As summer fades and backpacks fill with sharpened pencils and packed lunches, a wave of emotion has swept across Hollywood. For many celebrity parents, the 2023

back-to-school season has been a poignant reminder of just how quickly time flies. From tearful first-day goodbyes to proud milestone celebrations,

stars from all corners of the entertainment world are opening their hearts—and their Instagram feeds—to share this emotional rite of passage.

Jana Kramer: A New Chapter Amid Growing Family

Country singer and One Tree Hill alum Jana Kramer kicked off the school year with an emotional twist. Sharing photos of her children Jolie, 7, and Jace, 4—whom she co-parents with ex-husband Mike Caussin—Kramer revealed a snapshot of a family in transition. While Jolie beamed with excitement, Jace appeared more hesitant, a contrast Kramer captured with humor, writing, “Someone is excited for their first day of school and someone is not 😂. #firstdayofschool.”

The moment was particularly heartfelt as Kramer prepares for another chapter in her own life. She is currently expecting her third child—her first with fiancé Allan Russell—adding even more anticipation and change to this already emotional season.

Ali Fedotowsky: Sentimental Start for a Sentimental Mom

Former Bachelorette star Ali Fedotowsky shared a similarly moving update, sending her daughter Molly off to first grade. “First day of FIRST grade PART TWO!!! HERE WE GO!!! You guys know what a big deal today is to us,” she captioned a carousel of radiant photos. The excitement in the Fedotowsky-Manno household was palpable, even as her younger son Riley, 5, counted down the days to his own return. “HAVE THE BEST 1ST DAY MOLLY!!!!” she added, encapsulating the nervous pride every parent feels.

Savannah Chrisley: A Triumph Over Adversity

Perhaps one of the most touching back-to-school tributes came from Savannah Chrisley, who now has custody of her younger siblings amid their parents Todd and Julie Chrisley’s ongoing legal battles. Savannah celebrated Chloe’s return to 5th grade with deep emotion: “My heart is so happy… all I could do was cry,” she admitted. Having faced a barrage of change, Chloe’s progress symbolized more than just another school year—it was a testament to resilience, growth, and the healing power of love and stability.

Mindy Kaling: Kindergarten Emotions and Fashion Fun

Writer and actress Mindy Kaling marked her daughter Katherine’s first day of kindergarten with a mix of awe and nostalgia. “How is she so big!” Kaling marveled, adding a lighthearted note about her son’s backpack—which she humorously carried. The photo captured Kaling holding her daughter’s hand, a visual metaphor for guiding children through life’s biggest transitions, no matter how emotional they may be.

Jessica Alba: When Milestones Tug the Heartstrings

Actress and entrepreneur Jessica Alba was another parent caught in the emotional whirlwind of kindergarten. As her son Hayes walked off to class, Alba shared a heart-wrenching caption: “My handsome boy 😫💔😢… it’s just still crazy how fast time has flown by.” It’s a sentiment echoed by parents everywhere—the days are long, but the years are heartbreakingly short.

Teen Mom Stars: Generational Reflections

Teen Mom veterans Catelynn Lowell and Tyler Baltierra watched their daughters Novalee and Vaeda take their respective steps into the school world. For Baltierra, the moment struck a deeper chord. “Please stop growing up so fast you guys, your daddy can’t take it!” he confessed. Similarly, Kailyn Lowry showcased all four of her boys headed off to various grades, presenting a snapshot of the beautiful chaos that is large-family parenting.

Jenelle Evans, Gary Shirley, and Jamie Lynn Spears also contributed to the bittersweet montage of celebrity parents, watching their children step into classrooms with new dreams, anxieties, and stories waiting to unfold.

Reality Stars Reflect: Sentiment Behind the Smiles

From Jersey Shore’s Jenni “JWoww” Farley, who posted her children Meilani and Greyson starting school, to Dancing With the Stars pro Lindsay Arnold, who cuddled her daughter Sage before preschool, reality stars were no exception to the universal tug of the back-to-school moment. “And they’re off,” Farley captioned her post, a succinct but emotional summary of what it means to send your babies into the world, one school year at a time.

Khloé Kardashian: A Kardashian-Sized Sendoff

Khloé Kardashian, always one for extravagance, gave daughter True a glamorous kindergarten sendoff complete with a balloon arch and coordinating outfit. Yet beneath the luxury was a mother’s raw honesty: “No, I’m not ok!” she wrote. “Next it will be prom 😫😩.” It’s a feeling every parent, regardless of status, can relate to.

Country Glam and Real-Life Chaos: More Star Moments

Singer Jessie James Decker stood proudly beside daughter Vivianne as she began fourth grade, while Bachelor alum Sean Lowe and wife Catherine Giudici sent their sons Samuel and Isaiah to first grade and kindergarten, respectively.

Actress Jenna Dewan posted a touching snapshot with daughter Everly, whom she shares with ex-husband Channing Tatum, as she set out for a new school year. Meanwhile, April Love Geary captured three of her and Robin Thicke’s children stepping into the academic spotlight—each on a different milestone: Mia entering kindergarten, Lola beginning TK, and little Luca off to preschool. “My babies are no longer babies anymore 😭,” she reflected.