Shamelessly stolen from the “Movies where…” thread, which I avoided hijacking by posting here.
Even though I can only think of two examples of songs:
“Alison’s Starting to Happen” by the Lemonheads.
Some song by Harry Chapin, can’t remember the name.
“Dear Catastrophe Waitress” by Belle & Sebastian.
Showing my age here but there’s “Sugar Shack” by Jimmy Gimer and the Fireballs.
(circa early 1960’s)
My personal favourite:
Human League-Don’t You Want Me?
You were working as a waitress in a cocktail bar, when I met you
Kim the Waitress - Green Pajamas
Sometimes she comes with coffee
Leaning over pouring
I’d like to gently pull her to me
Kiss her with no warning
Seeing her some sunny Sunday morning
I’ve only ever heard Material Issue doing that one. Green Pajamas dd it first?
Kinky Friedman’s “Waittret.”
Waittret, please waittret
Come sit on my face.
Eating ain’t cheating
Lord, it ain’t no disgrace.
Brandy (You’re A Fine Girl), an oldie by Looking Glass
I Don’t Even Know Your Nmae - Alan Jackson (video with Jeff Foxworthy)
Well I was sitting in a roadhouse down on highway 41
You were wiping off some ketchup on a table that was done
I knw you didn’t see me, I was in a corner booth
Of course you weren’t my waitress mine was missing her front tooth
So I flagged you down for coffee
But I couldn’t say a thing
But I’m in love with you baby and I don’t even know your name
And that Reba song from over the summer… Somewhere Out There ?? (wasn’t very good).
Truth be told, if I searched long enough, I could fill this thread with Country Music songs with that theme.
“Frozen Puck to the Head,” by Captain Tractor.
He played in the minors, he was a puck stop
One day he drove into this truck stop
When he saw her above the crowd and the din
And his heart made a noise like a truck you forgot to plug in
Oh, I’m sorry I don’t know who did it first! I have the Green Pajamas version 
Great song.
A Better Place to Be. Great song.
His Only Need by Wynonna Judd, her first solo single:
Billy was a small town loner
Who never did dream
Of ever leaving southern Arizona
Or ever hearing wedding bells ring
He never had a lot of luck with the ladies
But he sure had a lot of good working skills
Never cared about climbing any ladder
He knew the way in a small cafe, found the will.
grumble grumble damn quick Dopers always beatin’ me
“The Ballad of Dorothy Parker”, one of the best songs Prince ever wrote. And that’s saying something.
Airline Amy by Al Yankovic.
How about C W McCall’s “Old Home Fill’er-Up an’ Keep On-a- Truckin Cafe”.
It was a really sweet series of TV commercials (for Old Home bread) played in the upper midwest in the late 1970s about a trucker falling for the truck-stop waitress. The commercials were so popular that an album with the song was released. Chip Davis provided the music (he went on to start Mannheim Steamroller), and McCall came out a year later with “Convoy”.