Its main meaning today is of purposeless activity, of fooling around, spending time aimlessly or dawdling or dallying.
The latest string of deals has shown that, even in the absence of a mouth-watering mega takeover, Mr Buffett is not one to lollygag around for too long.
Financial Times, 24 Jan. 2008.
Many American veterans will remember it, since it is part of the standard repertoire of insults used by NCOs to verbally chastise new recruits — in this case to accuse them of fooling around or wasting time. To American civilians, however, it sometimes has a subsidiary meaning of “to indulge in kisses and caresses”. This sense featured in a memorandum by the commandant of the St Alban's Naval Hospital in New York just after the end of the Second World War:
“Male and female personnel should only be together when conducting hospital business, and this should be in an orderly manner. Lovemaking and lolly-gagging is hereby strictly forbidden.” The expression “lolly-gagging” is a new one, even to most New Yorkers ... but the Thesaurus of American slang describes it as “A young man who lingers to spoon in a hallway after bringing his inamorata home.”
Truth (Sydney, Australia), 6 Jan. 1946.
It first appeared in the US about the middle of the nineteenth century. A wonderful sentence in an Iowan newspaper, the Northern Vindicator, in 1868 suggests that a lovemaking implication was around even in its early days: “The lascivious lolly-gagging lumps of licentiousness who disgrace the common decencies of life by their love-sick fawnings at our public dances”.
Jonathon Green, in his Cassell Dictionary of Slang, suggests it may come from a dialect word lolly, meaning “tongue”. If it is, then it’s a close relative of lollipop, which is also thought to come from the same source. Another spelling of the word is lallygag.