I squinted, staring down the road. “Yeah. I guess. I’d like to think I’m a lot smarter now than I was in college, though.”

“I don’t know about that,” he said before looking down and kicking a stone near his toe. “What’s really bothering you?”

I laughed. “That’s a big question for seven thirty in the morning.”

He looked up at me. “Is it? I’ve never really seen you have any existential angst. Not even after Becks left. You had a couple drunk weekends and then went back to work and never stopped. I mean, is that it? Have you decided that’s all you want?”

The mention of Becky sent a hot poker through my chest. That was happening way too often lately. “I—”

“I keep waiting for you to bring someone over for dinner,” he said, interrupting me. “When I lived in New York, I thought I wasn’t meeting your girlfriends because of proximity. But now that we’ve lived here for—what? Two years?—I’ve only met your platonic fuck buddy, and I’m going to be honest, Jens: I side with Hanna on this one. She’s about as interesting as a spoon.”

This made me laugh incredulously. “You’re one to talk to me about fuck buddies.”

He acknowledged this with a nod. “Okay, that’s fair. I get it. And if that’s what you want to do forever, fine. But then what’s your hang-up about this trip? You can’t have it both ways. You can’t tell me you want to stay unattached and also get neurotic about the Pippa situation.”

“Because I am neurotic, Will,” I said, my voice rising a bit in the damp fog of the morning. “Yesterday, I looked at Ziggs and realized how much she would love to see me have a little summer camp fling, and I was like—sure, why not, I can do this. But there’s something about Pippa that . . .”

“Makes you uncomfortable?” he asked, glancing up at me, eyes steady and knowing.

“Because she’s honest and doesn’t keep shit on the surface?” When I didn’t answer, he continued, “Because she asks you real questions about who you are and what you think? And because you don’t think you’ll be able to evade it for the whole two weeks?”

“Okay, so maybe you’ve put some thought into this.”

“Unfortunately, I have. I mean, I could be back in that giant bed sleeping with my beautiful wife, but instead I’m out here, having Feelings Time with you. So talk to me, Jens. Tell me what’s going on in that head of yours or let me go back and—”

“Okay, okay.” I laughed without humor, turning my face up to the sky. “Jesus, I don’t even know. Somehow she got me talking about Becks last night, and it’s not that I’m still in love with her—the exact opposite, actually—it’s that I fucking hate thinking about it. Why do women like to go there? I don’t even want to go there.”

“This is the extent of your relationships for the past six years,” Will said. “You meet women, go on a date or two, maybe have sex with them, and then don’t call them again. Is that about right?”

I shook my head, but I wasn’t exactly denying what he said.

“You’re a mess, man.” He straightened, brushing any splinters from his shorts. “I bet you even rationalize it by thinking you’re sparing them getting involved with a man who will eventually be inattentive because of his job.”

“Well, yeah,” I said, shrugging. “I haven’t met anyone I can see myself wanting to be with over wanting to work.”

“Can you hear how fucking pathetic that sounds?” he asked, and his laugh softened his words. “When in reality I think you’re just terrified of getting involved and having it end inexplicably again. It’s the same reason you hate talking about Becky. You just don’t understand it. Well I have news for you: None of us understand it. We never did. She hurt everyone. And I get that it’s worse for you—a lot worse—but we all lost her. Now you’re so afraid of trying again you just don’t bother.”

Will shook his head. “This is fear of failure and you’re full of shit.”

Jesus Christ. Why did everything have to come back to Becky?

“I don’t think it’s that deep, Will.” I turned and started walking, slowly enough that he knew I wasn’t simply walking away.

“I’m not saying it’s deep,” he said. “I’m saying it’s obvious. You’re such a cliché. I love you, man, but you are as easy to interpret as a dream about going to school naked.”

This made me laugh. “Okay. So what you’re saying is, I’m a cliché, hung up on being dumped, and overthinking this.”

“In a nutshell.” He smiled over at me. “Did you really get me out of my warm bed to talk about this?”

After another day of wine tasting, and an evening with rich food and a blessedly earlier bedtime, we left just after breakfast on Tuesday. Our second leg of the trip took us from Jamesport to Windham, Connecticut. It was only a couple of hours by car, but having been at the same inn for the last two nights and then packing up to leave made the road trip start to feel real. Four days crashing around various breweries and small wineries, and then we would make our way to Vermont for a quiet week in a cabin.

But before quiet, we had wild. At least that’s how Ziggy pitched the next stop.

It was part of an organized tour of activities, with ten of us in total. Meaning four others would be joining us along the way. Niall gave us a playful lecture—with a lingering look at Pippa—on The Things We Share, and the Things We Don’t.