She left home because she was feeling smothered by her overprotective brothers. They tried to make all of her decisions for her, even choosing who she should marry, the son of the boss and a childhood friend. After some conflict, Sky [redacted] in self-defense. Even though she still loves them, she had to get away to live her life and make her own choices. She still looks back fondly on her time with her dad and brothers.

Skyler has traveled around a bit until she met the first man she fell in love with, Marc Reed. They fell for each other fast and quickly got married when Skyler was only 20 years old. Skyler and Marc got into some trouble selling drugs and were trying to get into a very prominent gang. This along with the fact that they married so young problems started to arise between them. He struggled greatly with communicating his feelings and he needed to work on making himself happy so they mutually agreed to end the relationship and let Skyler move on while he found himself.

This move found her on the west coast, in a city a little north of Los Santos. She met a few people that she came to love, including Mason Brook, and best friend Gracie McCoy. At first she tried to be the good girl and start over but over time she fell back into her old ways. Her younger brother showed up and joined a local MC. This sparked Skyler’s interest and when Mason started to show interest in the MC, Skyler followed suit. One day she was hanging out waiting for friends when a man showed up and forced her into his car. He drove her all the way across town and asked her questions about her life and goals. In the end, he told her that he was from the future and he had seen how the world would end. It was his job to get rid of people that are part of the problem, people who do harm to others in any way. He proceeded to tie her to rollercoaster tracks and then turned on the roller coaster. Skyler survived the attack but sustained very severe damage to her arms and leg. With the trauma of this attack as well as just overall not fitting in in the city, Skyler jumped at the chance to get out when Mason and a few other friends suggested a move. Eventually, things went cold between Skyler and Mason and they split up, deciding to remain friends. Skyler began her life in the new city, getting caught up in some gang activity which led her to meet Jackson Banks (Jax). They had a whirlwind of a relationship, and on Valentines day, Jax proposed to Skyler and they were married later that day. However things went south and Skyler decided it was best for her safety if she was no longer with Jax and on April 24 They both signed the divorce papers and on April 25, they were officially divorced.

April 26, Joe stepped in Jax's place... Joe and Skyler both fell head over heels for each other. Joe helped her deal with her stalker, was with her through her obtaining Skywheels... went to prison with her, Prospected for The Lost with her and then just left her.. just like the rest... After some time, Sky connected with a nomad named Wade but ended things after she realized that he couldn't give her what she ultimately wanted. Recently, her high school boyfriend, Angel Mercer, showed up in Los Santos after searching for her for 10 years.

Skyler used to be naïve and inexperienced which led to her early marriage and she always wants to think the best of everyone. She wants to believe that everyone has the best of intentions, but her experience where she used to live, with drug sales, gang activity, and the attack on her, she is beginning to be very untrusting of people. She still wants to believe the best of people but she is beginning to get a bit paranoid.

Now she lives in Los Santos. She is a member of The Lost MC.

Trivia

• Skyler LOVES the water so much that she has been known to refer to herself as a fish.
• Skyler's nickname for Mason was "Tall, Dark, and Adorable".
• Skyler's favorite moments in LS are now riding around with Jax.
• Skyler loves "chopper" style motorcycles.
• Skyler's Best friend is Gracie McCoy
• Skyler and Jax's relationship started with Skyler telling him she loves his accent and him immediately asking her to be his wife. He actually proposed on Valentines day and they were married less than 24 hours later, By Red.
• Skyler is self proclaimed pothead.
• Angel Mercer was Sky's high school boyfriend who spent 10 years searching for after she left home without a word.

Quotes

• "I get that."
• "I have daddy issues... I don't have daddy..."
• "100%"
• "God, I love him."
• "God Damnit!"
• "Yeah?"
• "When's the last time my life was good?"- Lilith
  "Uhhhhhhh, when I killed your fiance..."-Sky