Note: This post contains light spoilers for Chapter 9 of Final Fantasy 7 Remake. We recommend you're at least playing through this chapter before reading this guide.
When you arrive to the Wall Market in Chapter 9, the party is quickly set on a mission to find Tifa by entering the mansion of the reclusive Don Corneo. To accomplish this, Aerith needs to qualify as a candidate in the running to be one of Corneo's many mistresses, so they can easily bypass his heavy security detail. But this isn't a simple process, as you need to the approval of Corneo's closest confidants--one of which is a feller named Chocobo Sam.
Once you start chatting with Chocobo Sam just outside the entrance of the Wall Market, he soon presents you with a coin toss to determine whether or not he'll help Aerith out. You're given three choices: Heads, Tails, or No Deal.
While you might spend the next 10 minutes mulling over what to do, don't waste your time--the coin toss is just one choice in a larger group that impacts how Chapter 9 unfolds. No matter which choice you make, the outcome of the scene will always be the same where you'll guess it wrong. This even applies when you say "No Deal", since Aerith will inevitably decide for you, leading to the same result.
Chocobo Sam is really just messing with you, which lends to the charm of his character--aside from his pitch-perfect Sam Elliot impersonation, of course. You do get a slight hint about him rigging the coin toss beforehand if you talk to the disheartened Johnny, who passes by and rants on about how he should've picked heads.
Your choice in the coin toss is one of a number of decisions that determine which group of side-quests you unlock later in the chapter. In the middle of Chapter 9, you'll receive a slate of odd jobs either from Chocobo Sam or Madam M, depending on your choices. If you choose "heads" or "tails" in the coin toss, that counts toward getting the Chocobo Sam quests.
Other factors are whether you agree with Johnny at the Honeybee Inn or disagree with him (or skip the "Discovery: Vagabond Johnny" moment completely), and whether you choose the luxury or poor man's massage at Madam M's. Agreeing with Johnny and choosing the poor man's massage count toward getting Chocobo Sam's quests. Talking with Johnny's dad at the inn and in front of the Corneo Colosseum also seems to count toward the Chocobo Sam quests. How you describe Tifa to Chocobo Sam may also factor in--saying that she's in great shape likely counts toward Chocobo Sam's quests, while saying that she's a great bookkeeper counts toward Madam M, and saying she's a great fighter is neutral.
Ultimately, this may not be the answer you want to hear about the coin toss choice, but at least, you can breathe easy knowing that your journey through Wall Market isn't completely decided by this one choice. For a full rundown on everything you need to know about the decisions you need to make, read our Chapter 9 choice guide.
For our other guides, be sure to check out our FF7 Remake walkthrough and guides roundup. Otherwise, read our FF7 Remake review for our full thoughts about the game.