Three years ago, 28-year-old Rylie Middaugh found herself in a “major life change” that brought her across the country to Oregon to begin her photography business. Without a place to stay, she was offered a tiny home to live in, courtesy of her best friend’s stepdad: 75-year-old Tom Ward.
Perhaps even more “unexpected” than this living arrangement was the beautiful friendship that blossomed. One that has left countless online viewers completely invested.
One great example of their dynamic is this video below, which shows text sent from Ward to Middaugh requesting her to bring his hearing aid to work.
This is just one of many endearing convos they’ve shared. Whether it’s encouraging each other to go to the gym, failed attempts at matchmaking, or laughing about everyday mishaps, the exchanges show there’s much more shared between these two than living quarters.
With each new post, people grow more and more captivated by…not to mention a little envious of…this unlikely duo.
“This relationship makes me so happy! 🫶🏻. You’re so good for one another!”
“Wait. This is so wholesome and cute 🥹”
“Does Tom have another bedroom for rent because I have never wanted to be roommates with people so bad 😂😂😂”
“I’m gonna be honest, I’m jealous I don’t have a cool roommate like Tom 😭😭”
Three years in, and Ward and Middaugh have developed their own roommate routines
Middaugh told Upworthy that they try to do dinner together 2-3 nights a week. Tom usually does the cooking, she does the dishes, and they each end the night with chocolate chip cookies, watching one of Ward’s favorite classic movies. A recent watch: It’s a Mad, Mad, Mad, Mad, World!
“Tom usually falls asleep 15 minutes into the movie, so I’m left watching it on my own while he snores beside me,” quipped Middaugh.
The beauty of intergenerational friendships
“The biggest surprise has been how much I’ve come to appreciate the slower, simpler moments,” she added. “After work, we sit around the fire, and Tom tells me stories about his life and those conversations always leave me with a new perspective and tons of laughs.”
During these fireside talks, “age disappears,” Middaugh noted. What persists is their shared love of music as they listen to “everything from The Beach Boys, Neil Young, to Noah Kahan.”
Watching Ward and Middaugh together makes it easy to see why intergenerational friendships resonate with so many people. They create space for wisdom to be shared, fresh outlooks to emerge, and remind us that no matter what chapter of life we’re in, we’re all navigating it for the first time. It’s a dynamic that has found an appreciative audience both on screen and off, with series like Hacks and Only Murders in the Building embracing relationships that bridge generations with warmth, humor, and heart.
The biggest lesson after going viral is one we can all take to the bank
And now, after seeing the overwhelmingly positive response their story has inspired, Middaugh said, “It taught me how much our world is craving real connection.”
Her suggestion to achieve this real connection we all crave? “Slow down” and “appreciate the people right in front of us.”
“Get to know your neighbors, call your grandparents, and have real conversations with people. There are so many incredible people around us if we’re willing to put our phones down long enough to notice them.”
