Just One Drink
Speak to Dutch at the camp to begin this mission as Lenny will return to the camp in a state yelling that Micah has been arrested in Strawberry. Before you can attend to matters there, Dutch orders you to take Lenny for a drink in Valentine to calm him down a little. Mount your horse and make your way to the Saloon in Valentine, heading up to the bar to begin the drinking.
Opt for a peaceful resolution to the man that insists on interrupting your conversation before you continue to drink more. The first time you lose sight of Lenny, head over to the nearby table to find Tommy from your earlier brawl and attempt to make amends with him. You’ll have to attempt to talk to him four times until you’re unable to do it anymore, at this point head upstairs to find Lenny.
As the night continues, you’ll lose Lenny a second time, head back downstairs to find him again. Lenny will then go missing for a third and final time, head back into the Saloon (now in first person) and head up the stairs before taking a left and entering room 1A where you’ll interrupt Lenny and his lady friend. Continue to wander around downstairs speaking to the strangers until Lenny comes downstairs and slaps you. Return slaps and eventually you’ll find yourself outside, on the run from the Law. Head down the nearby alley and take a right, opting to jump over the fence to get away. You’ll wake up in a field the next day, sick and hungover as the mission completes.