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Mackenroth was pre-med at the University of California, Berkeley for the first two years, [3] following in the footsteps of his mother, who was a nurse at Seattle's Harborview Medical Center , but later graduated with a double degree in Fine Arts and Sociology. On October 15, , Mackenroth unveiled a custom-designed wedding gown crafted entirely of condoms as a visual reminder of the importance of safer sex and correct, consistent condom use for San Francisco's Project Inform. His fashion illustrations have also been featured in Nylon , Elle, and in ad campaigns for Tommy Hilfiger and Sushi Clothing. Mackenroth was a competitive swimmer in elementary and high school and continued competing after college [7] at the Masters level. Jack has earned three All-American titles and in the summer of , he set a national record for the breaststroke leg of the 4 x 50 meter relay at the Masters World Championships in Stanford, California.

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