Plan a points-funded family holiday and book dinner with ChatGPT agent (partial)

Posted

Jul 26, 2025 by Jitendra (JJ) Jain (@hotelemarketer)

·

Last checked

Oct 16, 2026

·

Method:

How we verify

Evidence: Described by posterThe person describes what happened in words, without screenshots or video.

Outcome

For a points-funded family holiday plan, ChatGPT agent built a decent deck but spent 15 minutes formatting slides; it couldn't book the romantic dinner.

Agent

ChatGPT agent

Strengthened by us to avoid the problem in the source. Not tested by the poster. It doesn't change what happened in the source.

Here's a task I'd like your help with. Read it all the way through before you start.

Goal: Plan a family holiday paid for with my points, and get a dinner reservation sorted.

Check with me first: Which points programme and balance, which dates, and how many travellers?

What I'll give you:
- Points programme(s) and balance ([PROGRAMME], [POINTS])
- Dates and family size
- The restaurant or the kind of dinner I want

Rules:
- Keep the plan simple: a short list or a basic table, not a designed slide deck. Don't spend time on formatting.
- Show flight and hotel options with the points needed and any cash fees.
- For dinner, find the booking link and available times. If it needs a login, card or phone call, stop and give me the link, times and phone number.
- Check that every option has availability on my dates.
- Don't redeem points or pay anything.

Output: A plain plan with flights, hotels, points cost, and the dinner booking link or the details I need to book it.

If anything here is unclear or missing, ask me instead of guessing.

You'll know it worked when: I have a points plan I can redeem and a dinner booking I can confirm in one step.

Plan a family holiday using my points, then book a romantic dinner.

Here's a task I'd like your help with. Read it all the way through before you start.

Goal: Plan a points-funded family holiday as a short deck and secure a dinner reservation.

Quick check first: tell me if anything below is missing or unclear.

Inputs (fill in or confirm):
- Points programme and balance
- Dates and family size
- Restaurant or dinner type

Rules:
- Find award flights and hotels with points prices and cash surcharges.
- Keep the deck to 5 slides with plain formatting; spend no more than 5 minutes on design.
- Try the restaurant's booking provider for the dinner; if it fails, give me the link and phone.
- Show total points and cash.
- Book dinner only after I confirm.
- Compare the points value against paying cash.

What went wrong before, and how to avoid it:
- Last time it spent 15 minutes formatting slides and couldn't book dinner: cap design time and hand over reservations quickly.

Checkpoint: Stop before redeeming points or confirming bookings.

If you get stuck: If the reservation system blocks you, hand over immediately. If a login, CAPTCHA or two-step code appears, stop and ask me to handle it; never guess or store passwords.

Verify before you finish: Check award availability on the airline site.

Output: Deck and dinner status.

Done when: I have a points plan and a dinner booked or ready.

Source

https://x.com/hotelemarketer/status/1949081438076244273