Dating After 60: What to Ask a Man Who Never Married

You’re enjoying dinner with a man you’d like to see again. Then he says he’s never been married, and you start wondering what you missed. At his age, shouldn’t he have made it down the aisle at least once?

If you’ve been divorced, his history can feel harder to explain than your own. You know what it takes to share a life with someone. Has he ever tried?

Give him a chance to answer. A previous wedding won’t tell you whether a man can listen when you’re upset or make room for you in his week. Those things take time to learn, whichever box he checked on his dating profile.

Let Him Tell You About Someone He Loved

Here’s a question that leaves room for his story: “I’d love to hear about a romantic relationship that felt important to you.”

He may have spent years with someone without marrying. Perhaps he wanted children and she didn’t, or he never wanted a marriage license. If you’re dating after 60, ask whether he’d make the same choice about marriage today. Hear how he sees those choices now.

Listen to how he describes his former partner. Does he remember what he appreciated about her? Can he explain why they parted without making her responsible for everything?

You don’t have to collect his entire dating history over dessert. If he mentions a painful breakup, let him choose how much to share. You can learn more as you get to know each other.

In my conversation with Second Act TV host Silke, we talk about why a never-married person can draw more suspicion than someone who’s divorced, and about the good stories behind those single years. Listen to the conversation before your next date if you want another perspective.

Ask What He’s Looking for Today

“What are you hoping to find by dating?” is a fair question. Please don’t avoid it because you like him.

He might want a lasting relationship without a wedding. Would that make you happy? If you want to marry, say so before you start imagining that he’ll change his mind for you.

Talk about exclusivity, too. Try: “I’m interested in dating one person once we know we want to keep seeing each other. Is that something you’d want?”

If his answer is that he only wants something casual, believe him. You can think he’s great and still decide to stop seeing him.

As the relationship develops, ask whether he’d want to live together or keep separate homes. My questions about commitment give you other ways to begin that conversation. Share your own answer, too, so he isn’t sitting through an interview.

The 3-Date Strategy in my free webinar, The Three Secrets to Finding and Maintaining Healthy Love, gives those early dates some structure for learning about compatibility.

See How He Handles an Uncomfortable Moment

Ask him what he’s learned about himself in relationships. “I used to shut down when I was upset” gives you something to discuss. “Every woman I’ve dated was impossible” leaves you with a different concern.

His answer matters. You’ll also need to see what happens between you.

Suppose you disagree about where to meet. Can he hear your suggestion, or does he stop replying until you agree to his plan? If he says he’s become a better listener, notice whether he lets you finish a sentence.

Being rusty about arranging a date is understandable. Disappearing for days whenever he’s annoyed is something you get to object to. You don’t owe him endless patience because he’s had less relationship experience than you.

In Conclusion…

A marriage certificate doesn’t prove someone is more capable than a person who never married, or who never had a long-term relationship. I want my clients to drop the shame about their single years, and to hear someone else’s story with that same openness.

When you’re dating someone who has never been married, the biggest misconception is that you know anything about him before you’ve asked. Find out what he’s learned, how he talks about his relationship experience, and what he’s committed to now.

Check out this link if you struggle with eliciting or practicing honesty in dating. This includes feeling free to ask the questions you need to ask and share your own reasons for being single.

Your guess about him might be right. I’d put the odds at about 1 in 50. That’s no substitute for the truth gleaned from an actual dialogue with another human being, which in the age of AI, I really hope we keep practicing.

Also read, Living Apart Together: Is It the Right Choice for You?

Let’s Have a Conversation:

What could make you suspicious about a man you’re seeing on a date? Would someone who has never married seem different than someone who is divorced?