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Orlando Is BACK: Helping His Bestie Chad Transform A Spanish Bungalow Into A… Spanish Bungalow!

I met Chad (in 2018?) at my friend Matthew’s house in Palm Springs. I could immediately tell we had a lot in common. When you’re meeting people by a pool in the desert, you usually end up having dumb conversations about Coachella or something random. So it was refreshing to talk to someone who could not only actively engage in conversation, but also could help lead it and [GASP] ask questions. Chad’s ability to speak in full sentences was especially noteworthy because he is hot. And scientifically speaking, nearly all hot people are physically incapable of asking questions. 

Chad and I became fast friends. We’re both from Northern California. We both went to school on the East Coast and lived in New York. We both have that weird mix of Type A perfectionist and weirdo artist (check out Chad’s pottery on Instagram @panicceramic). We want things to be interesting and unique, BUT ALSO PERFECT AT ALL TIMES. Neither of us is good at relaxing; we’re both perfectionists about our houses. We both love to agonize over super minute details. 

The thing I realize more and more as I age is the importance of older friendships. Meeting people in LA can often feel like you’re being sized up from the get-go. This has been particularly hard for me as someone who, since childhood, has always based my identity on my achievements. Which is fine when I have a book or a TV show coming out, but it often leaves me feeling like a failure if I don’t have some blockbuster “moment” to reveal to a person I’m meeting in an attempt to make them like me and find me worthy.

The kids I went to high school with (I’m looking at you, Caitlin, Sara, and Leigh) know who I am and that I’ve always kind of been the same. They know I’ve always been sincere, hardworking, ethical, and sensitive. They knew I was a TV star before HGTV gave me a TV show. And they know I’m still a star now because we believe that much in each other. When you see the work that goes into building your friends’ lives, you celebrate their accomplishments even when they’re not having a moment. You do this because you know their talent and heart, you’ve seen it for years, you’ve seen it develop. 

Chad came into my life just as I was writing my book and putting together the first season of my HGTV show “Build Me Up.” I’ve had various peaks and valleys in my career, and this was definitely a good peak. I’d worked really hard to get there, and it finally felt like my career was getting to a more stable place. Things were great til 2020, then as we know, things went off the rails. And for me, they remain pretty derailed, but a bit more stable than they were a year or two ago. I won’t get into it as I’ve written extensively about it on my newsletter, but let’s just say it’s been a LONG six years (but things are looking up… finally… I think?).

It’s important to me that Chad knew pre-2020 me. So he sees my potential in its best form rather than viewing me solely through the lens of the challenges of the past six years. Chad is constantly reminding me of who I am and what I can be. He sees my skill and talent when I can’t. And that’s the best thing you can ask for from a friend.

Since 2020, Chad and I have lived parallel yet opposite lives. While I’ve been constantly trying to invent new ways to make money to stay afloat, he’s worked through a few different (very time-consuming) corporate positions. We envy each other’s situations. I envy that he lives a financially stable life where he gets to live in one place and have a routine. He envies that I get to make my living on my own terms, off my creativity. 

Of all the people I know, 2020 was the hardest on Chad. Chad and I had spent New Year’s in San Francisco with our friend Earl, an epidemiologist who spent the entire New Year’s Eve telling us we were all going to die from a virus that was catching on overseas. Mind you, we were in a sweaty dance club, and the last thing we wanted to talk about was a bat disease. Despite our friend scaring us about a virus no one knew about yet, it was a fun New Year and the last semi-normal one for me. 

After the holiday, Chad and I went to Tahoe to spend a few days at his family’s cabin skiing. Like my mother, his mom, Hana, had spent part of her childhood in Japan. So the home was decorated with Japanese art, like the kind I’d grown up with in my house. We spent days skiing, afternoons having cocktails in the cozy, retro 1950s kitchen, and evenings eating hearty, warm meals in the main living/dining space of their log cabin. 

You meet people sometimes and feel like you already know them – they’re that good at engaging and making you feel comfortable. Hana Callaghan is one of those people. An accomplished lawyer, author, and academic, she could have a wildly engaging conversation with a wall. She’s engaging, kind, and protective of anyone who enters her sphere. When I accidentally swapped (the same exact skis with the same exact bindings) after using the restroom at the top of a hill at Pallisades Tahoe, the rental company told me I’d stolen the skis and was liable to pay for them. 

“Would you like me to call them and use my scary lawyer voice to threaten them?” Hana asked me. And she would have done it because she has a fearless effervescence about her that is contagious. Chad’s parents complement each other very well. While his dad has a dry yet laugh-out-loud funny sense of humor, his mom was more outwardly energetic and conversational (meaning: she is really smart and fun to listen to and thus dominates conversations). Those few days at Tahoe were a great little window into Chad, where his personality came from, and which personality traits came from which parent. 

In January 2020, I was mid-season shooting season two of “Build Me Up.” I wasn’t really seeing friends because I didn’t have time between shoot days and doing sponsored content on my days off, but one Saturday morning, I found myself lucky enough to make time to go to the gym. Right as I was about to start my workout, I got a call from Chad.

“My mom died.”

“…What? I’m so sorry…”

I had no words. What can you say? Just a few days before, we’d been in the warmth of Chad’s family cabin, with one of the most engaging women I’ve ever met. How could she be gone?

We’re not really sure what caused Hana’s death (it’s inconclusive whether it was COVID-related or not), but to say this was unexpected is a massive understatement. 

As we all know, 2020 continued to be a pretty terrible year. And on top of all the COVID stuff, Chad lost the most important person in his life.

I bought my house in 2020, and Chad was the only one of my friends who didn’t have COVID when I moved, so he was stuck moving me in. We’d both had home buying on the mind for literal years at this point, but the next year, he started getting more serious about buying and put in 24 offers on houses that were rejected. Finally, in 2022, his 25th offer was accepted, and he was the proud owner of a two-bedroom, one bath, 1000 sq ft Spanish bungalow.

Spanish Bungalow

Chad, having my exact brain when it comes to design, did not see the house as it is when he toured it. He saw what he could make it into. The home itself is charming, but a bit too small to share. So he immediately wanted to add square footage, despite the relatively small amount of space he had to do so. Also, because we’re millennials, we both wondered whether the garage could be converted to an ADU for rental to offset some of the mortgage cost.

My plan for this post was to chat more about what we have in store for this house, but those of you who have been reading me for a while know one thing: I am NOT good at is brevity so today I’d like to stick to the “why?” of it all and keep our plans tucked away for the next juicy post. 

Something I have been trying to be more proactive about in my life is fostering my connections. When you go into crisis mode, the way I have for the past six years, you can retreat. And it takes time and energy to get back into the swing of things with friends and family. A practice I’ve started to remedy relationships that have fallen off is to reach out to people and suggest things we can do together. I asked my mom if she wanted me to come and clean up her garden. I asked my dad to help me cut down trees at my house. Sometimes you just need an activity that can act as the platform through which you can foster a relationship with a friend or family member. 

I wanted to work with Chad on his house because I know how lonely it can be to try and make a ton of design decisions on your own. It’s always better to have someone to bounce ideas off of. I also knew it would be a good excuse to communicate and stay on top of our friendship, in a time when we both felt a little too overwhelmed to prioritize fun.

I think this house is about a lot of things for Chad. Obviously, it’s about the milestone of home ownership and the desire for permanence and home. But it was also just a necessary distraction, a way to focus his energy, after his mom died. Chad is a solver, someone who is very uncomfortable sitting in the unknown. And from the outside, I could tell that his interest, then obsession with buying a house, intensified after Hana passed away. As a friend, I wondered, “Is this just a distraction, something to keep his mind off what’s actually happening?” I wondered if that was just going to postpone some sort of inevitable breakdown later. 

Ultimately, as well as I know my friend, I know he thrives best when you put a task in front of him. He needs engagement. So, of all the things to do upon losing your mother, there are worse things you could do than buy a home with plans to massively overhaul it. A part of my design philosophy for years, and the literal basis for my TV show, was that design is a proactive way to get your brain thinking about the future, how you will care for yourself and your family, and what comes next in life. I do think the house has been a healthy distraction, and I’m glad I’m a part of it.

As far as what we have in store for this house, you’re in for a treat because it’s going to be a major overhaul (I know this because we are actually pretty far into construction already). We will be adding a second floor, turning the garage into an ADU, adding a decent amount of square footage, and honoring the original Spanish style of the home. The plan is to add a bit of a modern vibe to this historic home without negating its original charm. So there will definitely be some noteworthy design moments along with some classic Spanish revival style. 

Follow along, why don’t you, and see what we have in store!

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Lindsey
1 hour ago

ORLANDO AT LAST!!!!!! Bring me alllllll the Orlando all the time, please.

Jill
1 minute ago

If Orlando is here, I’M HERE! Can’t wait to be immersed with Orlando and Chad!

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