probably has had very little time since).

You will also need to be prepared for how much time will pass before he decides where he wants his life headed next—and possibly even if/when he decides at all.

It can take months or years from when one person starts dating another person before deciding if they’re compatible enough for marriage or not; sometimes couples even break up during this process due to differences in opinion about whether or not marriage would work out well long-term.

4. It Is Important Not To Put Too Much Pressure On Yourself Or Him

It is important not to put too much pressure on yourself or him. You can’t change the person you are dating, so don’t try.

Don’t expect him to be perfect and don’t expect your relationship with him to fix all of his issues or problems. You shouldn’t try to change him either because if he does something that makes you angry, it’s natural for us as humans not want someone else’s behavior affecting us negatively in any way shape or form (we know what this feels like).

If there is one thing I learned from my own divorce, it was that people are complex creatures who have their own set of problems they’d rather ignore than deal with them head-on.

Therefore it is essential that both parties involved in a relationship understand each other well before making any promises about being together forever (or even just temporarily).

This means knowing where each other stands emotionally at all times so as not let our emotions get clouded by another person’s actions toward us–and vice versa

5. A Man In His 50s who Is Worthy Of Your Time Knows What He Wants In A Relationship

Dating a divorced man in his 50s

Stability, a strong sense of self, and advancement in his career are things older men can potentially bring to the table more often than a man in his 20s or 30s can, says Sherman. “People often ask whether an older man is more mature than a younger one,” Sherman adds. “It depends upon the individual and their development and history. That said, extra years of life experience do often lead to greater maturity in relationships, and more life wisdom.”

6. kids Out Of The Nest, An Older Man May Have More Time For You

Maybe you’re dating after a divorce, and you’re a single mom who needs to carve out the time for a love life. A man who’s already been married and raised kids has no carpool schedules to contend with, which can mean he’s got more time to plan amazing dates.

According to Lester, if you’re seeing someone who is ten or more years older than you, “he’s likely to have children who are less dependent on him, and have more free time—which can be particularly helpful if your kids are still more dependent.”

7. If He Is Retired And You Are Not, Relating To Each Other Can Be A Challenge

If his working days are behind him and you’re still focused on a job and all the ambitions, woes, and time demands that come with it, you may struggle to connect at the end of the day. “Often relationships are built on similar life experience, and the difference between daily work and retirement can be quite a marked one,” Lester explains.

8. There Might Be An Ex-wife Or Children In His Life

If he is got more than a couple years on you, then he’s likely had a couple more relationships, too. And one of them may have even ended in divorce. Again—not a bad thing.

If your man has been through a marriage that didn’t work out, “they tend to approach the second marriage with more care and wisdom, bringing along lessons they learned about themselves as a partner in the previous relationship,” Carmichael says. (Woot!)

9. Your Sex Drives May Not Be The Same

“Within every couple, regardless of age, there’s always someone who wants more sex or less sex,” Hendrix says. “But that can be even more pronounced with big age differences. An older person has an older body, and older body can tend to have less energy and a different sex drive.”

But this can also be solved by discussing sex openly and whether both of your needs being met. It’s not a deal breaker…just a tough conversation.

Dating a divorced man in his 50s

10. Your Communication Styles Might Be Different

According to Hendrix, older men tend to be good communicators because they have been in serious relationships and they want to get it right this time (remember: emotional maturity).

But you might reach a point of conflict when it comes to the style of communication.”How that filters down into day-to-day connection might have to be negotiated in the relationship,” Hendrix says. Maybe you prefer that he checks on you throughout the day with a “how’s it going” text.

But he’d much rather call you on his lunch break, because texting isn’t his ~generation~. That’s something that the two of you will have to work out. Learning each other’s love languages might be a great place to start.

11. Emotional Reliability 

Finally, it is easier for younger women to relate to older men. Women in their 20s are usually still trying to come to terms with their identity while dealing with the ups and downs of emotional development. They need a strong anchor to keep them centered, and a mature man can provide that emotional stability.

12. He Doesn’t Play Games

He’s already played games in his 20s…and he’s over it.

A young man doesn’t know what he wants, and so he plays those cat-and-mouse games we all hate. An older man, especially one who’s already been married once, knows what he wants. If he’s ready for a long-term relationship, he’ll make it known. You won’t wonder. He’s not out to waste time; he wants to know within a few dates whether you have potential or not.

Now, I’m not saying every older man is ready to settle down again. Plenty want to continue to play the field. But they’ll be more upfront about it if they’re older. At least then you know immediately whether you want to pursue something with him or not, based on whether your goals are aligned.

 13. He’s Financially Stable

An older man is past the early-20s “what am I doing with my life” phase. There’s a good chance he’s midway in his career, and therefore at least somewhat financially stable.

Being financially stable isn’t about making $300k a year. It’s about being smart with his money. Maybe investing it or buying a house. It basically is the opposite of being broke, which is a libido-killer for most women.

It’s nice to date a man who can afford to pay for dinner.

Whose car doesn’t break down in front of your house…

Who has more than one shirt…

Who could afford to take a spontaneous weekend getaway with you…

There is appeal in that, and you can’t always find it with a younger guy who’s still struggling to find his foothold in his career.


It’s important to remember that this is a process of learning and growing, not a race or competition. You don’t need to find someone else right away—and it’s okay if he doesn’t want to date right away either! This is only one step in the long journey toward love, so take your time and enjoy the journey as much as possible.


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