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Orlando Wynn

@olandagram

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Come for the heartwarming suburban family photos; stay for the emo Instagram stories after my sports teams lose.

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A very eventful Halloween & Fall 2026 for the Wynn Fam! 🧡💛 by @olandagram

We tired, y’all. Wood Selig and Ricky Rahne failed us as an FBS program. Come soon, January 1st. @odufootball @odusports @odubarstool #ODU #ReignOn by @olandagram

First and likely only #olandapoolbrews at #rountreyliving this summer. Wild. #craftbeer #beer by @olandagram

Russell’s first official first day of school/transfer portal experience. Take care of our boy, Evergreen Elementary. by @olandagram

I had a “Chloe’s starting fourth grade out of respect for Jayden Daniels” joke ready for today, but then she applied makeup and “four perfumes,” so the final joke can be tweaked to reflect it. Side note: I don’t know if I got misty eyed from the fact that she’s growing up or the smell of her fragrances. Happy first day of school, everyone. by @olandagram

Our annual day trip to #Deltaville to see the Norrises caps off the last day of summer (by Chesterfield County Public Schools standards). #olandapoolbrews #craftbeer by @olandagram

Intelligent, polite, upstanding, curious, thoughtful, caring, and a million other superlatives that escape my mind. It’s unimaginable that we’re celebrating your last single-digit birthday, Chloe Rose. Happy NINTH Birthday, and apologies for saying your middle name—I know you hate it. by @olandagram

He did it! Laryngeal cleft surgical repair done ✅ back home with some smiles (and some ‘roid rage), drinking plenty of PediaSure, and hopefully onto more solid food soon. So relieved and thankful for a smooth surgery🙏🏼 now hopefully not too rocky of a recovery process after too🤞🏼 thank you to everyone for your prayers and good vibes and support - we feel it all!! ✨ 💕 we love you Russell Jude Dude by @olandagram

Somehow this is the first #olandapoolbrews of summer 2026. Also it’s the tenth summer of pool brews. #beer #craftbeer by @olandagram

Well that was quick. Started in February and already entering the transfer portal. More Pre-K to come. by @olandagram

More scenes, selfies, and semi-cooperative shots of Russell from yesterday. #orioles by @olandagram

Core memories made at Camden Yards yesterday. #orioles by @olandagram