24
Jan

When Self-Sufficiency Backfires in Dating Over 40

Lauren met Greg in September through a mutual friend. First date was dinner on a Tuesday. He’s an engineer, she runs her own consulting firm. They talked for three hours. At the end of the night, he kissed her. He called the next day. They made plans for Saturday. By mid-October, they were seeing each …

17
Jan

Why Successful Women Over 40 Stay Single: The Hidden Fear

Emma had been seeing James for a couple months now. Dinner once a week. She liked him – he made her laugh, asked good questions, seemed genuinely interested. He was attractive, successful, the kind of man she’d hoped to meet after her divorce. One Saturday evening at dinner, he brought up the following weekend. There …

10
Jan

“I’m So Tired of This”: The Over 40 Dating Truth Moment

She took the day off, told her assistant she’d be unavailable, and stayed home. Not to rest — she had work to do. It was something she did every year — a hard look at every part of her life, no exceptions. She had a system. Each area got the same scrutiny: career, finances, health, …

13
Dec

Overcoming Dating Struggles: Recognizing Your Turning Point

She’d been invited to a friend’s engagement party. The invitation sat in her inbox for a week. She kept meaning to respond, but didn’t. Every time she opened her email, she saw it — and clicked on something else. She told herself she was just busy. But the truth was, she didn’t want to sit …

22
Nov

What the Holidays Are Like When You’re Single Over 40

This is a feeling many single women over 40 know well, even if they don’t mention it. She arrived at the holiday party just after eight. The host’s living room glowed with candles and string lights, the air thick with wine and perfume and competing conversations. She handed over her bottle of red, accepted a …

15
Nov

What Happens When You Ignore Your Dating Boundaries After 40

They’re on their third date, having dinner. The conversation is good – until he brings up his ex-wife. What starts as a brief mention becomes a long explanation of their marriage, the divorce, what went wrong, how she changed over the years. She listens. She nods. She waits for him to finish. She feels herself …

18
Oct

What’s Blocking Women Over 40 From Finding True Love?

She met him at a fundraiser. During dinner, he turned to her and said, “Does this always go on this long?” She said, “Only when lawyers plan the program.” He laughed. They kept talking through dessert. The next morning, he emailed: “If you’re up for continuing the conversation over real food, I’d like that.” They …

11
Oct

Why Do I Sabotage Relationships? The Hidden Answer

Sarah’s marriage ended years ago. Since then, she’s built a good life — a career she’s proud of, her close friends, and independence. She’s been seeing someone new for a few months. He’s kind, consistent, easy to talk to. Their first conversation lasted three hours. He asks real questions and listens to the answers. It’s …

20
Sep

Make Dating Enjoyable Over 40: The Fun Part Is You

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: …

6
Sep

Breaking Dating Cycles: The Ghost in Every New Beginning

Sarah told herself she’d learned. After James—opinionated, relentless, always needing to win—she promised she’d never date another lawyer. So when she met Michael at a gallery opening, it felt like a relief. An artist. Soft-spoken. Thoughtful. Nothing like the man before. Six months in, the familiar tension crept back. Sarah braced before speaking, defended small …

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