Category - Self-Love

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 …

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, …

They’ve gone out four times. He’s initiated each one, chosen restaurants she wouldn’t have found on her own, paid without hesitation. Between dates, texting is light but steady – a few exchanges every couple of days about articles they’ve read, weekend plans, nothing particularly revealing. On the fourth date, they’re at an Italian place near …

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 …

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 …

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 …

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 …

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: …

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 …

In an ideal world, dating after 40 would be easy.  There would be plenty of great men to meet—emotionally available, genuinely interested, ready for commitment. Men who say what they mean, follow through on plans, and don’t leave you decoding mixed signals like you’re solving a puzzle. You’d navigate dating with confidence, knowing exactly how …