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 his office. She’s wearing the navy dress she debated over for twenty minutes. They both order wine, a glass each.
They’re talking about a Supreme Court decision when he says:
“I should probably mention – the next few weeks are going to be brutal for me. We’ve got a major case going to trial and I’m lead counsel.”
She sets down her fork. “Okay. Thanks for the heads up. I won’t expect to hear from you much.”
He stops cutting his chicken. “That’s not what I meant.”
“No?”
“I was just saying I might be slower to respond. Not that I’m disappearing.”
“Right. Of course. Work is work.”
He studies her for a moment. Then he goes back to his plate.
The rest of dinner proceeds normally. He asks about her week, laughs at her story about a disastrous staff meeting, recommends a podcast. But there’s a formality now. He’s pleasant. Engaged, even. But the ease from earlier in the evening doesn’t return.
When the server brings the check, he takes it without looking at it. In the parking lot, he walks her to her car. He kisses her – a real kiss, not perfunctory.
“I’ll call you,” he says.
She drives home replaying the conversation. I won’t expect to hear from you much. Why did she say it like that? It sounded sarcastic. Or defensive. Or like she didn’t care.
Two days later, she texts: “Hope the trial prep isn’t too awful.”
He responds that afternoon: “Thanks. It’s a lot.”
She waits four days. Then: “If you need a break from briefs and depositions, I’m around.”
His reply comes the next morning: “Appreciate it. This sprint should be over in a few weeks.”
She doesn’t text again. A week passes. Then another. Her phone stays quiet.
He told her the trial was coming and that the next few weeks would be intense. Long hours, a lot of pressure. He didn’t say he was going to stop calling; he described what his work life would look like. Her first response was, “I won’t expect to hear from you much.” She skipped past what he’d said and went straight to the conclusion that contact would drop.
Only after that did he add, “I might be slower to respond. Not that I’m disappearing.” That line comes after he hears her treat his news as if he’s already on his way out. It’s a correction. He’s pushing back against the way she has framed him, not making a warm, spontaneous promise.
Before that night, nothing he’d done suggested he would disappear. He was the one asking her out, choosing where they met, paying, and keeping up short, regular texts in between. So “I won’t expect to hear from you much” doesn’t really match how he’d acted so far. It makes more sense as a response learned from men in her past who said they were busy and then stopped making plans. In that moment, she may have felt like she was back in that familiar situation, and she spoke from that feeling rather than from what this man had actually done with her so far.
For her, “I won’t expect to hear from you much” comes straight out of fear. The moment she hears about the trial and the long weeks ahead, she feels that familiar worry: this is where I get left behind. If she tells herself she expects little, she feels a bit less exposed. She’s trying to keep herself safe, even though saying it that way also cools things between them.
When she says it, he takes it as her assuming he’ll disappear. He corrects her: “That’s not what I meant… I might be slower to respond, not disappearing.” She doesn’t ask what he does mean or show any relief; she just says, “Work is work,” and leaves it there.
He feels misjudged. After four dates of effort, she’s already filed him with men who disappoint. He knows he can’t make her happy from there. When she texts, he answers instead of disappearing; sending a quick reply is the easier way out. He never suggests seeing her again.
Was there a chance he was going to disappear once the trial started? Yes. He told her the weeks ahead would be extremely demanding, and he never really said how often he’d be in touch or how seeing each other would work during that time. She may have been picking up how little room there was going to be for her.
But the way she responded all but ensured the outcome she feared. She assumed he would disappear before anything had actually happened. She didn’t ask what he meant by “brutal” or how he saw them staying in touch. She said she wouldn’t expect much, which came across as having already decided how this would go.
So now there’s no way to know what would have happened. Would the trial have consumed him completely and would he have let things fade naturally? Or would he have made an effort to stay connected because he was genuinely interested? Her response at dinner meant the question never got answered.
Giving a man the benefit of the doubt doesn’t mean believing the best. It means waiting to see what he actually does.
Work with Me
Attraction after 40 can change in seconds. You have to read the situation and respond right then—no time to think it through, no chance to get a second opinion. You’re relying entirely on instinct.
You might identify what went wrong after the fact — and even see it clearly. But seeing it afterward doesn’t always change how you respond next time. This kind of choice—how you interpret what a man says, and how you respond in the moment—is exactly what my work is designed to sharpen. Learn more here.
