Hey there! So with the Watch (and most other devices), if you encounter the same prompt, you are welcome and encouraged to re-roll for a new one. You may be traveling with just the watch for your first 5 or 6 prompts but, after a certain point, device discovery would be the only prompt you hadn't yet encountered. That being said, you could complete your whole journey with just the watch but it would be a bit less interesting. I hope that helps and thank you for checking out the game!