Cheryl Ann Bailey

Cheryl Ann Bailey, 66, of Kentland, Indiana, passed away peacefully on October 28, 2025, leaving behind a legacy of love, laughter, and strength that will forever live in the hearts of those who knew her.

Cheryl shared her life with the late Larry Joseph, her beloved companion and soulmate. Their bond was one of deep devotion and friendship — a love that remained steadfast even beyond his passing.She found joy in the simple pleasures of life — sharing laughter with loved ones, listening to music, watching scary movies, and connecting with family and friends on Facebook. Cheryl especially loved tagging photos of her grandchildren so she could keep their memories close to her heart.Cheryl shared a special bond with her grandchildren, often saying, “I love you to the moon,” and hearing them answer, “and back again.” Her gentle reply, “Forever and ever,” will remain in their hearts as a lasting reminder of her endless love.

Her compassion knew no bounds. Cheryl had a gift for making everyone feel like family. Many of her closest friends she lovingly called her brothers, sisters, children, and grandchildren. To her, family wasn’t defined by blood, but by love, loyalty, and being there for one another.

She was a woman of honesty, strength, and boundless warmth — someone who could fill a room with her laughter and make anyone feel at home. Cheryl’s heart of gold touched countless lives, and her spirit will continue to shine through all who were blessed to know her.

Cheryl is survived by her daughters Christine Joseph, Tracy (Joe) Anderson, and April Leach; her sister Lesa Bailey; niece Katrina (Mark) Showalter; nephew Joshua Bates; her seventeen beloved grandchildren — Christian Leach, Dakota Cochran, Blaze Watt, Logan Watt, Angel (Andrew) Arndt, Carmon (Derek) Erb, Corey Erb, Jasmine (Jorge) Joseph, Dallas (Jessica) Abell, Nadia Spurr, Kevin Spurr, James Bacewic, Miley Gonzalez, Ivy (Noah) Joseph, Jacob Joseph, Kaylee (Tony) Saucedo, and Ethan (Kourtney) Joseph — and her twenty precious great-grandchildren.

She was preceded in death by her mother Pearl Ann Bailey; stepfather Charles Laurinaitis; father John Arthur Bailey; daughter Jennifer Marie Hupp; granddaughter Miley Diane Marie Gonzalez; great-grandson Kolby Mathew Back; great-granddaughter Kiara Starr Spurr; and her longtime companion Larry Joseph.

A service to commemorate Cheryl’s life will be held at Tri-County Bible Church in Rensselaer, Indiana, on November 3, 2025, beginning at 10:30 a.m. (CT). Please join us in celebrating Cheryl’s beautiful life and the love she shared so freely.Her love — “to the moon, and back again, forever and ever” — will remain in the hearts of her family, her friends, and all those she called her own.

In lieu of flowers, memorial donations may be made to Tri-County Bible Church in Cheryl’s memory.

Disposition is entrusted to Comfort Cremations, 674 N. 36th St., Lafayette, IN 47905 | (866) U-R-Loved | www.comfortcremations.net.