Red Robin is kind of hit or miss. Some restaurants are tasty, some have me retching before I can pay my bill. When it’s good it’s hard to beat.
The times I’ve been called boss I felt it was as a sort of nominally respectful address. If someone is being cryptic and sarcastic with me, rather than engaging me directly, well then I guess they’re packing around some baggage and they don’t need me to make their day any harder.
I have a part-time job at a hardware store and get addressed as “boss” a lot by folks in the trades, mostly by younger guys, but some older. Though I can’t know what’s going on in their heads, it sure seems like their intent is friendly respect.
My perspective from England.:
I am (rarely) called boss; it is always by young Afro-Caribbean or Asian men.
I don’t like it, because the the body language says more like:
“YOU my boss? Ha, what a joke!”
I have yet to object, but the day is coming.
I almost started a thread about this recently. I guy that I work with calls me this. He is a POC and I am white. We are pretty close in age and at the same level. We always got along great but that always made me a little uncomfortable. I found out it’s not just me that he says it to, so I wasn’t going to make a thing about it. I think it’s just his go to phrasing and there isn’t any deeper meaning.
I thought it was a South Asian thing. I work with acres of Indians and Pakistanis every day. They generally call me “Boss,” I generally call them “Sir.”
I’m a white guy, and don’t remember any times where another white guy called me “boss” even if I was their boss.
I am work-friends with a black guy (I’m not his boss) who said to me one day “Yessir, boss” and I immediately felt uncomfortable, and told him “Don’t say that, man” and he just laughed. It just struck me as wrong, and, sad to say, it’s no small part based on movies where a black guy says “Yessir, boss” to a white guy, usually in the context of slavery. So, I don’t like it for that reason.
A lot comes down to tone of voice. Calling someone, particularly a stranger, “chum” or “pal” can sometimes be a prelude to aggression.
And these are all terms between men. From man to woman, woman to man, and woman to woman, there’s a different range of possibilities.
When I was a young man in the service industry in the 80’s I used to call male customers “boss” and “chief” and a dozen other names as a way to be friendly, informal and to get the customer to relax knowing they were in good hands. Rather than a sterile and boring “Yes sir” I would say “Sure thing boss, I got ya.”
99% of my customers responded positively. I did have one guy who after I called him chief he said, “Thanks indian!” Another guy responded, “Thanks peon!” Both guys had smiles on their faces.
Once I got a job in a more formal workplace (a hospital), I never used the term again except with children, who generally think that it is funny.
As an adult, I don’t mind being called boss at all. I just take it as the guy being chummy.
I started noticing the use of “boss” more after NYPD Blue started airing, since they used it a lot, and the show was quite popular.
When I was in China, one of my employees always called me “boss”; it was a direct translations from Chinese, and Chinese will often use titles rather than names.
This is common among Mexicans, too, but I’ve never had an employee in Mexico, so none have ever call me “boss.” One of my family friends in Mexico was referred to as “el jefe,” and my then-wife was “la generala”; I’m still not sure who was superior to whom.
If somebody calls me boss I assume they’ve served time and that’s where they picked up the habit.
Why?
I deal with outgoing freight, and one of the carrier drivers kept calling me boss, so I finally said, “if I was your boss I’d fire your ass”. He’s now switched it up to “Bro-ham”. 
Sounds like a “failure to communicate.”
Back in 1981, when Pennsylvania still had state unemployment compensation “field offices”, I was hired as an intake interviewer and assigned to an “inner-city” office in Philly; I’m white, and the clientele and staff were predominantly black. Some of the younger black male claimants addressed me as “boss”, which made me a bit uncomfortable.
It indeed seemed like a friendly casual greeting, i.e. I didn’t detect any snarky, sarcastic, or malicious undertones. Nor did it seem obsequiously deferential. I was mostly bothered by the possibility that I was somehow coming off as officious, or giving off an obnoxious vibe that I was superior or “one-up”-- that I was unintentionally signaling “bossness”. It’s worth mentioning that my style was always friendly and non-confrontational-- the opposite pole of the bumptious “storm trooper” or “power-tripper”, to use the office’s own terms for self-important hardliners.
When I cautiously sounded out black co-workers about this, they all validated my assumption that it was indeed a commonplace friendly casual greeting. One woman in particular, who used to tease me about my “warm 'n wonderful” way of dealing with even troublesome claimants, emphatically told me not to read anything into it, and that it was nothing to worry about.
This doesn’t exactly clarify or solve the semantic and psychological significance of minority persons calling white persons in a “power relationship” “boss”, but I took my co-worker’s advice and stopped worrying about it.
I occasionally address younger men as ‘sir’. (Usually in the context of answering direct questions (yessir, nosir). I have no idea what they think about that.
Perhaps the next time a cashier addresses me as ‘boss’, I’ll try to drop a ‘sir’ or two to see what happens.
I’m not your “boss”, chief.
[it’s the same thing]
My last work team had a Filipina woman who always called our manager “Boss Man”, mainly to tease him. The word “boss” itself is of Dutch origin.
“early 19th century (originally US): from Dutch baas ‘master’.”
Just reading the title made me smile, because the first time I got called Boss, I was a kid and it was an old dude chilling on a dock in Florida.
Made me feel special, but it said more about the guy than about me: it said he was so casual, so confident, that he could treat everyone like they were the boss.
So when I hear it, it makes me as happy, as *chill, *as that guy was.
Santa Fe Grill was exactly what I was thinking when I saw this thread.
For those who don’t know, in New Mexico you choose your gas station by the burritos they sell. Santa Fe Grill is fairly high on the list, made to order burritos in a gas station.