Anne laughs—genuinely–at Richard’s joke.
“You have a great sense of humor,” she says, noticing his left hand has no tan line from a wedding band.
“Life’s too short not to find the funny parts,” Richard replies, his smile reaching his eyes.
He leans forward. “My daughter graduates next month. First in the family to get a master’s degree.”
“That’s wonderful,” Anne says. Grown children. Supportive father. Good relationship with his kids.
“What about you? Any children?” he asks.
“A son in Chicago. We’re close.” Anne sips her wine. “Tell me more about your publishing company.”
“Small but mighty,” Richard says. “We specialize in regional history books. Not getting rich, but I love what I do.”
Passionate about his work. But is publishing stable?
“What about you?” he asks.
“Consulting three days a week now. Easing into semi-retirement.”
Richard nods. “Smart. Life’s for living, not just working.”
Lacks ambition? Or has healthy priorities?
“I have a small place on Lake Champlain,” he says. “Nothing fancy, but the sunsets are spectacular.”
For a moment Anne pictures it: the dock, glass of wine, still air. The kind of evening that makes you forget everything else.
It’s easy to get swept up in that.
“Sounds nice,” Anne says, folding her napkin.
Richard talks about the stars and the quiet. Anne listens. He asks if she likes the outdoors.
“Sometimes. I’ve always lived in the city,” she answers.
Where could this go? Is there enough spark? Why am I not feeling more excited?
It always starts like this—comfortable, calm. But does it last? What don’t I know yet?
She smiles, asks more about his company, and steers the conversation back to safe ground.
The Double-Edged Sword of High Standards in Modern Dating
If you’re a woman over 40 who’s built a successful life, Anne’s story may feel familiar. You know what you want and have worked hard for your peace of mind. You’re not interested in lowering your standards.
That clarity is a strength. It’s part of what built the life you’re proud of. As a psychiatrist, I’ve observed how the same habits that protect you—discernment, high standards, careful evaluation—can also keep you from the very connection you want.
It’s not that your checklist is wrong. The real challenge is subtler: sometimes, the habit of evaluating is less about clarity—and more about protection. Not because you’re “too picky,” but because you know the potential cost of letting a man into your life. You may have a fear of getting hurt.
Anne’s story shows how easily caution can become distance. Personal growth in dating means noticing when self-protection becomes self-sabotage.
The Comfort of Control
There’s a certain comfort in evaluation. It works. It’s familiar. It’s kept you safe in business, in friendships, in life. When you’re faced with the unknown, you analyze, you compare, you measure. It’s second nature.
But dating isn’t a negotiation—or a project to manage. It’s unpredictable. Dating confidence comes from trusting yourself amid uncertainty, not controlling every outcome.
When Healthy Boundaries Turn Into Emotional Distance
Every woman evaluates on a date. That’s normal. The challenge comes when evaluation becomes the main event —when you’re so focused on what’s next, or what could go wrong, that you miss what’s actually happening.
You might notice yourself:
– Asking practical questions instead of sharing what matters to you
– Keeping the conversation on safe topics
– Feeling restless or detached—even when the date seems to go well
– Wondering why excitement rarely follows, even when he “checks the boxes”
Throughout my decades of psychiatric practice, I’ve seen that these aren’t flaws. They’re habits that make sense, especially if you’ve been hurt before. But over time, they can keep you from experiencing the kind of connection you actually want.
The Real Risk
For women over 40, the risk isn’t just “settling.” It’s also the risk of never letting anyone close enough to matter. It’s the risk of keeping your life so well-defended that no one can really get in—not because you’re cold, but because you’re careful. This isn’t about dismissing your hard-earned wisdom but recognizing when it shifts from protective intuition to distance.
Sometimes, the need to stay in control makes it harder to let someone close. Underneath all the careful choices, there might be a quiet worry about getting hurt—even if you don’t call it fear. That caution can shape how much you actually connect with someone, often without you realizing it.
What Gets Missed
When dating becomes a high-pressure evaluation, it loses its spark and genuine connection gets lost. You might miss out on a man who could be a great match—not because he wasn’t right for you, but because the whole experience felt tense and serious. When dating becomes about needing to know the outcome right now, the ease, the curiosity—and the joy—can vanish.
A Different Way to Engage
Taking your time is normal in dating. But when fear influences you to keep conversations light and avoid depth—that’s different from pacing the relationship thoughtfully.
It’s healthy to protect yourself, but if you notice you always keep things on the surface—even when you’d like to connect more—it may be worth asking if fear is getting in the way. Recognizing these patterns is the first step toward changing them.
The Invitation
If dating feels like a puzzle you can’t solve—even though you’re thoughtful, selective, and genuinely open to meeting someone—it may be time for a different approach.
My work is about helping you spot those patterns, so you can feel comfortable, confident, and actually enjoy getting to know a man. This isn’t about lowering your standards—or pretending to be someone you’re not. It’s about finding real ways to feel safe and engaged, so dating becomes something you look forward to—not something you have to figure out alone.
If you’re ready for dating to finally feel different, let’s talk. Contact me here.
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