Story perspectives
Whitney Cummings Engaged to Skateboarder Chris Cole!
11/5/2025
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Story summary
- Whitney Cummings announced her engagement to skateboarder Chris Cole on November 3 during her podcast.
- Cole proposed during a hike in Topanga Canyon, Los Angeles, using a ring from Cummings' friend Nikki Reed's jewelry line.
- Whitney Cummings, 43, previously ended her engagement to Miles Skinner in 2020, citing wedding-planning overwhelm.
- The couple has maintained a private relationship with limited public appearances.
