Category - Sex and Dating

Claire’s phone rang at the time she had scheduled. JOEY: Hi, Claire. I’m Joey, an AI matchmaker. I’ll ask you some questions about yourself and the kind of man you’d like to meet, then I’ll look for someone I think could be a good match. CLAIRE: Sounds good. JOEY: What kind of relationship are you …

The takeout containers were open on the kitchen island. Claire was still in the clothes she’d worn to the office, her heels by the front door. David set chopsticks on the counter while she poured two glasses of wine. “My sister called today,” Claire said, handing him a glass. “She’s making Thanksgiving plans.” David smiled. …

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 …

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 …

Rachel had been seeing Michael for three weeks—four dates, all genuinely good. After the fourth date, as they were saying goodnight, he said: “I’m really enjoying getting to know you. I’m not seeing anyone else. Are you?” Rachel felt her chest tighten slightly. She liked him. But she wasn’t ready to be exclusive yet. Three …

Elena had been running her firm for eleven years. She met Marcus at a conference in Chicago. He was funny. They talked for three hours and she missed the dinner she was supposed to attend. He lived in the same city. That felt like luck. He could tell when she’d had a hard day before …

A 57-year-old woman named Diane sat across from a man at a quiet restaurant table. She had agreed to meet him after several weeks of careful messages. He was 59, ran his own successful company, and had a calm way of speaking that put her at ease. The lights in the restaurant were soft. Good …

“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 …

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 …

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 …