Jimmy Osgood (Season 5)/Relationships

Virgil 'Static' Hawkins
Initially Jimmy just used Virgil as part of his plan to bring his brother back to life, but over time he became more than just a pawn to him, he became a friend who cared for him and has similar interests as him but to him regardless he still needed to bring his brother back to life so he continued to use him until the day that he attempted a mass shooting and ever since then he came to realize that what he did was wrong regardless of his motives and after he was let out of Juvie, when he was sure that Virgil wouldn't forgive him, he did even before he knew why he did the things that he did and even after he confessed to using him and Richie he still didn't hold it against him and even admired his strategic planning and spying skills, while acknowledging the way he used them was wrong so he offered him the chance to become his personal secret agent that he agreed to and ever since then he helped both Static and Gear solve crime.

Richie 'Gear' Foley
A very similar case to his relationship with Virgil except that Jimmy never knew that Richie is Gear until after the fact due to Richie becoming Gear later on and the additional guilt of accidentally shooting him in the leg.

Nick Connor
Him and Nick have been friends even before meeting Virgil and Richie. They first met when they were infants since their moms were best friends and through most of their lives they were inseparable, well except for a brief period where they weren't that close after Jimmy tried to show Nick his dad's gun, but besides that they are really good friends and Nick, with the help of Kevin Green and Ray Sanderson, at one of time even set up a New Years party for Jimmy for him to catch a break from his secret agent duties in the episode "Childhood Friends".

Kevin Green and Ray Sanderson
Like with Nick, Jimmy has been their friend since they were infants for the same reason and have been mostly inseparable except for a brief period after Jimmy tried to show them his dad's gun but besides that they are good friends.

Johnny Osgood
Him and his brother have always been close and would often hang out with Nick Connor, Kevin Green, and Ray Sanderson together and Jimmy had always blamed himself for his death to the point where he had came up with a plan to bring his brother back to life, but after accidentally shooting Richie in the leg he realized that what he had done was wrong and that his brother would probably hate him for what he had done.

Ebon
Ebon is what you would consider Jimmy's worst enemy as he was the one who tortured than killed his brother even before he was even known as Ebon and thus is the one who caused Jimmy to attempt a mass shooting and Richie to get shot in the first place and even to this day where Jimmy isn't even a villain anymore he considers Ebon to be the worst member of The Meta-Breed.

Rubberband Man
Unlike his brother Jimmy and Rubberband Man have a pretty good relationship as he became Jimmy's mentor in navigating life post-villainy as seen in the episode "Mentor".

Frieda Goren
At first Jimmy had a big crush on Frieda but after he learned that she didn't reciprocate his feelings they agreed to be friends.