Skipper's friends at the vintage stage were Skooter (1965), Ricky (1965), Living Fluff (1971), and Pose N' Play Tiff (1972).[1]] Skooter and Ricky had their own head molds, and both had freckles. Skooter was available with the same three hair colors as Skipper had, but Ricky was only available with molded red hair, similar to Midge's boyfriend Allan Sherwood.Fluff and Tiff shared a head mold which many collectors think is adorable, with a contagious smile. Most of Skipper's first friends were never seen after the lines they were produced for, but another Skooter doll, called Fun Time Skooter, was produced for the European market. She had auburn hair, a Twist N' Turn waist, and bendable legs. However, she had the head mold of the oldest version of Skipper, not the older Skooter doll, which many collectors found strange.

Skipper's friend for the controveral Growing Up line was the brunette Ginger, made in 1976. However, after this line, Ginger was never seen again. Skipper's first boyfriend, who was named Scott, was created in 1980, and was introduced the year after Super Teen Skipper came on the market. Scott sported puffy brown 1980s style hair.Skipper gained two new friends after Teen Fun Skipper was first introduced. They included the brunette Courtney, made in 1989, and her second boyfriend Kevin, created in 1990.

After Teen Skipper came on the market, her first African American friend appeared. Her name was Nikki, and she was made in 1997. Teen Skipper was originally going to have a third boyfriend named Zach who would have joined her in the "Totally Yo Yo line," but for reasons unknown, he was never produced. Parents speculate that Zach would be too much of a sexual influence on Skipper and children. However, the head Mold for the unreleased Zach Doll was later used for Generation Girl Blaine, the token boy in Barbie's "Generation Girl" Doll line

  • Ricky (1965-1966)
  • Skooter (1965–67)
  • Fluff (1971–72)
  • Tiff (1972–73)
  • Ginger (1976)
  • Scott (boyfriend, 1979)
  • Courtney (1989–2005)
  • Kevin (boyfriend, 1990-1995)
  • Nikki (1997-2005)

these are all skippers friends and boy friends through the years

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