Everyone Who’s Ever Sold You Insurance is a Weirdo

Given my dirtbag upbringing, Lolita years, and eventual downward spiral of becoming a musician, I’ve spent a lot of time around weirdos and scumbags.

I’ve had to say, “Is this the bathroom door?” while pointing at a piece of moldy plywood that’s been propped up against a large hole in a wall.

I’ve had to say, “Cool python, Wack Max, but can you wait until after I leave to feed that rabbit to him?”

I’ve had to say, “Don’t mind me!” to a group of people shooting heroin in a kitchen so that I could reach into the fridge to grab a leftover rack of ribs.  Hey – they were from Bobby Rubino’s and I was really hungry from all that acid I had taken!

That being said…

Nothing could prepare me for the kind of weirdos that I would encounter in the years that I worked in insurance offices.

My truly fabulous mother-in-law just retired from the insurance business this month, so this one goes out to her.  Happy retirement, Patrice!  (She is the lone exception in the case of insurance weirdos.)

So!  Without further adieu, here is a non-exhaustive sampling of insurance coworker weirdos, because if I had to list all of them here, we would be here for five years still listing them off.  And I’m limiting it to coworkers, because if I even started to get into weird customers, this would go on for the rest of our lives.

Richie Sambora Guy:  This guy was not a fan of Bon Jovi – he was a fan of Richie Sambora, the guitar player from Bon Jovi.  His first day of work, he asked me, with his jaw clenched, if I thought Richie Sambora was “the most gifted guitar player of all time” so I, of course, said yes.  Because I could tell this guy was a *psycho*.  All he talked about, all day, every day, was how awesome Richie Sambora was and how unfair it was that Jon Bon Jovi got all the attention in the band.

When customers would come in and sit at his desk, he would casually ask, “So, what do you think about Richie Sambora?” and when they would say, “Who?  Is he an agent here?” or “He’s allright?” he would start flinging papers across his desk and stammering, “Well, I guess people are entitled to their own opinions!”

Old Woman Who 100% Stalked Me:  This woman not only rifled through my desk and my trashcan every night after I left work, listened in on my phone calls, and once asked me if she could go through my purse “out of curiosity”, but she used to peer into my car windows in the parking garage on her lunch break, and then come back into the office and question me about items that I had in my car.  “What’s with the frisbee I saw peeking out from under your jacket on the passenger side floorboard of your backseat?  And that phone bill has been sitting on your front seat for over a week now, I hope you don’t get a late fee.”  Good point, WEIRDO.  Who likes late fees, right?

Santana and Rob Thomas “Smooth” Woman:  Anytime this song would come on the radio, this woman would crank it up to 10 and angrily shush anyone who so much as uttered a sound for the duration of the song – including customers who were sitting at her desk asking questions about their homeowner’s insurance policy.  “Shhhhh!!!!” with a glare.  Every time it came on.  For two years.  When that song first came out, it was on like five times a day.

And speaking of!  Santana “Oye Como Va” Guy:  After a coworker who he didn’t like quit, this guy celebrated by pulling a Casio keyboard out of his desk drawer and playing Santana’s “Oye Como Va” on it, over and over.  A move I would have totally respected…

…except then he just started doing it anytime business was slow.  Every time he finished playing “Oye Como Va” he would say, “Would you rather hear some Billy Preston?”  Then I would say, “Yes!  Please!” then he would play “Oye Como Va” again.  (Please note, this was a completely separate insurance workplace and this guy was in no way affiliated with “Smooth” woman.)

Man Who Couldn’t Stop Talking About His Butthole and How Totally Not Gay He Was:  Within my first fifteen minutes at this job, the boss made sure to tell me, appropos of nothing, that his “butthole had a sign on it that said, “Exit Only!” and then laughed about it like the Joaquin Phoenix Joker for a full ten seconds before deadpanning, “I’m not gay.”

Then he reminded me of this butthole/not gay fact thirty minutes later.  And then another five times over the course of the morning.  I refused to laugh anytime he said it, prompting him to ask me where my “sense of humor was located.”

Had I thought of it at the time, I would have responded, “I would say your butthole, but I’ve heard that it’s “Exit Only.”

I worked at this office for half of one day before picking up my purse, pretending that I was just going to lunch, and then never returning.

Woman Who Looked Exactly Like Matilda The Hun from the Original G.L.O.W. Who Would Pick Up The Picture on My Desk of Me and My Sisters and Say The Filthiest Things Because She Didn’t Know That I Knew Enough Spanish to Know What She Was Saying:  I won’t even repeat the things she said.  They were straight-up, Larry Flynt would blush, absolute filth about what she wanted to do to me and my sisters.  She’d say this stuff and then lick her perpetually chapped, mustachioed lips and mouth-breathe at me, right at my desk, in my face. I never let on that I understood almost every word she said, because I did not want her to confuse this with “interest” on my part and then try to make me be her prison bitch. 

When she wasn’t standing at my desk, she used to stare at me from across the office while she squeezed Walgreens-brand petroleum jelly onto her finger out of a cap-less tube that she kept in a Ziploc bag, and then smear it on her mouth and go, “Mmmmm.”

Come to think of it, I’d never seen her and Matilda the Hun in the same room at the same time…

Also, she had her car repossessed from our parking lot on her first day of work, but that’s really neither here nor there.  Just an item of interest, it being her first day and all, as she was yelling, “You’re lucky my gun is still in New York, pendejo!” to the finance guy on the phone.

Please feel free to share your workplace weirdos in the comments, and then we will all laugh at their expense because we’re petty and mean-spirited.  Or is that just me?


Do you enjoy this crapola?  Click the Follow button if you do, and you’ll get a nifty email anytime I post this crapola.  If you don’t enjoy this crapola, might I recommend that you go into the insurance business?  You will meet some quality, non-weird people there.

“I’ve never bagged a babe.  I’m not a stud.” – Farmer Ted, Sixteen Candles

32 thoughts on “Everyone Who’s Ever Sold You Insurance is a Weirdo

  1. I’m almost speechless. Do weirdos like this exist everywhere or do you generate some kind of special attractant hormone? Of course, I shouldn’t say much… the woman who cranked up Smooth everyday for 2 years might be my long lost twin.

    Liked by 2 people

    1. I think it’s the combination of South Florida being a weirdo vortex in general and the insurance business being high on the fraud crimes list that it attracts so many weirdos. Or the lost city of Atlantis or something. Bermuda Triangle? 🤔

      Liked by 2 people

  2. I had a woman I worked with in an insurance office throw a whiteboard at me once.
    Oh, one more. Chick who lived in a low rent apartment comes in for renters insurance. Her apartment is “broken into” that same month. Tells the claims adjuster she had a Rolex and pearl necklace taken. Yeah. No.

    Liked by 2 people

    1. Did she throw it like a ball or fling it like a frisbee?? Either way, that’s completely nuts!

      We had a guy who used to break his windshield about twice a month just to get a new one for free since there was no deductible. He just liked free stuff, even if it resulted in twenty claims a year.

      Liked by 1 person

      1. Frisbee. I think that’s the only practical way to do it except for end over end hatchet style.
        Backstory. She was one of those daddy bought me a new Mustang for my sixteenth birthday people who only worked part-time so that she could be seen. We had nothing in common.

        Liked by 1 person

  3. Worked with an insurance guy in 1980 who liked to tell dirty jokes and then leer at me and go “do you get it?” If I said yes, he’d ask me to explain it; if I said no, he would. Ughhh. Another insurance guy told me I looked like I was gaining weight & when I told him to MYOB, he said “get on a scale.” An underwriter asked me why I looked upset, so I told him about scale man & he forced him to apologize. Good times!

    But that all was mild compared to agency people… 😂😂😂

    Liked by 2 people

    1. I would be in jail right now over the “get on a scale” guy. That guy needs a beating, like STAT. I’ve had a bunch of those “no filter” types over the years and they’re one of the chief reasons I’ve left jobs where I was otherwise okay. I always wonder, how hard is it to keep your gross, gross comments to yourself at work!

      Liked by 3 people

  4. I used to work at Blue Cross and Blue Shield and the Century Village bus would stop there every hour on the hour. One of them stole a photo cube of you and your sisters as babies. Then I made a fake name plate that said Rebecca Weinstein. Everyone loved me

    Liked by 2 people

    1. What is it with weirdos taking up so much interest of pictures of me and my sisters?! I could understand if we were the Kardashians maybe…

      I mean, we are. I’ve actually been Khloe this whole time, I just wanted to write this blog under a pseudonym.


  5. Well Maggie, it does seem that you’ve encountered your fair share of work place weirdos per-capita. When I worked in a warehouse one of the other warehouse workers use to like to take out his false teeth during lunch…..while eating…..when we were all together in the lunch room. And the mofo wasn’t even 30 yet, but he was a complete ass and annoyed everyone, and the bosses son. So I’m pretty sure he got his teeth kicked in (literally) for being an asshole in some bar some night, and that’s the story of “Toothless Eddie.” lol

    Liked by 1 person

    1. False teeth before the age of 30 is something I’ll be pondering all evening. I share your theory on him having had his teeth kicked in.

      Your current coworker stories absolutely slay me every time you post. I’m still lobbying for you and me to live closer to each other so we can work in the same office.

      Liked by 1 person

  6. … I think I’m the weirdo at work. My favorite casual conversation subjects are end of the world preparations and my wolf dog who is adorbs I might point out. But I don’t share photos of him because I have an ancient phone, so you’ll just have to imagine his cute. 😉

    Liked by 1 person

      1. I just kind of assume anyone with megobucks will go to ground in one of their ridiculous houses with a generator and spend the apocalypse drinking wine coolers and watching Netflix.

        I’ve got a water source, water filtration system, various cooking methods, a ton of rice and beans and spices… but no way to heat our house. So I’m hoping the world ends in like May or June or something, sometime early enough to plant food but warm enough that I don’t freeze my tush.

        The food storage is treating us well right now though since I lost my job… the only things we really have to buy are perishables like eggs and Soda for my husband or if we want something in particular/have a craving. Haven’t figured out how to store eggs yet. Weekly grocery bill of less than $30 for the win.

        Liked by 1 person

      2. I was just watching a clip on YouTube of Emmy Made in Japan where she preserves raw eggs in some kind of pickling solution that keeps them for 6 months, and it worked! She cracked them open and cooked them up and they were only a little different than eggs that were fresh from her backyard chickens! I was amazed it worked.

        Liked by 1 person

  7. I’m 100% positive that those people in the Insurance game have clones working in the hospitality business.
    Or else it just takes a weirdo to want to work there and that would explain my many years with the hotel gigs.

    Also sometimes the customers are even weirder.
    See this is why I don’t like people.

    Liked by 1 person

    1. The customers truly were something out of the seventh circle of hell. Just the strangest, strangest people – all in different and inconceivable ways. I can only imagine how much weirder they get in the hospitality business!


  8. After reading this, I realize I’ve lived a sheltered life. The weirdest guy I worked with (other than right now, when my workmate is my husband and we share a home office) was probably a salesman at a car dealership, one of my first jobs back in 1984. He lived with his mom but never wanted to go home, so rumor was he slept in his car in the parking lot and the outdoor bathroom that was supposed to be for the convenience all the salesman, contained his clothes and personal care items, giving credence to the rumor that he pretty much lived at the dealership. He was in his 50’s. Currently, the weirdo I work with is my husband, who sings to his dog and cusses at his computer constantly.

    Liked by 1 person

  9. This is too damn funny! Love it. I worked recruiting peoole to sell life insurance at 100% commission. Oh the peeps I interviewed. Then there was the chick who worked in the office as a top sales agent. She was a compulsive liar who drove me nuts. She was known to accompany new agents on joint calls and end up getting all the commission that was supposed to be split. Snake that she was. She also lied about shit no one cared about. One day at a big meeting that was supposed to be team building where they tear everyone down and build them back up and bring everyone closer (puke, gag, etc), the exec guy who was brought in to motivate said something that set me off. I could not take it anymore. I stood up and outed that bitch as the liar that she was. She packed her office in the middle of the night – never heard from again. This one young sales guy walked into the office where all the office people worked. He pointed at me and yelled ‘You have some big kahunas!’ Lots of praise from the small fries for that one.

    Liked by 1 person

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