“Just be yourself.” “Be confident.”
But what if you’re not feeling confident? Maybe you’re nervous about dating again, uncertain about what you want, or still finding your footing. It’s hard enough to decide how you want to handle dating situations when you’re not crystal clear about how to reach your goal. It gets even harder when the advice you hear points in opposite directions— making communication in dating over 40 more challenging than it needs to be.
Consider when he asks about your past relationship or what you’re looking for. Instead of helping you prepare, the advice you’ve read can leave you tangled in competing instructions: Share openly, but not too much. Be confident, but don’t brag. Be yourself, but not in ways that might scare him off.
Those contradictions show that dating after 40 isn’t only about finding someone; it’s also where you strengthen the communication skills and confidence you’ll bring into your next relationship.
The Confidence Myth
Dating advice often treats confidence like a light switch: flip it on and you’re ready. In reality, confidence isn’t a performance—it’s something you build by going through situations, making choices, and seeing that you can handle what comes. That process is part of developing healthy communication habits so your conversations with men feel easier and more genuine.
If you haven’t dated in years or your last relationship ended painfully, expecting instant confidence is unrealistic. You’re entering new territory, and it’s normal to feel unsteady.
When he asks about your past relationship, do you give a polished version, keep it light, or share more? These moments aren’t tests you pass or fail—they’re small choices that shape how you feel with each man.
The Authenticity Puzzle
“Be yourself” sounds simple — but authenticity in dating after 40 can feel less clear when you’re across from someone wondering which “self” that means. You have different sides: the hopeful, the skeptical, the decisive, the unsure.
You want someone who responds to who you truly are, not to a role you’ve learned to play. But mixed messages can make you doubt how much to share. Should you talk about the promotion you’re proud of, or hold back so you don’t intimidate him?
Advice often tells you to be genuine and open, but also to avoid oversharing or appearing too eager. The gap between those two instructions can leave you second-guessing your most natural responses.
The “What Are You Looking For?” Dilemma
Another common contradiction — and one of the real over 40 dating challenges — is hearing “Know what you want” versus “Don’t be too focused on outcomes.” If he asks what you’re looking for, the calculation begins: say you want something serious and risk sounding as if you’re interviewing him; say you’re keeping it casual and risk attracting men who don’t want the same future you do.
Your real answer might be:
“I’m looking for someone who gets my sense of humor and doesn’t mind that I talk to my plants.”
“I’d like a partner to travel with and build a life with.”
The question isn’t which is “correct,” but which fits the moment — whether that means sharing openly, holding back, or keeping it light.
When He Asks About Your Past
You could say, “We grew in different directions,” “It ran its course,” or, “That’s a story for later.” One expert says to share lessons learned, another to keep it private, another to use humor. The better guide is how the question lands with you: does it feel curious and caring, or invasive?
Finding Your Own Words
Contradictory advice can make you second-guess responses that would otherwise feel natural. Sometimes you know exactly what you want to say. Other times you hesitate, unsure how much to share. Both are normal — and both are part of building the skills you’ll need for the relationships ahead.
On one date, you might keep your answer light and watch the conversation glide past. On another, you might share more openly and notice how that changes the dynamic. Neither choice is wrong — both teach you something about how you want to handle similar moments next time.
It’s rarely about finding a perfect universal script. More often, it’s about noticing which responses feel right for you in that moment. Over time, those moments of choosing your words start to shape not just what you say, but how you communicate with men
Moving Forward
Mixed messages can make even simple conversations feel complicated. Knowing what to do when dating experts disagree can help you trust your own voice instead of getting lost in conflicting opinions. Each time you decide how to respond, you’re practicing how to communicate more effectively with men — and building the skills and confidence that will serve you not only in dating, but in a future relationship.
That doesn’t happen instantly. It grows through trial and error, and through noticing which conversations leave you feeling more at ease and which ones challenge you. Some choices will feel right, others less so, but all of them help you get better at expressing yourself in a way that works for you.
Each time you do that, you’re setting aside the noise of conflicting advice and relying a little more on your own judgment. And that progress matters — because it moves you toward the kind of relationship you want, whether or not it’s with this man.
Accelerating Your Path to the Right Relationship
How you handle dating now helps prepare you for the relationship you want next.
Figuring it out alone can take years — and cost you chances with men who might have been right for you. I work with women after 40 to speed up that learning curve, so when the right man shows up, they know it — and know what to do next.
Let’s talk about how to fast-track that process — you can reach me here.
Dating after 40? Your journey so far is your greatest asset.
The experiences that might feel like baggage? They’re actually your secret weapons for finding lasting love.
Discover why in my free guide “Dating Over 40? Know Your 7 Secret Advantages.”
