The Claude Skill That Plans Every Date Night

The simplified date-planning agent that runs on tools you already have. No API keys, no infrastructure. Browser control handles bookings, WebSearch handles research, three markdown files handle memory. Setup is one interview and one build prompt.

What You'll Learn

• How to teach Claude your relationship (your love languages, her favorites, where you've already been) so every date feels personal, not algorithmic
• The exact intake interview prompt that builds her profile in 15 minutes
• The build prompt that writes the skill file for you
• How to type one command and have Claude plan the date, pick the restaurant, and book the reservation
• Why you do NOT need Resy, OpenTable, Google Places, Eventbrite, OpenWeather, or Google Calendar APIs

The Lie

Every Friday I'd send my fiancée a mysterious text telling her what to wear. By the end of the night I'd surprise her with a restaurant she'd never heard of, in a neighborhood she'd never been to, picked perfectly for the mood she was in that week. She loved it. She started looking forward to every Friday and thought I was finally becoming a thoughtful date planner. I let her think that for almost twelve months. But the credit wasn't mine.

What I actually built: about a year ago I built a Claude skill that planned every single one of our dates. I told it about us, our relationship, our love languages, the cuisines she loves, the neighborhoods we'd already been to, the places she'd mentioned wanting to try. From there I'd type one command on a Friday morning and the entire date was ready. Claude even booked the reservation. The skill never got tired of doing the work humans are bad at doing every week.

What It Looks Like In Practice

Once the skill is installed and the memory files are written, the whole experience collapses to one command. About 3 minutes from prompt to booked reservation.

1. You type: /date this saturday under $200
2. Claude reads everything it knows about your relationship and asks 1-2 questions (budget? vibe she's needed lately?)
3. Claude returns 3 completely different Date Cards. Each has a theme, full timeline, reservation link, parking note, weather, drive playlist, and a "why she'll love this" line tied to her profile
4. You pick one in chat. Or ask Claude to refine ("more low-key" / "add flowers")
5. Claude opens the browser, books the table on Resy or OpenTable, and drops "date night" on her calendar with no details
6. The next morning Claude asks "how'd it go 1-10?" You voice-note. The skill gets smarter for next time

Why the love languages matter: most AI date apps return generic "best Italian restaurants near you" results. The reason this skill picks dates she actually loves is because it knows HER. Her love languages drive whether the date weights gifts vs quality time vs touch vs words of affirmation. A quality-time date is a long dinner with no phones. An acts-of-service date might be Claude pre-arranging everything so she doesn't have to make a single decision all night. Same skill, completely different output depending on what she's needed lately.

The Stack (No API Keys Required)

Four pieces. Everything runs in Claude with tools you almost certainly already have installed.

• WebSearch (built into Claude): for restaurants, ratings, prices, weather, sunset times, drive times
• Firecrawl CLI: for hidden gems on local Reddit threads and niche blogs that WebSearch misses
• Claude-in-Chrome MCP: for browser control to book reservations and drop calendar invites
• Three markdown files in your notes vault: for memory of her profile, your profile, past dates

What you do NOT need: Resy API key, OpenTable API key, Google Places API, Eventbrite API, OpenWeather API, Google Calendar API. All six are replaced by browser control plus WebSearch. The whole point is anyone can install it day one without 8 OAuth flows.

Step 1: The Intake Interview

The skill is only as good as the memory it reads. Paste this prompt into Claude verbatim. It walks you through the questions one at a time and writes all three memory files at the end. Plan on 15 minutes.

I want to build a date-planning skill. Before we build it, interview me to fill in her profile, my profile, and our past-dates log. Ask me the questions one at a time so I can answer each properly. Don't move on until I've answered. When done, write three markdown files:
~/Obsidian/CooperBrain/relationships/fiancee/profile.md
~/Obsidian/CooperBrain/relationships/fiancee/cooper-profile.md
~/Obsidian/CooperBrain/relationships/fiancee/past-dates.md

Questions to ask me, in order:

HER PROFILE
1. What's her name and how do you want to refer to her in memory files?
2. Top 5 cuisines she loves. Top 3 she hates.
3. What kinds of settings does she love? What does she hate?
4. Music genres / artists she actually likes (not just tolerates).
5. Activities she's said 'we should do that' about but you've never gotten around to.
6. Allergies and dietary restrictions.
7. Her top 2 love languages.
8. Introverted or extroverted? What restores her vs drains her?
9. Recent inside jokes or references she keeps bringing up.
10. Anniversaries, her birthday, your engagement date.

YOUR PROFILE
11. Max drive time you're willing to do for a regular date night.
12. Budget bands: weekly date / monthly anchor / special-occasion.
13. Nights of the week that are off-limits.
14. Things YOU don't want to do again.

PAST DATES (last 10)
15. Walk me through the last 10 dates: location, rough cost, theme, her reaction 1-10, anything notable.

Write the three files when done. Confirm to me where you saved them.

Step 2: Build The Skill

After the three memory files exist, paste this second prompt. It writes ~/.claude/skills/date-planner/SKILL.md with the agent loop wired up.

Create a slash-command skill at ~/.claude/skills/date-planner/SKILL.md.

Trigger phrases: '/date', 'plan a date', 'date night ideas'

Behavior:
1. Read all three memory files in ~/Obsidian/CooperBrain/relationships/fiancee/
2. Ask me 1-2 delta questions (budget this week? vibe she needs? Friday or Saturday?)
3. In parallel:
- WebSearch for restaurants + activities matching her taste graph in candidate neighborhoods
- Firecrawl r/[mycity] and r/[mycity]food for hidden gems
- Exclude anything in past-dates.md from the last 90 days
4. Return exactly 3 Date Cards. Each card has:
- Theme (one line)
- Full timeline (6:30pm pickup ... 11pm home)
- Reservation link
- Parking note
- Weather check
- One conversation starter for the car ride
- A 'why she'll love this' line tied to her profile
5. When I pick one, use the Claude-in-Chrome browser tools to:
- Book the reservation on Resy / OpenTable / Tock
- Add a Google Calendar event titled 'date night' with no body content
6. Append the planned date to past-dates.md as Status: planned
7. The morning after the date, prompt me for her 1-10 reaction and update the row in past-dates.md.

Reference the memory files by absolute path. Do not add tools I do not already have.

The Agent Loop

What happens every time you type /date. End-to-end is about 3 minutes from prompt to booked reservation.

1. Delta gather (10 sec): Claude reads memory files, asks 1-2 deltas. Budget? Vibe? Friday or Saturday?
2. Parallel research (30 sec): WebSearch pulls restaurants and activities matching her taste graph. Firecrawl pulls hidden gems from local Reddit. Past-dates.md filters out the last 90 days
3. Three Date Cards (20 sec): Claude builds 3 different cards. Theme line. Full timeline. Reservation link. Parking. Weather. Drive playlist. "Why she'll love this" line tied to her profile
4. You pick one (30 sec): read the 3 cards. Pick one. Or ask Claude to refine (more low-key, add flowers, swap restaurant)
5. Browser books it (45 sec): Claude-in-Chrome opens Resy/OpenTable, books the table, opens Google Calendar, drops "date night" on her cal with no details
6. Post-date capture (next morning, 30 sec): Claude asks "how'd it go 1-10?" You voice-note a few lines. Past-dates.md updates. Next date is smarter

Why past-dates.md is the gold: the skill is only as good as the data it reads. Update past-dates.md every Sunday with her 1-10 reaction. Two months of data and the skill knows what lands and what flops better than you remember it. The reaction column is the most important field by far.

Four Guardrails

Rules that keep the skill working long-term. And keep the relationship working too.

• She knows you use Claude for everything. She just doesn't know it picks the date. That's the framing. If you're not OK with it, swap to "she knows and she loves it" and the skill works the same
• Never auto-book without your approval. The skill returns 3 cards and waits. You pick one. Only then does the browser open Resy. No silent reservations
• Calendar entry stays vague. Always "date night" as the title. No restaurant name. No location. The surprise is the whole point
• Past-dates is the gold. The skill is only as good as past-dates.md. Update it every Sunday. The reaction column does the most work

Build Schedule

Total setup time is about 80 minutes. Spread across 2 days or do it in one sitting.

• Day 1, 20 min: run the intake interview prompt. Answer all 15 questions. Three memory files saved
• Day 1, 1 hour: run the build prompt. SKILL.md is written. Installed
• Day 2: first date. Type "/date this saturday under $200." Pick a card. Watch the browser book it
• Day 7+: post-date capture has run twice. Past-dates.md has real reaction data. The skill is now smarter than your memory at picking dates

One thing to remember: the hardest part of this build is the intake interview. Sit down for 15 minutes and answer all 15 questions seriously. Don't half-answer. The skill is only as good as that intake. Everything downstream is downstream.

Go Deeper

Prefer a printable version? Download the PDF: https://drive.google.com/file/d/14R70XUl2P3o4WGyyyg2ggYQme-jG55oo/view?usp=drivesdk

Want the whole system installed live, with Cooper on the call? Build Your Own AI, the two week sprint runs the first two weeks of August.

Or get a new working tool every Monday inside The AI Operator community on Whop.