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September 19, 2026
Charlottesville, VA

Madison & Rob

leavesleaves

Rob Whelan

&

Madison Gildersleeve-Price

September 19, 2026

Charlottesville, VA
96 days96 d13 hours13 h28 minutes28 min

How we met

11/19/24

Rob and Maddy met at the gym. They had noticed each other before. Maddy was finishing a leg day and Rob came over and said, “Looks like I need to get leg day advice from you.” Maddy said, “Race you up the stairs right now” After flirting and chatting is if they were old friends, they exchanged numbers.

First Date

11/28/24

The day after Thanksgiving, Rob and Maddy met at the Monticello Hiking trail and watched a sunset. Afterwards, not wanting the date to end, they went to the Tea Bazaar to drink tea and play chess. Maddy- The best part about this day is remembering the way it felt to be around Rob. Easy, silly, intriguing.

It’s Official

12/14/24

Rob and Maddy were chatting about exclusivity. Rob said, “So I guess that makes us official” Maddy replied, “Well, you have to ask” Rob paused, thought, and said, “Maddy, will you be my girlfriend?” Maddy responded, “heck yes” It was around this time that Maddy texted her best friend, “I think I met my husband”

Merry Christmas, I love you.

12/24/24

Rob came over after his families Christmas Eve festivities. They were sitting on the couch. Rob looked at Maddy. Maddy’s heart and body got warm, like she was free falling, then Rob said, “I love you”, Maddy replied, “I know; I love you too.”

Engaged

10/18/25

Rob and Maddy had planned to go to Skyline drive to eat dinner and watch a sunset as the leaves were changing. Rob had told Maddy the ring wasn’t ready yet; he didn’t want her to suspect anything. They went on a short hike then headed back to the overlook for the perfect sunset. Rob playfully said “Let’s pretend I’m proposing right now” Turns out, he had the ring. Maddy said “YESSSS”

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