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Caitlin Flynn

@caitlinsflynnn

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Best time of year in NYC = Honey Deuce szn 🎾 I had such an amazing time at the @usopen this year, especially getting to meet the iconic @patrick.mcenroe! I’m officially a subscriber to his new podcast @macdaddyshow and loving the candid conversations with other sports legends. Hoping he’s right that this is an American man’s year to win 🏆 So happy I got to watch my fav @cocogauff crush it. Sad she’s now out, but at least she can enjoy @cheesecakefactory Also shared my thoughts on all the influencer drama with @simonhernandez for @axios Communicators Thanks @ibm for hosting me and @murphy.janice in the suite. And the hat choice this year is A+
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What dreams are made of ✨ 
Flew to LA last week for @hilaryduff because it was far cheaper than seeing her at MSG and more fun. Thanks so much to @sarahrsaul for hosting @caitlinsflynnn and me

Started the trip at @peacock’s premiere for #TheFiveStarWeekend. A year ago was my first time in Nantucket, and it truly is a magical escape. Excited to binge the rest of the series. The cast is perfection, as was the after-party at @baltaire Made two trips to @erewhon 🍓 First for the Strawberry Glaze smoothie (my favorite). Second to try the $12 Sacred Water. Slide 6 = my review. And loved hanging with @sbhamedy Other highlights = cornbread at @hatchethall, Turkish coffee ice cream at @gingersdivine (h/t @mosheisaacian), lots of @waymo rides, catching up with @neilwaller at @thelighthousecampus and visiting the gorgeous @chief.network clubhouse before it closes

For the concert, I wore an Aperol Spritz tank from @renttherunway in honor of “Adult Size Medium” and loved the @aperolspritzofficial activation 🎶 The outfits (onstage and in the crowd) were just iconic Best for last = very cute pup at a World Cup watch party at @thepenmar 🐶
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Enjoyed a quick weekend getaway on Disney Wish ✨ I broke in my brand new @toystory-themed @away suitcase. We secured the elusive Evie plush dog towel animal, which made my mom’s year. She also finally experienced the AquaMouse water slide We snacked our way through the trip. Highlights include Arendelle’s scallops appetizer (I’m obsessed), churro Mickey waffles and many espresso martinis 🏴‍☠️ We got off at Nassau (time well spent at @senorfrogs) and Castaway Cay. We squeezed in some character meet and greets, including Daisy, Goofy, the BDX droids in Hyperspace Lounge (great addition to the bar) and Spider-Man. And we fully committed to the magic shots featuring Bluey, Frozen, Aladdin and saving the best for last… Hoppers🦎 Dreaming about the next magical experience with @disneycruiseline
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Yesterday was @kerrymflynn’s birthday and I fell asleep while pulling photos from the depths of facebook albums I assumed no longer existed. As I reflect on our literally generational friendship over the last 30(!!) years, I feel very lucky. Not just for knowing and loving Kerry, or for witnessing her journalistic talent bring her to stages we could’ve never dreamed of when we were sitting in a dingy computer lab working on the school newspaper, or for the privilege of being able to live in the best city with your childhood best friend for over a decade, or for writing this insanely long run-on sentence purposefully to annoy her editor brain—but also for ALL of the amazing friends of hers (and that husband) that have immediately become friends of mine. The transitive property has never not applied and I love being part of the package deal. Happy birthday Kerry!! I will always laugh with (and at) you, see the last photo for proof 🎉🎉🎉
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Happy Mother’s Day @flynn_jan!!! As we heard on @disneycruiseline in March, the real treasure is all the memories we’ve made along the way. Cheers to many more ♥️
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2025 is officially in the books! What a year it was, filled with adventures around the world. Just a few of places I went with friends and family: - Savannah - NOLA - Miami - Austin - Sydney - Melbourne - Auckland - Queenstown - Denver - London (x2) - Seattle - Philly - Nantucket - Richmond, VA - Dublin - Orlando - Ft. Lauderdale - Bahamas - Palm Springs - Maui Many Mai Tais were drunk, karaokes sung, dinners cooked, races run, friends hung with, sports viewed, and fun times had. Here’s to more adventures with @kerrymflynn, @falkor_thepup, and everyone awesome.
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2025 was packed! I’m unclear how it was just one year with so much travel, live music, big work moments and some great miles. I also met Josh Hutcherson?! Some highlights… 🦘 dream vacation in New Zealand and Australia — visited LOTR locations, saw wild koalas and kangaroos and enjoyed many breathtaking sights (see my many grid posts) ♥️ family trips to Maui and Nantucket 🏃🏻‍♀️ ran @halflingmarathon in NZ, @nyrr Brooklyn Half and @rundisney Wine + Dine 10K and Half and cheered on friends like the incredible @kit_kenna at the NYC Marathon 🛳️ work + fun on the Disney Destiny 🚀 launched @Axios Media Trends Executive with @sarabfischer ft monthly deep dives, quarterly reports and our first Media Trends Live event ✈️ work trips to @ces, @iab_alm, @sxsw Austin and London, Cannes Lions, @anamarketers in Orlando and MB (LIVE) in Austin and other fun speaking at @advertisingweek NY, @paleycenter, Brands and Culture, ContentCon, The Lead Summit, Tatari’s Forward, Programmatic I/O, @haymakergroup’s Media Summit and @thelighthousecampus 🥂 toasted to newlyweds @davetown.cool in Seattle and @timothybarryheffernan in Cohasset and to @sarahrsaul’s bday in Palm Springs 🍹hosted annual tiki party and first Broadway Cups party 🎶 saw amazing concerts including @themaineband’s 8123 fest in AZ, @grammys ft @chappellroan, @sabrinacarpenter and @charli_xcx, @nbcsnl ft @cher, @badbunnypr and @mileycyrus, @dualipa in Sydney, @beyonce in LA, @kellyclarkson and @geazy in Vegas, @backstreetboys at Sphere, @bostoncalling ft @falloutboy, @whenwewereyoungfest ft @panicatthedisco and @thecab, @neilyoungarchives in Richmond, @jonasbrothers in Boston, @abbavoyage in London, @simpleplan + @bfs_official + @3oh3 in Boston (where we danced onstage), @wethekings + @simpleplan + @avrillavigne at MSG, @kesha + @scissorsisters + @vengaboys at MSG, @ladygaga at MSG, @rauwalejandro at Barclays, @kendricklamar + @sza at MetLife, @hughjackman at Radio City, @boyslikegirls and @alltimelow in Nantucket, @chancetherapper and @jessemcartney and @maydayparade at Pier 17, @teddysphotos, @markronson, @duttypaul + @ashanti, @sukiwaterhouse, @50cent and @kpopdemonhuntersnetflix More in comments…
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Loved celebrating my extraordinary bff @sarahrsaul earlier this month in Palm Springs 🌴 Sarah brought together her family and friends from her different eras of life for her birthday, and it truly transported me back to the magic of The Eras Tour — the power of female friendship, nostalgia and fun The weekend was filled with many special moments including dramatic photo shoots, yard games, playing mermaids, a recreation of one of the best espresso martinis in the world and karaoke (activated the Disney knees) Breaking my toe at this beautiful villa has been the most annoying injury, but I would go through this hell of a healing process again to honor Sarah and to make new memories together 💕
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Feeling wildly grateful. For the ones who showed up, stuck around, called me out, cracked me up until I cried or cheeks hurt, and loved me through every version, phase, and plot twist. Every era did its job and somehow left me with the best life memories. Pulling together all my favorite humans into the desert felt like actual magic. Sound bath zen thanks to @mindbodybadass, fully committing to my @loveisland barbecue fantasy, @partyhostboys feeding me @betchincakes, @dearcaviar dreams, incredible cocktails by @thatsthespirit.ps, a beautiful dinner from @thewrightservice / cake from @inabakesstudio and unhinged amounts of karaoke. Main character energy from start to finish and I regret nothing. This decade already feels grounded, confident, and sparkling in the best possible way. Here’s to living louder, loving harder, and not spiraling over the small stuff. Thanks for being part of Saul’s Eras Tour. Long live 4️⃣0️⃣!🥂✨🪩
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The Fate of Ophelia: Disney Version 🐭🏰✨🧡 Starring @mcwm @hblackington @hsrsmith @kerrymflynn @caitlinsflynnn #DisneyWorld #Epcot #MagicKingdom #Florida #RunDisney
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🖤 They say before you start a war You better know what you’re fighting for 🎰 Loved screaming along and jumping to my favorite pop punk and emo songs last weekend at @whenwewereyoungfest. We saw… @redjumpsuit, @maydayparade x2, @boyslikegirls x2, @wethekings, @thecab, @thestartinglinerock, @themaineband x2, @alltimelow x2, @aof_official, @takingbacksunday, @weezer, @blink182 x2, @panicatthedisco x2, @herleatherjacketofficial, @thesummerset, @destroyboysband, @thestorysofarca, @yellowcard, @simpleplan, @theused, @offspring, @avrillavigne, @loatheasone, @jacksmannequin Bonus: Saw @theclickfive at @hoblasvegas and @thecab at @bbowlvegas — two bands that I loved so much growing up and never thought I’d be able to see again
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OUR PAWS WERE UP!!! 🖤 @ladygaga’s #MayhemBall was spectacular. What a delight seeing Mother right after she was named ARTIST OF THE YEAR at @MTV’s VMAs. Happiest I’ve ever seen Lady Gaga onstage and hope to witness that magic again soon!!!
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