She asks, “So how do you feel about small talk?”
He says, “I can survive three minutes. Then I need a real question.”
She smiles. “Alright. What’s something you wish more people asked you?”
He thinks. Takes his time. She waits, happy with the question she asked.
Dating after 40 often begins with a list: values, goals, attraction, lifestyle. All important. But none of them tell you what an hour with him feels like. Whether the time passes easily. Whether you find yourself drawn in. Whether you leave lighter than you arrived.
Learning to make dating fun starts with understanding that enjoyment itself has value. It can make the hour worthwhile, even if there isn’t a next time.
Why Fun Matters
You can check all the boxes—shared values, financial stability, relationship readiness—and still find yourself counting the minutes until you can leave. Compatibility on paper doesn’t predict whether you’ll enjoy his company. You’ve probably had that date — his profile looks ideal, his job sounds stable, he even says he wants the same things. And within minutes, you’re already wondering how soon you can leave without being rude.
Most dates won’t lead to relationships. So how do you keep going through encounter after encounter when the vast majority lead nowhere?
Fun. Or learning something new. Or a conversation that makes you see something differently. Without these, dating becomes pure drudgery—a series of failed auditions that drain rather than energize you.
When you approach dates looking for enjoyment rather than just evaluation, you become more curious, more present, more willing to engage. And that makes you more interesting to be around. Fun has its own momentum—when you’re genuinely enjoying yourself, that energy is contagious. Men pick up on this. You don’t have to try so hard — your laughter and curiosity do the work for you.
It often leads to better conversation with a good match. But more importantly, it means each evening has value regardless of whether he calls back. You spent time engaged with another person instead of going through the motions.
Dating isn’t just about finding someone—it’s also about how it feels along the way. That’s why a healthy dating mindset matters. But if you’re not careful, evaluation takes over and crowds out the joy.
The Trap of Evaluation
Evaluation matters — but the trap is acting like you’re just along for the ride, instead of shaping the experience yourself.
You can let an evening pass in polite small talk, never touching the questions you were truly curious about.
The woman in the opening scene didn’t wait to see if he would entertain her – she steered the conversation toward something more engaging. The quality of the evening depends on both of you.
Success can be as simple as having a conversation that made you think, saying what you really wanted to say, or remembering what it feels like to be genuinely curious about someone new. Moments like that help you enjoy the process of dating, instead of measuring it only by outcomes.
If every encounter is judged only by whether it leads to another date, most will feel like failures. But when good conversation has value on its own, dating becomes something you can keep doing without it becoming a chore.
What Fun Actually Looks Like
You’re talking about travel and instead of asking “Where’s your favorite place?” you ask “What’s the worst travel advice you’ve ever received?” He laughs and tells you about the time someone convinced him to pack only sandals for a hiking trip in Scotland. This works because you’ve moved past the predictable questions into a story that shows his personality.
Or maybe you ask, “What’s the silliest thing you believed as a kid?” He admits he thought quicksand would be a daily hazard, and suddenly you’re both laughing at how many cartoons left you braced for nonexistent dangers. These tiny admissions create warmth. That’s dating with no expectations — letting the conversation be enough.
Fun is real laughter, not polite chuckling. It’s when you share something you’re genuinely curious about and he is too. It’s when you discover you both have the same irrational fear or inexplicable pet peeve. These moments feel good because you’re both engaged with what the other person is actually saying.
It’s when you lose track of time because you’re both interested in the conversation.
The Experience Is the Point
Think back to the woman in the opening scene. She wasn’t auditioning for a role or trying to predict the future. She was simply trying to have a good time.
At 40-plus, your time feels even more valuable. You want your evenings to feel enjoyable — and they can. Success isn’t about predicting where tonight might lead — it’s about whether you laughed, noticed something new, or walk away with a story to tell.
Fun makes dating sustainable. Instead of walking away thinking, “Well, that didn’t lead anywhere,” you walk away with something real — a laugh, a story, a moment of connection you didn’t expect. It reminds you that your life is happening right now, not only in a future relationship.
Think of dating like travel. Some trips become lifelong favorites, others are one-time adventures — but each one leaves you with a story, a perspective, or a memory worth keeping. The journey itself matters, not just the destination. A genuine laugh and a story you’ll share with a friend make dating enjoyable.
Women Who Get the Relationships They Want Do This Differently
How can you attract the right partner if you’re not having fun?
When dating feels like work, you miss opportunities to connect.
I help women 40+ enjoy dates and go beyond playfulness—what you reveal, what you notice, how you respond—so you attract the right partner.
Contact me to learn the skills that create lasting attraction and turn promising dates into meaningful relationships.
