In a British sitcom I’ve been watching, a character describes his perfect date to a friend. He takes his beloved to a beach, they take a train so they can pre-game with drinks, they have a picnic, “go for a stroll along the prom[enade] and then a ‘99.”
What the heck is a ‘99 in this context? It’s not a wine vintage, as the character died in the 1980s.
That’s a relief. I thought it might’ve been them knocking back three 33s each.
What about this?
That song was written by the band as a tribute to George Lucas’s first film, THX 1138, a dystopian film in which people no longer have names, but “designations” made up of random letters and strings of numbers.
In the song, “99” is the “name” of the woman, whom the narrator/singer loves.
Only to be bought from an ice cream van by the seaside.
The name is a bit of a mystery, and doesn’t relate to anything like price.
A side note: the full size Flake bar will stick in many memories for its TV adverts (much less innocent than a seaside 99):
When I sold ice cream from a van in the 1960s, a small cornet was 4d, a large, 7d, and a 99 was 10d.
The equivalent today would be 33p, 60p and 82p. In fact they cost £3 for a cornet and £3.50 for a 99.
My guess would have been releasing red balloons.
Number 66 - are you in difficulties?
Oh my dirty mind immediately thought of a sex position. Reclined rear entry? 
There are various competing stories about the ice cream originating in a shop that was number 99 in its road, as well as other dubious explanations - it’s likely it was just a catchy name like with Heinz and the 57 Varieties thing.
I’m glad you explained this. I thought the statement was alluding to having sex. LOL
Am I the only one who thought the singer was referring to Barbara Feldon’s character in Get Smart?
I tried an ice cream cone + Flake at a Canadian ice cream shop once. It was fine, but nothing special. I certainly liked it better than the time I tried dipping French fries in a Wendy’s Frosty (which felt completely pointless).
Nope, she was my first guess as well.
Not at the moment, but thanks for asking.
Not surprised - a 99 is usually that fairly flavourless compressed-air soft serve stuff (it appears that, contrary to legend, that’s one thing we can’t blame on Mrgret Th*tcher)
I have always called Toto’s “99” The Love Theme from Get Smart".
The Toto song came out when I was in high school; as a kid, I’d watched a lot of reruns of Get Smart, and, to be fair, I thought of Barbara Feldon’s character, too, when I originally heard the song. It wasn’t until much later that I learned of the connection to THX 1138.