A Philosophy of Life and Roller Skating With YouTube's Favorite Instructor

A Philosophy of Life and Roller Skating With YouTube's Favorite Instructor

Deborah Monterossa says she had no idea what she was doing when she posted her first rollerskating tutorial to YouTube. Her channel, Dirty School of Skate, hosts a bevy of skating tutorials all starring a cheerful Monterossa, a.k.a. Dirty Deborah Harry, encouraging viewers that with enough practice and a flat surface they can do what she is doing and then some. Each video focuses on a different skill set but also seems to capture the jubilation that comes from skating—and two years and 122,000 subscribers later, she seems to be getting the hang of things.

I first discovered Monterossa in April when I started picking up an interest in rollerskating as a quarantine hobby. Between the first week of April, when I started watching her channel, and mid-May, when I laced up my own wheels for the first time, I’d developed almost an apostle-like admiration for Harry, who felt like the only person who truly understood this strange, obsessive feeling I had about an activity I’d not attempted since I was seven.

Her instruction was clear and concise; she talked slowly and directly about every skate mechanic no matter the level of difficulty. From stopping in the safest manner to jumping in your skates (I still can’t nail this but almost there), Harry treated every part of skating as if it was the most worthy use of her time and spoke to her invisible online students as if they were paying for private lessons. There was something else about Harry’s videos and teaching style that felt extremely welcoming that I couldn’t quite put my finger on—until we spoke for the first time and I tried my best to not fan-girl like an absolute loser.

Even with the money and time I had invested into skating, I couldn’t figure out what it was about the activity that kept me coming back. I’m not that good at it, I don’t have friends who skate and live close to me so I mostly do it alone, and I literally almost broke my ass trying to go down a ramp at a skate park.

But Harry’s overall skating philosophy, which she explained in a phone call with Jezebel, somehow made the whole world and the world of roller skating make more sense and seem more wonderous. The conversation that follows has been condensed and edited for clarity.

Dirty Deborah Harry: So what’s going on, have you been skating?

Jezebel: I have yes, I picked it up in May and about 95 percent of my lessons were strictly from Dirty School of Skate.

I’m so glad you’re watching the videos, they must be working if you’re still skating.

They are! I mean I’m not great but—

You know, it’s funny because very often I get people telling me like, well, I’m not any good and if I just say my God, skating is a lifelong journey. You know, my uncle still skates every day and he’s 89 years old. Definitely, something that once you start it can be a passion that will follow you for the rest of your life. So with that in mind, don’t ever think, oh my God, you know, I have to be good right now. Just enjoy any progression at all.

So I know from watching your videos, your family has owned a roller rink for a while, right, and because of that, you’ve been skating since childhood basically?

I’m third generation into [rollerskating] on both sides of my family. My grandparents on both sides of my family were skaters and skating teachers and my parents both were skaters and skating teachers. With that, my dad’s entire extended family were skaters and teachers. So it’s really a family business, and we have been skating since I was about three. My family opened up the Fountain Valley Skating Center in Southern California in 1976. When we opened it up, it was like the typical family business where it was all hands on deck, everyone worked there. My dad had a full-time job elsewhere and spent his days off mounting plates on skates. So it was a fantastic way to grow up because I was where I wanted to be, which was, you know, at the roller rink.

I would beg my mom to just let me skate session at the rink. Session is where they let the general public in and they blast the music and you have a good time. I used to say I was the only 10-year-old with a nightlife.

When you first laced up was it something you naturally fell into or did your parents have to push for you to stick with it?

I was three when I first started skating and it was totally in both me and my sister. Now, my brother would come [practice at the rink] occasionally, but mostly my mom didn’t want him to come because he was a pain in the ass. He would come to the rink and he wouldn’t want to come to artistic practice, he would just spend his time running into kids and tackling them on his skates.

So you’ve been going to Fountain Valley for years, it’s a huge part of your family’s history. What was it like when covid started becoming more prevalent and the realization hit that the rink would have to close?

I came to that realization in a bar I was in the night before St. Patty’s Day, like you could feel it in the air and just listening to everything. I had to work at the rink one Monday night and during the day we weren’t sure what to do. There was a session starting at eight and we decided to still do it thinking it would be the last one. This is back when we thought we’d only have to be closed for two weeks. And we were devastated by two weeks because in small family businesses, you never close. You know, we can never close, we close one week out of the year, every year, to refinish the floor. Beyond that, we never close. So for us to say, oh, we’re going to close for two weeks is huge. So then it was like, oh, it’s going to be a month. And then it just kept getting longer and longer and longer.

Have you guys opened at all since March? My local rink was open for about a month in the summer at capped capacity before they had to close again because of restrictions.

No, we have had other rinks in the Southern California area that have opened and closed right away because, you know, there’s nothing specific for skating rinks. So you kind of sit there and think, are we a gym? Are we kind of an amusement park? Are we a restaurant, what are we? So we’re being super conservative.

I miss the sessions and seeing all the people so happy on the floor. I miss that social interaction. But we’re gonna get there, you know, I got my fingers crossed for this vaccine.

So how did you go from an artistic figure skater to derby player, to making videos on YouTube?

I started making the YouTube videos two years ago. I’ve wanted to do it for a very long time, but it always for me, takes people really urging me to do something before I’m just like yeah, I’ll do it. At some point even my mom was saying, you should do that YouTube thing. So I called up my nephew who hardly spoke any English, but my husband speaks Spanish, and I said tell Xavier to buy some software, learn how to edit videos because when I get back [from Spain] we’re going to make videos.

And he did it, he spent all his time calling his friend in El Salvador trying to figure out how to do all these different programs. So I said, all right, let’s just go out today, and let’s just film the video and just see how it goes. But I had been teaching basically skating full time since 2010. I got back into skating heavily back in 2006 through roller derby. And I had seen through roller derby that, wow, there is a massive need for people to learn how to skate properly so that they can excel in skating and so that they do not get injured.

Do you remember what the reception was to your first few videos?

It was hilarious because I did not know anything about YouTube, right, so I didn’t know it was hard to get— I swear to God, it’s not me bragging—I didn’t know it was hard to get subscribers and I got like 100 subscribers in a day which apparently is a milestone.

I had no clue. I mean, it was lucky I even got it up on YouTube. I sent out a text to some friends like, hey, do me a solid and watch this video, hoping at least one person would watch it. Well, a week later, I had like a thousand subscribers and I was getting all these messages and I’m like, there might be something here. So then I kept putting them out, putting them out, and every single day more people would subscribe. And to this day, I think the wonderment of it all, I’m like, I can’t believe people are watching these things.

The vast majority of people, once they start skating, they feel free.

What do you think it is about roller skating in general that just seems to capture so many people?

Roller skating is a sport. But it also really bends towards the artistic. The vast majority of people, once they start skating, they feel free. They feel free and once they get that flow going, they start feeling freer and then they start moving their body in their own particular way. And they get to that point where it’s this form of self-expression.

That’s where it starts leaning towards the artistic side of things. And it’s so personal, there is no specific way you’re supposed to move your body once you get it to the free part. That’s why when I teach, I say, first, I teach mechanics, this is how you mechanically move your body to actually start rolling. Then I want you to be watching for flow. We put one element into another and see if we can get that to some sort of fluid state. And then the third thing I’m not responsible for you is style, that’s where you come in, where you are expressing your emotions through the movement of your body. That’s where it becomes magic, because think about it, there’s not that many other things that we do that can make us feel like we’re floating. Even though you may not look graceful doing it, you may not even feel it; you’re on your way. There’s something about giving in to the movement of the wheels, carrying you along and for a lot of people, it hearkens back to when they were children. Nobody ever put their skates on and just decided today would be the worst day ever, you know.

So I think it’s different than other sports because it has that artistic feel to it and that’s what makes it special, and then the other part of it is its solo pursuit that can be done socially. It’s interesting, you could be out skating with a group of people and you could be talking to someone and then just wander off naturally and it doesn’t seem weird. Do you have that experience when you go to the rink?

I actually had that exact experience at the skate park where someone was showing me something and once they thought I had it the energy was very, fly away little bird. But it didn’t feel awkward that we were together just rolling in different directions. I never noticed that.

So I love it because, for people who are not necessarily super outgoing, this is a sport that you can do solo in the company of other people, but you don’t have to interact if you don’t want to. You can be a part of the group, you can feel what’s going on with the group as it moves to the beat of the music, like a beehive, but you don’t have to go up and have conversations with people. We interact a lot even though we’re in a pandemic situation. With skating it’s comfortable to be around a large group of people doing the same thing but not feeling forced to talk to each other.

Do you think that freedom and that lack of pressure to socialize are what contributed to this very, very noticeable boom in rollerskating popularity over the summer?

Well, I think it’s what hooks people once they start skating, I don’t think they go toward it for that. I think, first of all, aesthetically, skates are pleasing to the eye. They’re just cute, like a really good bag that you’re never going to wear. You know that purse is just going to sit on that shelf but it’s going to make you happy.

I know exactly what you mean, my husband is a sneakerhead and I never got it but when I got my first pair, which are beautiful, I finally understood why people collect expensive ass shoes.

Skates are definitely pleasing, they represent fun and freedom, and I think when we all got locked down, it was like we all got put on detention and it was like, oh, now what am I going to do? And then we had a lot of skaters that were very loyal patrons to all these roller rinks around the country who started skating outside. Once that started hitting social media big time, like, oh, my God, all these people are outside and they look so free and they look like they’re having so much fun. Oh, my God, I want to do that, too. It’s accessible to so many people. If you can find some sort of flat space that isn’t dirt, you can skate.

So going back to your videos, you have what I would call a Skate-ism, which is this phrase you always bring up when you’re teaching about how to move your weight on wheels which is “down with the butt, up with the gut.” I think that’s absolutely genius, how did you come up with it?

I did not realize I said these things until YouTube. Literally, they were so ingrained in my instructions that I didn’t know why I said them until I would watch the edited video. Sometimes when I’m skating I kind of go on autopilot because I know what I’m talking about so it’s really easy for me to think, down with the butt up with the gut. But I learn a lot about how to explain movement from watching my students so I think at some point I was watching someone’s body mechanics and seeing that they were doing it correctly and then I would do it myself and really just sit with it and say, what is it I’m actually doing with my body?

I can’t believe these things that are coming out of my mouth. And then I was just well, you know, it says Dirty School. So hopefully people don’t get offended or whatever.

Honestly, when I first started I heard that phrase playing on a loop in my mind whenever I got stiff and it really helped.

My dad had the best saying! Whenever he would teach me and I would be doing figure skating jumps and I’d wipeout he’d say, “That was really good, just leave out that last step.” Which as a six-year-old trying to do a double axel I didn’t get but it’s like duh, leave out the part where you fell.

People keep telling me I should make a shirt that says the butt and gut thing, and the other word I use, “snack area.”

Yes! I love snack area because that is where all the snacks go! How did that come about?

You know what, I had to be totally honest because I knew I was going to be standing in front of people and telling them to tighten up their core. I really like to eat, and there’s some fat in [my core] area that I’ve just been hanging on to forever. So I thought if I get in front of these people and be like, you need to tighten up your core when I obviously have a fat gut, they’d wonder what kind of bullshit is this? So the idea is as I was teaching people live, I would be like, this is your snack area. Well, at least it is for me. You know, abs underneath, but I just got this layer of chub over it. So I just had to acknowledge it.

What’s the hardest thing to teach someone who is just getting started?

You know, that’s an interesting question, because the hardest thing to teach you would immediately think that that would be a skill, like the hardest thing to teach is backward skating or jumping. But probably the most important element of teaching is for me to very quickly at the beginning, be able to ascertain what it is that this person has doubt about within themselves? What are they afraid of?

So when I take someone on as a client within the first few minutes I’m trying to make a connection with them so I can figure out what’s scaring them right off the bat. The vast majority of people do not come and say, look, I already know what I’m doing and I just want to learn this one thing. Skating is a transformative activity. People come to skating because they want change and betterment in their life. I saw this with roller derby and I see this with recreational skating. The vast majority of people discover it in some form at a point in their lives where there’s been a change and they need to rediscover themselves or they need to do something different.

Probably the most beneficial thing in skating is not necessarily physical. I truly believe that skating self-esteem is derived strictly from achievement. If we are challenged and we overcome something, we feel better about ourselves, we’re like, holy shit, I did that! So when people come to skating, they’re almost always fearful of it because they don’t want to get hurt or they don’t know if they’re going to be good at it or they know they’re going to be bad. But they still want to do it. So when you get on your skates and you can even do the smallest thing like stand up or skate forward 10 paces or fall down and get up, they feel better about themselves. You’re like, oh, man, look what I can do. Often times when we’re out of school, there’s none of these measures that are kind of pre-made that say, hey, you did good. Like, no one gives you a report card anymore, right? When you go to work, you don’t get graded. When you go to work, you do work. And then if you do that work well enough, they’ll give you more work.

A lot of people are not getting kudos from what they really are putting hard work into on a regular basis. So when they come and skate, it’s such an organic thing. It’s real obvious when you do better. And it’s great when someone else says, hey, you did real good, but if you can tell yourself you did well, that’s the big thing. That’s the hugest thing like, oh my God, I did good, you know, and it’s crazy. It’s an emotional thing, especially as an adult, to be able to do something different and be successful in these little tiny victories along the way and see how it develops.

Wow, that is actually really sad to realize that once we leave the school system there really is no replacement for like the gold sticker. You just finish school and the world is like, we gave you all the assurance you’re ever going to get for the rest of your life.

Right? And prepare to be beaten down because even if you do a good job, you know no one really cares.

I think I had an experience like that where I was really down on myself because I couldn’t do a specific skate transition but I accidentally did another kind and the person helping me was like you did it! And I couldn’t be happy because I didn’t do the specific thing I wanted to do and they had to just verbally slap me and say, you said you wanted to do a transition and you did one right now, there’s no rule that you have to know how to do every kind of skate skill. Which was weird because my mindset is if I don’t know how to do every part of a thing, do I even really know how to do the thing?

So it’s funny how sometimes “thinking skaters,” people who really analyze and are thinking about it all, oftentimes they can do things that are more difficult. The skill you described to me is much more difficult than the one you were trying to do. So you just have to go with it. As you get better and there’s more time being put into skating, simpler things for you will just happen. They’ll come naturally. So look for things that you can do and really, really do them well and the other stuff will fall into place.

If tomorrow you could never teach or talk about skating ever again, what is the one thing that you would want to leave with your students?

That’s a huge question. I’m probably going to blab on and on, but I would say this: everyone become a teacher. Become a teacher and please set ego aside. Teach everyone you can, give away all of your knowledge. Don’t hold anything back. Our community is strong in numbers and the more people that we have doing it and the more people we have benefits our community as a whole. So many times I’ve heard people say they know how to do something, but they don’t want to show someone else how to do it. They don’t want to teach it to someone else. They do not verbalize this, but they don’t want someone to be better than they are. You know, they want to be good at this. They want to hold it close to themselves. This is what I can do. This is what separates me from other people. But I’ve had people contact me and say, hey, can I teach what you’re teaching? And I respond, of course! You could take it line by line, you can absolutely have it! I’ll send you the entire class written out. Take it, run with it, teach as many people as possible, because for me personally if you take what I do and you teach other people that helps me grow as a teacher. That’s how we grow, change and develop. If I am not consistently trying to grow, change and develop in organic ways, I will get frustrated just like anyone else. So as soon as you know a little bit about skating, try to teach someone else. Once you try to teach someone else, you will see skating in a whole different way and you will be surprised how much you learn from teaching. You’ll see how their body moves and it’ll unlock parts of your brain where you’re like, Oh, I see it now. So I encourage everyone to, as soon as you know something, teach it to someone else.

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