Tiffany Conolly biography: 13 things about Miss Cayman Islands Universe 2018 second runner-up

Tiffany LeAnn Conolly is a Caymanian entrepreneur, designer, artist and beauty queen from West Bay, Cayman Islands. She also sings in a small jazz band and in her church youth choir.

Conolly is 8 years younger than her sister Anika Conolly, who was crowned Miss Cayman Islands 2017 on March 25, 2017. Representing the Cayman Islands, Anika was unplaced at Miss Universe 2017 in Las Vegas, Nevada, United States on November 26, 2017.

Tiffany is into mental health, artistic makeup, fashion design, interior design and puppetry. She enjoys painting, modelling, dancing, fundraising and volunteering.

Flag football and softball are among Tiffany’s favorite sports. Here are 13 more things about her:

1. From June 2015 to August 2015, she worked for Cayman National as a credit card clerk,
2. From June 2017 to October 2018, she worked for Cayman Islands Cancer Society as an administrative assistant.
3. On August 11, 2018, she competed against six other finalists at Miss Cayman Islands Universe 2018 at The Westin Grand Cayman Seven Mile Beach Resort and Spa in George Town, Cayman Islands. She was second runner-up to Caitlin Tyson.
4. From September 2019 to November 2019, she was an Alex Panton Foundation administrative coordinator.
5. From October 2019 to January 2020, she was a part-time assistant retail sales manager and a guest relations supervisor at Margaritaville Beach Resort Grand Cayman.
6. In October 2020, she established the Peace of Paradise in the Cayman Islands.
7. In October 2021, she allegedly assaulted her former lover, his father and a police officer and smashed up two cars in West Bay. She was arrested and charged with several counts of assault and damage to property.
8. On August 6, 2022, she competed against seven other candidates at Miss Cayman Islands Universe 2022 at The Westin Grand Cayman Seven Mile Beach Resort and Spa. Sponsored by Island Naturals Cayman, she won the title. Chloe Powery-Doxey was her runner-up.
9. On November 8, 2022, she was officially dethroned as Miss Cayman Islands Universe 2022 and replaced by Powery-Doxey. On November 14, 2022, the case involving the lawsuits filed against her by the men she allegedly attacked in October 2021 was adjourned. On December 5, 2022, the case resumed.
10. On February 9, 2023, Magistrate Philippa McFarlane found her guilty of six criminal counts of assault, damage to property and disorderly conduct.
11. On April 20, 2023, she was supposed to be sentenced but the Summary Court adjourned it due to an incomplete social inquiry report.
12. On June 19, 2023, she visited the official residence of the governor of the Cayman Islands in Seven Mile Beach in Grand Cayman, Cayman Islands. On July 26, 2023, her sentencing was adjourned again to allow for the presentation of further reports.
13. She was 25 years old when she was took to Instagram on August 25, 2023 to share a photo of herself with a caption, “Dirty water doesn’t stop a gardens growth, just as negativity shouldn’t stop yours.”

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