Cassie Randolph Olympian Aly Indiana 2020 Gay and Cassie Randolph Olympian Aly Indiana

Colton Underwood’s Dating History: Aly Raisman, Cassie Randolph and More

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Quite the journey. Before Colton Underwood entered Bachelor Nation, he stepped into the limelight with his first relationship.

In 2016, he made multiple public appearances with Olympian Aly Raisman.The pair were set up by a friend and he fell fast, as chronicled in his 2020 memoir, The First Time: Finding Myself and Looking for Love on Reality TV.“Aly was easy to talk to.

She was open, funny, bright, honest, and inquisitive. She laughed easily and had a smile that I would’ve been happy to simply gaze at for the rest of the night, no further conversation necessary,” the Indiana native wrote, opening up about the romance publicly for the first time. “It was very late when I dropped her back at her hotel, and when I said I’d had a great time,

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