Winona Ryder romantic relationships get as much attention as her professional career as an actress. In September of 2008, the rumors were spreading that Winona Ryder boyfriend was James Gooding. However, no proof of these rumors ever emerged and they soon finished.

And the current Winona Ryder boyfriend is – James Gooding

In the end of summer of the same year, Winona Ryder was rumored to be involved with Tom Green. They were seen having dinner together which sparked rumors that Tom Green was the newest Winona Ryder boyfriend. Some sources close to the couple even claimed that their relationship was heating up, however there were no proof of these rumors as well.
For one year, from 2007 till 2008, the actress was dating Blake Sennett. When they started their relationship, the public speculated that it might last long, however Winona Ryder and Blake Sennett stayed together for barely one year. The rumors were also going that they were even engaged, but they were never confirmed by neither of the parts.
For a brief period of time in 2006, Winona Ryder boyfriend was considered to be Henry Alex Rubin. They met when Winona Ryder appeared in a mock documentary produced by Henry Alex Rubin. The documentary was about Winona Ryder herself when she was involved in a shoplifting scandal. After the documentary was released, Winona Ryder and Henry Alex Rubin were seen several times in various events, including their appearance on the red carpet. However, soon they finished their relationship.
In 2003, Winona Ryder had an affair with Jay Kay. Jay Kay was quite open about Winona Ryder when asked in an interview by saying that the actress had quite weird sexual desires. In the same year, the actress was rumored to be with Page Hamilton, as well. Winona Ryder boyfriend Page Hamilton is known as a musician from the band “Helmet”. Although they dated for less than one year, they still remained good friends and spoke to each other via phones quite a lot of times after they broke up.
In 1997, Winona Ryder was in a relationship with actor Matt Damon for three years. They were one of the most talked about couples in Hollywood.