- "My girlfriend, the love of my fucking life...Man, I was pulling moves in the joint so this bitch could pay rent. Now, she won't answer the phone."
- ― Dwayne Forge
Playboy X offers Niko some money if he helps out his recently released friend Dwayne. Dwayne wants Niko to recover some money from a guy named Jayvon Simson, who not just ratted out Dwayne and sent him to prison so many years ago, but is also the currently boyfriend of Dwayne's ex-girlfriend, Cherise Glover. Dwayne says that he was sending this money to Cherise while he was in the joint to help her pay her rent, but now that he knows that she was giving the money to Jayvon instead, he wants it back. Niko agrees to help out the melancholic Dwayne saying that Dwayne reminds him of himself.
In order to complete the mission the player must:
- Go to the arcade in Chinatown
- Execute Cherise or let her live
- Chase Jayvon down
- Get Dwayne's money
- Go meet Dwayne at Cluckin' Bell
Head over to the Videogeddon arcade in Chinatown. Niko will spot Cherise and Jayvon together. When Jayvon sees Niko, he fires a Micro-SMG at him but Niko ducks just in time. Jayvon grabs a motorcycle and heads off leaving Niko to quickly deal with Cherise.
The player is given the option to either spare Cherise or kill her. At gunpoint, Cherise begs not to be killed, swearing upon Dwayne's loyalty and that he would want the same, unlike Playboy who would just care for the money. If spared, Niko thinks that Dwayne doesn't need the death of Cherise on top of his other problems, and Cherise will be available for a random encounter later. Her encounter isn't required for achievements or 100% completion. If the player chooses to execute her, Niko will simply shoot her once, thinking that she'd have tried anything to get away.
Get on the nearby motorcycle and chase Jayvon. It is possible to just head due south and cut off Jayvon at South Parkway. If Jayvon happens to fall or is knocked off his bike by any reason, he will pull out the Micro-SMG and shoot back. If Niko runs away from him for a distance, he will hijack/get in the nearest vehicle and chase back Niko. (Might a bug) If Niko outrun from Jayvon for a distance, the player can found him stop and sit still in his vehicle and do nothing until be killed.
For a slightly easier chase, take a car to the mission and run back to it, rather than taking the intended motorcycle. This will allow the player to simply knock Jayvon from his bike and run him over, rather than trying to control the bike and gun at once.
After finished him off and took the money, Niko will automatically phone Dwayne. Meet him at the Cluckin' Bell near Star Junction and give him the money. Dwayne will have a different dialogue depending of which decision the player took, regarding Cherise, if Cherise is spared, Dwayne will say that he's happy she isn't dead due to her being "just an idiot", if Cherise is killed, Dwayne will also be satisfied due to her being "such a bitch".
Liberty Tree Newspaper
"Jayvon Simson's body was one of the many collected by coroners in Algonquin recently. It wasn't a knife or a gun or a rocket launcher that killed this man though... he was killed by video games. Witnesses report a heated argument outside Videogeddon arcade, an establishment where addicts pump quarters into computers to get their fix of horrific violence. The argument was followed by a chase on motorbikes then his grizzly murder. It is no surprise that upset community leaders are pointing to games as the cause of this death: the pattern of altercation, vehicle chase, murder, rebirth and try again is common in video games. Although Mr. Simson was a known drug user and dealer with several convictions, we are certain this case is due to polygons and pixels not parole boards."
- The mission name is a reference to the real-life motorcycle club Ruff Riders.
- This mission is one of several story missions which can be done after completing the main story.
- Cherise's dialogue when she's facing execution is actually hinting the player which one might be the best choice to take in The Holland Play, mentioning that Dwayne will stick to Niko for life and Playboy X will care about nothing but money.
- The post-mission report on Liberty Tree accusing video games as the primary reason of Jayvon's death is likely parodying the various claims of video games instigating real-life violence, with the entire Grand Theft Auto series being a frequent target.
- This mission can be quite similar to No Love Lost as it involves a bike chase and sparing the target's girlfriend, though sparing the girlfriend in this mission is optional.