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Dad surprised by his 3 kids with final family carpool before retirement

In honor of their dad’s retirement, a group of siblings teamed up to plan a surprise reminiscent of some of their most treasured childhood memories.

Matt Houlihan, from San Jose, California, came up with an idea to celebrate his dad working 41 years at Saint Francis High School in Mountain View, California, the same school he, his brother and sister attended.

A TikTok trend inspired Matt Houlihan to do something special for his dad, with a special Houlihan family twist, he said.

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“I was scrolling TikTok a week before, [and] I saw a video on a group of grandkids showing up and surprising their grandparents for a sleepover. That kind of got the wheels turning for me, and my dad’s retirement was coming up. And I wanted to do something special for him,” Matt Houlihan told Fox News Digital.

Matthew Houlihan (right) teamed up with siblings Kelsey Houlihan (middle) and Brian Houlihan (back right), and surprised their dad, Tim Houlihan (left), with one last carpool on his final day working as a school teacher. (Matt Houlihan)

Matt Houlihan’s idea required his two older siblings, Brian Houlihan and Kelsey Houlihan, to wake up early with him and show up to their parents’ home. The idea was to take one final carpool with their dad, like they did when they were kids. 

The three siblings decided to go all out by looking back at some of the “rituals” they developed all those years traveling to school in the car with their dad.

“For about eight years, my dad was driving all of us up to high school,” Matt Houlihan shared.

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“And, in that time, obviously, you kind of developed some routines and rituals.”

Houlihan family

Matt Houlihan reflected on all the time he spent in the car with his siblings and dad and thought it would be a great idea to pay homage to those memories. (Matt Houlihan)

After working out the logistics for the surprise, like figuring out how their own kids would get to school, the siblings finally worked together with their mom, Stephanie Houlihan, to make the surprise a success.

The Houlihan children showed up to their family home at 6 a.m. and met their dad with their backpacks, ready to make a trip filled with memories.

They made a playlist, including the songs they’d listen to with their dad while carpooling to school when they were younger, the No. 1 song being “Hey Ya” by Outkast, which was a No.1 hit on the Billboard charts in the early 2000s.

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“At one point, my dad had a CD that was just Outkast’s ‘Hey Ya’ on repeat. So, literally, it was 21 Outkast ‘Hey Ya’ songs burned onto a CD, and we listened for, like, I think, for probably six months. That’s the only thing we listened to in the car,” Matt Houlihan said.

“He always just wants to help everyone who is around him.”

— Matt Houlihan

The next family stop was their favorite bagel shop, House of Bagels, before heading to school and pulling into the same parking spot they had throughout high school.

When the three kids were in school, Tim Houlihan would send them off to class by reciting a quote from the classic film, “The Princess Bride.”

“He would always send us off by saying, ‘Have fun storming the castle,’” Matt Houlihan said, adding that he and his siblings repeated it before their dad walked into his final day of work.

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Tim Houlihan spent 41 years at Saint Francis High School in various roles, starting as a math teacher and bus driver and moving through positions such as office coordinator for the football team and athletic director.

Tim and Stephanie Houlihan with grandkids

Tim Houlihan retired after 41 years at Saint Francis High School and found himself wearing all sorts of hats and stepping into various roles throughout his time at the school. (Matt Houlihan)

He served as dean of students and the gold coach before finally settling into the role of construction management for new projects on the school’s campus.

“We actually got to walk through the last building that he just completed, which was super cool just to see the final kind of crown jewel piece of the campus that he coordinated and helped build,” Matt Houlihan said.

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“And, obviously, then [we] just got to see all the people coming up and saying congratulations to him and seeing all of his at-work relationships like we used to when we were [students] there.”

Houlihan family

The Houlihan siblings captured the video of their dad’s final day of school and shared it on TikTok. (Matt Houlihan)

Matt Houlihan said he and his brother and sister loved celebrating their dad, someone who they always thought of as a “servant leader.”

“He always just wants to help everyone who is around him,” he said, adding that his dad would appreciate his colleagues each year by bringing plates of food to the school security guards who were working the night shift on holidays.

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He has always looked up to both of his parents for the way they care for others. And he saw that in the response of those at the school who said their farewells to his dad on his last day by showing their appreciation for all he did, some even getting emotional saying how much he affected them.

“He would always send us off [to school] by saying, ‘Have fun storming the castle.'”

— Matt Houlihan

Matt Houlihan is now appreciating those special carpools with his father, especially now that he is a parent to two little girls.

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“Being a parent and getting to take your kids to school or taking them to sporting events, you know, those are always the [moments] where so much came out of those conversations in those car drives because, as kids, sometimes you take it for granted that you could spend that time with your parents.”

Houlihan family split

Tim Houlihan drove into retirement with kids by his side, just as they did when they were younger. (Matt Houlihan)

While Tim Houlihan may no longer use “The Princess Bride” quote with his kids, his youngest son Matt is passing that tradition onto his little girls.

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“I always tell them, ‘Have fun storming the castle,’ and then I drop them off at school, so that [the tradition is] carried,” Matt Houlihan said.

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