Category - Dating Over 40

“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 …

Rachel smoothed her dress for the third time and practiced her smile in the bathroom mirror. She’d read the articles: “Confidence is the sexiest trait.” “Men love self-assured women.” “Fake it till you make it.” So when he asked what she did for work, she gave a polished answer about “exploring new opportunities” instead of …

Maria, a successful woman divorced two years, sits across from yet another pleasant man, nodding as he talks about his hiking trip. It’s her fourth first date this month. He’s nice, but she already knows—there won’t be a second. There’s no spark. No depth. Just another conversation that feels surface-level. As she walks to her …

Emma had an MBA, ran her own business, and gave great advice to her friends about their relationships. But now she was sobbing in her car—humiliated, heartbroken, and confused. Again. Later, she told her sister, “I feel like an idiot. How did I not see it—again?” Her ex-boyfriend had been charming at first. He’d sweep …

Sarah had been on 15 first dates in six months. After a difficult divorce, she wanted to find love again but was scared that she might make another mistake. So she’d spend every date asking detailed questions about the man’s relationship history, career goals, and how he communicates. She thought if she could just gather …

Sarah sighed as she climbed into her car after yet another disappointing date. It had been three years since her divorce, and her love life felt stuck. After tonight’s dinner with Robert, she felt like giving up. “He talked about his job the entire time,” she muttered to herself as she drove home. “And that …

Rebecca smiled as Paul approached her table. They’d matched on a dating app three days earlier. His profile had caught her eye—kind eyes, a warm smile, and a love for hiking, just like hers. Conversation started easily. They laughed over shared tastes in music, swapped Thai food recommendations, and were both reading the same bestseller. …

Let’s be honest: the idea of dating apps might make you want to hurl your phone across the room. And who could blame you? For many women over 40, the thought of creating a profile, choosing flattering photos, and braving awkward first messages sounds more like a chore than a chance at love. But here’s …