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Caroline Wakefield

&

Jackson Propst

May 30, 2026

Charlotte, North Carolina
56 days56 d20 hours20 h4 minutes4 min47 seconds47 s

Let's get the facts straight:

Caroline and Jackson met the old-fashioned way - on a popular modern dating app. Caroline was only looking for a date to a law school formal and got a bit more than she bargained for. Jackson was looking for the love of his life, and and now he can't get rid of her. By Caroline's account, their first date lasted a mere 20 minutes (Jackson claims it was 45 minutes) before Jackson had to leave to "do paperwork" (fill out a W-4 form for his first day of work). Somehow in those 20 minutes, Jackson left a good enough impression to get a second date, and the rest is history. Caro and Jack met in Columbia, South Carolina while Caroline was in law school and Jackson began his career as a physical therapist. They both provided support for each other during challenging stretches of life and came out stronger on the other side. Caroline and Jackson often refer to themselves as "America's Worst Couple" because they fear that they may be insufferable. In spite of this, the United States Government did not stop them from getting engaged on June 28, 2024 in Charleston, South Carolina. Jackson planned for pre-dinner cocktails and asked to go on a "walk" to a "special place" (very normal, not suspicious) and Caroline was "so surprised" (knew exactly what was happening) when he got down on one knee. The couple now happily resides in Charlotte, North Carolina and loves to adventure in new cities, enjoy a crispy beer outside, tailgate for South Carolina football, and cozy-up for movie nights with DIY pizza and a bottle of red wine.