Dating a divorced man after 50 can be a wonderful experience. He's been through marriage, knows something about sharing a life with another person, and may have a much clearer idea of what he wants from a partner this time around. There's plenty to look forward to, especially if you're both excited about finding love again.
Of course, dating someone who's been married before comes with a few questions. Is he really over his divorce? How involved is his ex-wife in his life? And what happens if he's sworn off marriage for good, but you'd quite like another wedding someday? Before you get too carried away, here are six things worth knowing about dating a divorced man in your 50s and beyond.
1. Make Sure He's Ready
First things first: is he actually divorced?
It sounds obvious, but there's a considerable difference between a man whose divorce was finalized two years ago and one who's still sorting out the paperwork. Dating someone who's separated can involve ongoing legal proceedings, financial disagreements and the occasional change of heart. Make sure you understand his situation before getting seriously involved.
Then there's his emotional readiness. Some men are eager to date again after divorce, while others need more time to adjust to being single. Don't assume that a man who divorced ten years ago is automatically better prepared than someone whose marriage ended last year.
Ask him what brought him back into the dating world. Does he enjoy meeting new people? Is he looking for a long-term partner? Has he spent enough time on his own to know what he wants next?
His actions will tell you plenty, too. A man who's genuinely interested will make plans, keep in touch and show curiosity about your life. If he repeatedly disappears for days or cancels dates without explanation, there's no need to spend months trying to work out whether he's ready.
2. Learn His History
Nobody reaches their 50s without a little relationship history. If you're dating a divorced man, his previous marriage will naturally come up in conversation sooner or later.
You don't need to turn your first date into an interview about his divorce. There are far more enjoyable things to discuss over dinner! But once you're comfortable together, asking about his marriage and how it ended is perfectly reasonable.
Listen to how he describes his former wife. Does he speak about her respectfully? Can he acknowledge mistakes he made during the marriage? You don't need every detail of their disagreements, but a man who can discuss a difficult experience without turning it into a lengthy attack on his ex is generally easier to have an honest conversation with.
And don't be surprised if his former wife is still part of his life. Divorced couples with children often remain in contact long after the marriage ends. They may attend the same family celebrations, help their adult children or spend time with shared grandchildren.
Being friendly with an ex-wife isn't automatically suspicious. However, if she's calling throughout your dates, making decisions about his personal life or regularly becoming the subject of heated arguments, you'll want to discuss where the boundaries lie.
3. Set Some Boundaries
By 50, most people have established routines, responsibilities and a fairly good idea of how they like to live. Bringing someone new into that life takes a little adjustment, especially when a previous marriage has left financial or family commitments.
Here are three things to talk about as your relationship develops.
• Financial responsibilities: Divorce can leave a man with ongoing financial obligations, including spousal support, shared debts or financial assistance for his children. If he's approaching retirement, these commitments may affect his plans for the years ahead.
There's no need to discuss bank balances on your second date. But before making decisions about living together, buying property or sharing expenses, have an honest conversation about money. Keep your own finances secure while you're getting to know each other, and don't feel pressured to lend money or take responsibility for his existing debts.
• Personal space: Perhaps he's grown used to having the house to himself. He enjoys his Sunday golf games, evenings with friends and the freedom to make plans without consulting anyone. You may be just as attached to your own routine.
There's nothing wrong with maintaining separate interests. In fact, having a life outside your relationship gives you plenty to talk about when you're together. Just make sure you're both willing to set aside time for each other. If every date has to fit around his schedule, that can become frustrating surprisingly quickly.
• Adult children and family: Dating a divorced man with adult children brings another set of relationships into the picture. His children may be delighted that their father has met someone, or they may need time to get used to the idea.
Don't rush introductions or expect to become part of the family immediately. Ask about his children's interests, family traditions and any sensitivities surrounding the divorce. If you eventually meet them, keep things relaxed and allow everyone to get acquainted.
At the same time, remember that you're dating their father. You shouldn't have to get his children's permission every time you want to spend a weekend together.
4. Talk About the Future
Here's a question that can save a lot of disappointment later: does he ever want to get married again?
After going through a divorce, some men are enthusiastic about finding another wife. Others are perfectly happy to enjoy a committed relationship without another marriage certificate.
And there's plenty of middle ground. He might want to live with a partner but keep finances separate. Perhaps he'd prefer to maintain his own home while spending weekends, holidays and special occasions together. Living apart together has become an appealing option for people who enjoy companionship but aren't interested in combining households.
Find out what he has in mind before you become deeply involved.
If you're hoping to remarry, tell him. If you'd rather keep your own home, explain that too. You don't need to start planning the next twenty years over your first cup of coffee, but you should have some idea of whether you're heading in the same direction.
Don't assume he'll change his mind about marriage once he falls in love. He might, of course, but building a relationship around that expectation is a gamble. Take his answers seriously and be equally clear about your own.
5. Watch for Red Flags
A previous divorce doesn't make someone a difficult partner. Still, there are a few behaviours worth watching for when you're dating a divorced man.
• He can't stop talking about his ex: Everyone mentions former partners occasionally, particularly after a long marriage. But if every conversation somehow returns to his ex-wife, their arguments or what she did wrong, he may still have some things to work through. You shouldn't have to spend every date listening to complaints about a marriage you weren't part of.
• He keeps comparing you to her: Maybe his ex-wife cooked a particular meal differently or never enjoyed the same activities you do. An occasional comparison can slip out without much thought. Repeated comments about how you dress, behave or manage your home are another story. Let him know if it bothers you.
• He says one thing and does another: A man who talks enthusiastically about a future together but rarely makes time to see you is sending mixed messages. The same applies if he says he wants a serious relationship but avoids every conversation about commitment. Give him an opportunity to explain, but don't ignore a pattern of broken promises.
• He's looking for someone to run his life: If his former wife handled all the cooking, cleaning, appointments and family responsibilities, he may have some adjusting to do. Helping a partner occasionally is part of a relationship. Becoming his unpaid housekeeper within a few months of dating is quite another matter.
One uncomfortable conversation doesn't mean you should end things immediately. People make mistakes, especially when they're getting used to dating again. See whether he listens when you raise a concern and whether his behaviour improves afterward.
6. Take It Slow
One of the pleasures of dating after 50 is having the experience to recognize what you enjoy in a relationship. You can take your time getting to know someone without feeling that every date needs to lead to an immediate decision about the future.
Start with the things you both enjoy. Talk about favourite books, places you've travelled, hobbies you'd like to try or what a good weekend looks like. Ask about his family, his work and the things he's looking forward to in retirement. Give him a chance to learn about your life as well.
As you become more comfortable together, bring up the bigger questions. What did he learn from his marriage? What would he like to do differently in another relationship? How does he feel about sharing a home or getting married again?
You can also learn plenty from spending time together. Does he treat restaurant staff politely? How does he respond when plans change? Can you disagree about something without turning it into an argument? These everyday moments offer a useful glimpse of what being in a relationship with him could be like.
If you're returning to dating after a long break, online dating can be a good place to start. SilverSingles brings together singles over 50 who are interested in meeting new people. You can browse profiles, exchange private messages and send recorded voice messages to get acquainted before arranging a date.
When you do meet, choose somewhere public where you can talk comfortably. Lunch, a museum visit or a walk through a busy park can all work well. Make your own travel plans, tell someone you trust where you're going and enjoy the opportunity to see how you get along in person.
And don't forget to have fun! Dating a divorced man doesn't have to revolve around his previous marriage. There are new places to explore, stories to share and plenty of opportunities to make memories of your own.
Enjoy Getting to Know Each Other
Dating a divorced man after 50 can lead to a happy, lasting relationship. His marriage may have taught him a great deal about compromise, affection and the kind of partner he wants to be. He may also have a few old habits to shake off. Then again, who doesn't?
Get to know the man in front of you. Be curious about his past, speak openly about your expectations and pay attention to how he treats you. With patience, affection and a little willingness to adapt, you could find yourselves enjoying a wonderful new relationship.
Ready to meet someone new? Join SilverSingles today and start connecting with singles over 50 who are looking for companionship, romance and lasting love.
