It's true. Everybody does LUV Derek.
Somehow, some way, the most beLUVed guy on Park Avenue is . . . . the guy who hands out parking tickets!
Yeah, that's not normal. I tease him, as I have many times before, wondering how something so inexplicable, contrary to normal thinking, could be the case. "Have you sold your soul?" I ask.
He laughs. He knows I'm 99% kidding. He's wearing a mask, but beneath, I know there is that broad smile which so many people reference when talking about him. But it's not just a smile, it's a genuine smile. It's one of those smiles you either have or you don't. It's endearing and it fits him, his engaging personality.
Derek has worked with the Winter Park Police Department for 13 years. He grew up in Winter Park, attended Brookshire Elementary, Maitland Middle School and Winter Park High School, graduated in 2006. He is one of the most familiar faces on Park Avenue, can often be seen walking up and down the street, or parked handing out one of those golden tickets. It's not the kind the kids sought from Willy Wonka. And, yet, Derek may be just as LUVed as Mr. Wonka himself.
I ask him if working with the police was something he'd thought about before joining. "My grandma said when I was born, I was looking like a detective. My grandma said I think he’s going to be working for the sheriff’s department or police department one day. And look where I am now, with the Winter Park Police Department for 13 years. I LUV it."
If you work on Park Avenue, live in the area, it is likely you know Derek Tooley. And if you know Derek Tooley, there's a good likelihood you are a member of his unofficial fan club. Yeah, again, THE GUY WHO HANDS OUT PARKING TICKETS. That deserves repeating, emphasizing. This is not the way this story is supposed to go. But not everyone who hands out parking tickets it Derek.
Derek is as much a people person as anyone you will ever meet. "What I like about my job is I meet a lot of people. And you can’t beat working on Park Avenue in the City of Winter Park. What I don’t like about it is, of course, it gets hot."
I hear him say that and wonder if he sounds more like someone running for office or who should run for office. Either way, it's obviously sincere and I'd vote for him. I'm quite sure he'd win. I'm a relative newbie to the Derek Tooley fan club, but there are long term members.
Local Julie Von Weller has been a member a while. "I met Derek when I had Thread many years ago on Park Avenue. He was the antithesis of who previously held his job. Instead of simply issuing me a parking violation ticket for being in the loading zone, he stopped and asked how he could help me. You see, he noticed I was pregnant and struggling with unloading items for the store. He proceeded to grab a box and bring it into the store. It’s simple. He is a joyful person. He is full of humanity. He asks brilliant questions. Not just to ask them, but to get to know you. To understand you. His ability to connect allows others to be vulnerable and connect right back. He is the perfect example of community. The world needs more people like Derek. Heck, Winter Park needs more people like Derek. He really is the best. Hands down. Guy needs to be promoted. Triple promoted."
Ricci Culver, owner of Through the Looking Glass on North Park Avenue, tells me, "For a very long time, Derek has randomly stopped at my store to see how I was doing and if I needed anything. He is one of the kindest people you will ever meet. He just brings a smile to lightened up even the darkest days."
I post about him on Facebook before writing this and the comments are varied, but all glowing. Lots of references to his smile, lots of use of superlatives like amazing, wonderful, the best. Park Avenue LUVs Derek. And vice versa.
"Working on Park Avenue," he says, "it can’t get any better than that. I LUV Winter Park. The people, meeting everybody on Park Avenue. And, of course, everybody knows the parking guy, which is me. I’m well known around the City of Winter Park."
He says he does his job well, is obviously proud when he tells me he knows how to talk to people, make them feel comfortable about their parking.
I ask him to explain how there can be so much affection for someone who gives out parking tickets, as he's attempted with me before. Again, this is not the norm. I need to hear it again. It helps to see it in action. Okay, actually, it really gets easier to understand when you know and speak with Derek.
"Here’s the thing. It all depends on how you talk to people," he tells me, "how you explain things to them. You don’t just write tickets saying you can’t park there and then go. I take my time. And I explain to them why they got a citation for parking in a no parking zone. And they feel better. And I say, hey, there’s no points on your license, nothing against your registration. And so they brighten up when I tell them that."
He then tells me he's "one of the most LUVable, cool guys on The Avenue" and laughs. And I think, in my high school voice: Duh, gotta be to make this work the way it does.
He then shares a story about an individual who received one of those tickets in the past. "To be honest with you, I had a guy who stopped me at 7 Eleven one day who said you gave me a ticket one time, but you were so cool about it, I’m gonna buy your slurpy today." He laughs, and adds: "I was shocked myself. He said you were so polite, you were so kind. You took your time explaining it to me. You weren’t mean or nasty or rude about it."
I see Derek driving here or there, yell at him and wave. Sometimes I'll be driving along, yell at him from my car. I'm not the only one. "I get people who see me at the traffic light and they roll down the window and I’m like ‘Yes, sir,’ and ‘Yes, ma’am.’ Hey, you gave my daughter a ticket and you know, we just wanna say she’s not going to park there any more. But you were really cool about it. You just made our daughter feel cool."
Oh, yeah, THAT is completely normal: THANK YOU for giving our daughter a parking ticket. I begin contemplating the power of a smile and a kind, polite word.
"I actually get a lot of people who THANK ME for giving them a ticket." I can barely take it anymore, accuse him of being full of it. He laughs.
"I’ve been here for 13 years and I’ve never had anyone yell at me or curse me out." I tell him he's obviously missing out on part of what is supposed to come with the job.
"I’m sitting here on Park Avenue having lunch (310 & Prato are two favorites) and someone will come up and say, I don’t know you’re name but I see you here on Park Avenue all the time and you’re always smiling," he says. Always smiling. "This is just my personality."
I also note the part of his personality, his behavior which has him always addressing people as sir & ma'am. I didn't think he had any military experience, but that would seem to fit.
"It’s just respect," he says. "I don’t care how old you are, how young. It’s just the way I was brought up, to say yes, ma ‘am and no, sir. It could be a kid that’s 13 years old and I’ll say sir. It’s just the way how I was brought up, my dad being a Marine."
Derek's mom passed away on her birthday of this year due to colon cancer. Facebook makes us aware of such things in others' lives and, of course, we feel for them, knowing what they are going through. Knowing Derek and the sort of person he is, I felt even worse for him. Having come to understand just what an amazing young man she had raised, I felt she had to be pretty extraordinary herself. Derek tells me of her, "I wish my mom was alive to see this of me. I know she'll be very proud of me."
I'll admit to hearing women on occasion talk about how cute he Derek is, so I wonder, with all these connections, has he perhaps gotten a date from one of these ticket encounters. He says no. But: "I have not, but to be honest, I have had a lot of women who try to flirt with me to get out of getting a ticket. They wanna buy me coffee at Starbucks. But I say, no, ma’am, thank you, I’m fine."
He then talks about celebrities he encounters along Park Avenue and a fondness for Orlando Magic games. "The thing I LUV about Winter Park, you run into some celebrities out there. Like Carrot Top, he’s a cool guy. Doc Rivers, he comes through, a couple of the NBA players. Speaking of the NBA players, I’ve had one, hey man, I saw you before, but I left before you gave me a ticket. I say, how about a Magic ticket, man?"
Could someone get out of a ticket for a Magic ticket, I ask? "No man, if you’re wrong you’re wrong," he says.
I think about that statement and think about the extraordinarily wide variety of people who truly LUV this guy. I'm pretty sure that's a big part of his undeniable charm. No matter who you are, what your background, whoever you are, I'm quite sure Derek treats everyone exactly the same. That big smile is offered to all, just as it wins everyone over who sees it. It's also his shear LUV of life, the community he serves and represents.
"Working with the Winter Park Police Department – actually, for the City of Winter Park – we are known to do a lot of great things for the community. You never hear anything bad about Winter Park because we do things in Central Park and the kids, the residents, they all LUV Winter Park Police. It’s a great agency to work for and it’s a great place to work, to live."
I ask him if there have been significant changes he's had to deal with during Covid-19 and he mentions the smaller crowds, noticing a recent increase in traffic, which, he notes, "is good for businesses". He's wearing a mask with a United States flag and I ask him if this was something provided by the Winter Park Police Department or one he chose himself. "It’s something I chose myself. By working on The Avenue, it’s fashion out here. So, I like fashion myself. So, I thought, why not wear an American flag with my WPPD hat." I wasn't sure he'd respond just that way, but wasn't surprised. He adds it's good to look "fashionable while writing a citation."
Perhaps it's not surprising the most popular guy on Park Avenue is the guy who gives out parking tickets. As much as that might seem bizarre elsewhere, I'll admit, getting to know Derek more and more, sorta seems that's exactly how it should be here.
Everybody LUVs Derek. Impossible not to.