Category - Sex and Dating

“Friday?” “I can’t Friday.” “Saturday?” “Saturday works.” “Great.” They settled on a restaurant. A moment later, Michael said, “What are you doing Friday?” Claire smiled. “I have plans.” “What kind of plans?” “Why do you ask?” “Just curious.” “Are you seeing anyone else?” Claire looked at him, but didn’t answer. Michael waited. “You’re not going …

Laura had been seeing Daniel for almost two months when he called her Sunday evening. They had gone to dinner Friday night. Afterward, they went back to her house and opened a bottle of wine. “Hi,” she said. “Hi. Do you have a minute?” He sounded more serious than usual. “Sure.” “I don’t think we …

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 …