In her recent essay “Sex After 60 in Sag Harbor,” Sex and the City author Candace Bushnell reflects on her dating experiences after 60. She writes, “I needed to stick to the old three-date rule. This is a rule women like me made back in the ’80s.” She makes out with him on their first date but stops there, reminding herself to wait until date three for sex. Later, she finds out from a friend that Ben is a player.
The three-date rule was originally meant to protect women from being rushed into sex. But it still creates pressure—to decide quickly about physical intimacy, often before there’s enough real understanding of the person in front of you. Bushnell treats the rule as something familiar, even comforting. But instead of helping her take her time, it pushes her toward a decision before she has enough to go on. It replaces her own judgment with a timeline—one she follows without questioning whether it still fits. Modern dating after 50 often means questioning the rules you once followed without thinking.
But old rules aren’t the only thing that resurface without thinking.
This piece is part three in a series about Bushnell’s dating experiences after 60. Part one looked at her uncertainty about wanting a relationship. Part two explored how that ambivalence shaped her mindset. This final piece focuses on the habits she repeats—often without noticing—and the consequences that follow.
Bushnell gives another glimpse of how familiar patterns resurface. She describes how “most men love being ‘the subject,’ and they will talk, pretty much only about themselves, sometimes for the entire length of the dinner, and notoriously not ask you one question about you or your life.” Her response? “You do your best. You make an effort. You smile.” She doesn’t speak up, redirect the conversation, or end the date. She doesn’t stand up for herself.
The Risk of Keeping the Peace
Then comes Eddie, a 77-year-old music impresario. He suggests a restaurant. Bushnell writes: “I hate X because bad things happened there with the Real Mr. Big 27 years ago, it’s inconvenient for me, and the food isn’t that good. But I didn’t tell Eddie this. When he insisted on going there, I agreed. Partly because, as in so many situations with heterosexual men, it just feels easier to agree.”
She has clear reasons for not wanting to go—but doesn’t say so. If she had, and he responded poorly, she could have chosen not to meet him at all. Instead, she stays quiet and goes along, avoiding the discomfort of saying no. That choice keeps things smooth on the surface—but it also means she misses the chance to see how he responds when something doesn’t go his way. Because she didn’t say no earlier, she ends up in his car—no longer in full control of where they go or how to leave. By then, it’s harder to speak up, and the stakes of doing so feel higher.
She’s already asked him not to stop at his house: “Please, no, I need to get home. My dogs.” When he does anyway and asks, “Do you want to come in?” she replies, “Do I have a choice?” She doesn’t repeat the no. She doesn’t insist. Her response suggests she feels powerless to stop what’s happening—or that it doesn’t feel safe to push back again. Whether it’s frustration, helplessness, or something closer to fear, she lets the moment pass instead of asserting herself.
With Eddie, she doesn’t assert her no—and ends up inside his house with a man who’s already ignored her no. He gets his marijuana, asks her to spend the night, and she says no. Nothing worse happens. But what if it had?
And it doesn’t end there. The next day, she writes, “When I pulled into my driveway, Eddie pulled in right behind me, but this time in one of those Mercedes sports vehicles. ‘What are you doing here?’ I asked, despite knowing the answer… He had his explanation ready: ‘I was driving by on my way to the dump, and I saw you pull into your driveway.’ I felt a little stalked.”
When Familiar Habits Take Over
Across these stories, one thing keeps happening: she overrides what she’s feeling. With Ben, she follows an old rule instead of checking in with herself. With bad dates, she stays silent while men talk over her. With Eddie, she avoids saying no—and ends up inside a man’s house after he’s already disregarded her no.
If you’ve ever overridden that feeling—the one that tells you this doesn’t feel right, this isn’t someone you want to be around—then you know how easy it is to slip into old habits. But those moments matter. They’re the ones that tell you who someone is, and whether you’re safe with him. And it’s hard to recognize a good partner if you’re not paying attention to what your own reactions are telling you about him.
These habits don’t always feel like decisions. But they are. They shape who you spend time with, how you feel when you leave, and whether you even get the information you need to decide if someone is right for you.
Bushnell tells these stories without apology. But she also doesn’t question the patterns behind them. And that absence of reflection—the ease of slipping into what’s familiar without asking if it still fits—is what makes her dating life so revealing. The stakes change—but the blind spots stay the same.
And these moments of not speaking up can put you in situations where you’re no longer in control of what happens next.
Reinventing your love life after 50 starts with noticing what’s been on autopilot.
What are you still doing out of habit—and does it reflect who you are now?
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It’s not easy to change something you’ve done for decades—even when it’s clearly not working anymore. But you don’t have to figure it out alone. That’s what I help with. Let’s talk. Contact me here.
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