When did The Bachelor’s Gabby Windey and Dean Unglert date?

BACHELOR franchise star Dean Unglert described the relationship between him and Gabby Windey on his podcast, Help! I Suck at Dating.

The Bachelor in Paradise alum also revealed on his podcast that he got engaged to  Caelynn Miller-Keyes in October 2022.



When did The Bachelor’s Gabby Windey and Dean Unglert date?
Gabby and Dean are previously dated in college

When did The Bachelor’s Gabby Windey and Dean Unglert date?

Dean Unglert and Gabby Windey are former college sweethearts, according to Heavy.

The two dated for over a year when they were 19 years old, with Dean even referring to her as “the second love of my life.”

Dean once spoke about Windey on his podcast, Help! I Suck at Dating.

“She was, like, one of the main exes. She was my girlfriend from college,” Dean stated.

“Producers called me and were like, ‘Hey, we’re thinking of casting this person—what do you think of her? We know that you dated 10 years ago.’ And I was like, ‘Oh, she’s great. If she gets selected for the show, she’ll either win the show or she’ll be the next Bachelorette.’ And I firmly believe that.”

Who is Dean Unglert?

Dean Unglert was a contestant on the 13th season of The Bachelorette, vying for the heart of Rachel Lindsay.

He was eliminated during the 8th week but later returned to the franchise as a contestant on Bachelor in Paradise two separate times.

Born on April 17, 1991, Unglert is 31 years old.

Dean became well-known in the franchise as a “van-life” guy, living out of his van while he traveled around America.

On season six of Bachelor in Paradise, Dean began to date fellow contestant, Caelynn Miller-Keyes, and the two are currently engaged after being together since 2019.



When did The Bachelor’s Gabby Windey and Dean Unglert date?
Dean Unglert at Universal Studios Hollywood on July 18, 2017, in Universal City, California

What is Dean Unglert’s net worth?

According to Net Worth Spot, Dean Unglert has an estimated net worth of approximately $6.5million, as of October 2022.



When did The Bachelor’s Gabby Windey and Dean Unglert date?

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His main source of wealth is said to be his career as a reality television star.

He also earns income from brand endorsements and sponsorships.


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