The Easiest Way to Win With a Woman (It’s Not What You Think): A Throwback Dating Tip
Let’s face it—the dating world has changed a lot in the past 20+ years.
For men, it used to be as simple as passing a note in class or asking for a number at a party. Now? It’s about sending hundreds of messages on dating apps, often with no response—because let’s be honest, you’re competing with every 6’2” guy flashing his gym selfie.
And with the rise of the #MeToo movement and the shift toward gender equality, many men feel confused about what’s “too forward.” Should you call her? Should you wait for her to initiate? It’s no wonder dating over 40 (and especially dating over 50 websites) can feel like a minefield.
Women aren’t having an easier time, either. We went from being pursued by men who took initiative… to endlessly filtering through dating app profiles, hoping to find someone “normal,” then giving up and deciding it’s easier to just be single.
Why I’m Sharing This With You
I’m Megan Wessels, and yes—I’m single too. I’ve interviewed hundreds of intelligent, relationship-minded women over 40 who are looking for an emotionally available, high-quality man. I’ve listened to their stories, shared their frustrations, and been on enough dates to recognize the common disconnect.
For many men—especially those raised to be the provider and gentleman—it’s a confusing time. You want to do the right thing, but the rules seem to have changed.
That’s why I started this blog (and my newsletter): to clear up the confusion and help good men like you win at modern dating—especially if you're navigating dating over 40 advice and aren't sure where to start.
So, What’s the Easiest Way to Win With a Woman?
👉 Ask her questions. Listen. And respond.
That’s it. It’s deceptively simple—and wildly effective.
I can’t tell you how many dates I’ve been on where I asked all the questions. It doesn’t feel good, and I hear the same thing from other women all the time.
If you’re genuinely interested in a woman, asking her thoughtful questions and holding space for her to answer is one of the most attractive things you can do. It shows that you care, that you’re present, and that you’re emotionally safe.
Why This Works So Well
In the early stages of dating, it’s tempting to talk about yourself—to share what you’ve accomplished, to show that you’re capable and successful. But here’s the truth:
The right woman will be more impressed by how you make her feel than by what you’ve achieved.
Today, women value emotional safety over financial stability or career status. That doesn’t mean success isn’t attractive—it absolutely is! But when you create a space where she feels seen and heard, you instantly stand out from the crowd.
Great Questions to Ask (That She’ll Love Answering)
If you’ve just exchanged numbers, try something like:
“Do you mind if I ask you some fun questions? I think it’s a great way to get to know each other.”
Phone or Text Conversation Starters:
What lights you up? What are you passionate about?
What are some things you still want to experience in life?
What makes you feel fulfilled?
What’s your favorite childhood memory, and why?
What’s something you got away with as a kid that still surprises you?
What was the last book you read?
What’s your favorite podcast, and why?
Did you set any goals for yourself this year? How’s it going?
What are some of your hobbies?
If you could travel anywhere in the world right now, where would you go and why?
First or Second Date Questions:
What are some family traditions you still follow?
Who was your first celebrity crush?
What was one of your childhood obsessions?
What are your thoughts on spirituality, religion, politics?
Have you ever been in love? What did you learn from it?
What’s important to you in a relationship?
What do you visualize for your future?
What things are important to you that money can’t buy?
What’s your proudest moment?
What’s your greatest fear?
What’s been your biggest life challenge—and what did you learn?
What are your priorities in life?
Do you like the pace we’re going at?
Whether you’re dipping your toes back into dating over 50 websites, trying to meet someone special offline, or nurturing a long-term relationship—these questions are your superpower.
The next time you’re with someone you care about, try this approach. Ask. Listen. Respond. You might be surprised how far that takes you.
Happy Dating!
❤️ Megan
