Category - Dating Over 40

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 …

“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 …

There’s a particular kind of loneliness that comes with being told you’re “a catch” while watching everyone else pair off around you. You’ve built a successful career and cultivated meaningful friendships. You have traits that should matter to men — intelligence, depth, presence. Yet when it comes to romantic partnerships, you find yourself perpetually on …

“Personally, I’m into the idea of a 40-something boyfriend, but getting one — and keeping him — would take a lot of energy I’m not sure I have. I have only one friend who has succeeded in this quest, and her boyfriend, a hot surfing instructor named Rodney, still won’t introduce her to his friends …

Candace Bushnell — yes, the creator of Sex and the City — recently wrote about her experience dating later in life. Bushnell’s story doesn’t show us that dating after 60 is hopeless. It shows us what happens when you approach dating without clarity — no matter how iconic you are. You’d think the woman who shaped …

Elena glances in the mirror and tugs at her blouse for the third time. Her lipstick is perfect, but she’s focused on the hollow under her cheekbones she swears wasn’t there a year ago. In twenty minutes, she’ll meet David—a divorced executive she connected with online—for dinner. She’s accomplished, well-read, and genuinely interesting. Yet she …