According to FemaleFirst, the actress has a secret relationship with the guitarist from Rilo Kiley, Blake Sennett. They have been dating for quite a few months, and she even came back sooner from her trip in Milan for Fashion Week, to be with Sennett.
A source stated, They’ve been seeing each other for a couple of months now and Winona seems really smitten. They make a real effort to spend time together, and she even dashed back from Milan Fashion Week to be with him when the band were performing a concert in Washington. Things seem to be going really well between them."