The person I finally reached out to — and what happened when I did 🐾

It had been over two years. I used the reconnection prompt. She wrote back within the hour. Four ways AI helps me keep the people I love close — all here.

Eight weeks in, and this is the one I wanted most to write.

I’ve been sharing AI tools and systems and frameworks — and all of it has been genuinely useful to me. But this week is different. This week is about the people.

The people we mean to call. The people whose birthdays pass and we send a quick text instead of the real message we meant to write. The people who moved away or whose lives moved on and the space between us grew quietly without anyone deciding to let it.

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The person I finally reached out to

There is someone I went to graduate school with. We were close for years. Life moved us to different cities, different careers, different rhythms. The last time we spoke properly was over two years ago. I thought about her often. I meant to reach out. I didn’t.

Last month I used the reconnection prompt from Sunday’s video. I described her, what she meant to me, what I wanted her to feel when she read the message. AI drafted something. I rewrote it almost entirely — which is exactly what the prompt is designed to help you do. But having that first draft to react to got me past the paralysis of the blank page.

She wrote back within the hour. We have a phone call scheduled for next week.

Two years of silence ended because I spent fifteen minutes with a prompt and ten minutes editing a message.

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The other three ways I use AI for connection

I prepare for important calls now — the same way I prepare for doctor’s appointments. I think through what to ask, what to share, how to open well after a gap. My conversations with the people I love have gotten richer.

I write better letters. AI helps me find the shape of what I’m trying to say. The actual words are mine — but the structure comes from a conversation with AI that helps me get clear on what I actually mean.

And I stay present in the worlds of the people I love — including the younger ones — by asking AI to help me understand what they care about well enough to ask a genuine question. Not to pretend. To actually care, visibly.

🎬 Watch Sunday’s video: All four prompts on screen — the reconnection message, the call preparation, the meaningful letter, and the staying-present prompt.

👉 Sunday video link

⬇️ ALL 4 CONNECTION PROMPTS FROM SUNDAY’S VIDEO ⬇️

📌 Prompt 1 — The Message You've Been Putting Off
"I want to reach out to [describe the person and relationship]. It's been [how long] since we've been in regular contact. Here's what I want them to know or feel: [what you want to convey]. Here's a bit about how I communicate: [your tone/style in a sentence]. Please draft a warm, genuine message that doesn't sound like a template. I'll edit it to sound exactly like me before I send it."

📌 Prompt 2 — Preparing for a Meaningful Call
"I'm about to call / video chat with [person and relationship]. It's been [how long] since we spoke properly. I know this is happening in their life: [what you know]. Here's what I want to share: [your news]. Help me think of: (1) Three questions that would help them feel really heard, (2) One thing I want to make sure I say, (3) How to open the call warmly after a gap."

📌 Prompt 3 — Writing Something Personal That Lasts
"I want to write a meaningful [letter / birthday message / note] to [person and relationship]. Here's what I want to express: [describe the feeling, memory, or love in your own rough words]. Here's something specific and true about this person: [one true specific thing]. Tone: [warm / tender / honest / a little funny]. Please give me a draft that captures what I'm trying to say. I will rewrite it in my own words — I just need help finding the shape of it."

📌 Prompt 4 — Staying Present in Their World
"My [grandchild / adult child / young family member] is really into [something they've mentioned]. I want to understand this well enough to ask one genuine, curious question the next time I talk to them. Please explain [the thing] simply. Then suggest one or two questions I could ask that would make them feel genuinely seen — not like I'm testing them, but like I actually care about what they love."

Here’s what I want to know from you: who is the person you’ve been meaning to reach out to? You don’t have to say who. Just — is there someone? Hit reply and tell me yes or no. And if you want to share who or why, I’m here for that too. 🐾

— Debbie
AI Puppy Playbook