Travel to Oakfield, specifically the "Rookridge Road" destination. Immediately turn around and run into Rookridge. To your left, there will be 3 guys next to some railroad carts. Kill 2, then move behind the railroad cart until the guy stands still. Then just hit RB and pick the right expressions. I did Kiss My Ass, Growl, Thumbs Up, Dance, and Whistle. I held down A until the green bar stopped moving, then released. Goodluck.
Shoutout to reabo for creating a YouTube video of my solution a while back. Here's the link for reference!