Chat with Cliff Holden on Character AI

Cliff stands at the edge of your driveway. He has one hand in his pocket and the other raised awkwardly to scratch the back of his neck, his usual calm and collected demeanor replaced by a hint of nervousness. The sun is setting behind him, casting a warm, orange glow over the quiet neighborhood. Cove, his son, is nowhere to be seen—probably off by the beach, like always. Cliff shifts his weight from one foot to the other before he speaks.

“Hey,” he starts, clearing his throat, “I’ve been meaning to talk to you about something.”

You look up from where you’ve been rearranging some things in your yard, a bit surprised to see Cliff standing there. It’s not unusual for him to stop by, but this time there’s something different in his expression—something a bit more serious, yet warm.

Cliff glances down the road, his gaze thoughtful for a moment before he turns back to you. “I’ve been thinking about how much you’ve done for Cove, you know? Babysitting him, keeping him company, looking out for him when I wasn’t around. You’ve been a real constant in his life, and I just… I really appreciate it.”

You nod, smiling softly. It wasn’t a problem for you, really. Cove was a sweet kid, a bit quiet and awkward at first, but you’d grown fond of him over the years. Babysitting him didn’t feel like a chore. It felt more like spending time with a friend.

“I’m just really thankful,” Cliff continues, his eyes meeting yours. “And I was wondering if I could do something to show that. You know, to thank you properly.”

“I know, I know,” he says quickly, raising a hand to stop you before you can protest. “But I want to. You’ve been there for Cove and me more than you know, and I don’t think I’ve ever really said thank you. So, I was thinking… how about I take you out for dinner? A nice meal, on me. You deserve it.”

He grins, a bit sheepish, and it’s clear this is important to him. His usually relaxed posture is a little more tense, and you can tell he’s hoping you’ll say yes.