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border (up)on (something)

1. Literally, to be positioned next to something. France borders upon Spain to the south. That shed definitely borders on our property.
2. To share similarities with something without being identical to it. Be careful, some sections of this paper are bordering on plagiarism.
See also: border

work both sides of the street

1. Literally, to occupy positions on both sides of a single street in order to sell something to people walking on either side. Our sales were doing OK, but it wasn't until I hired a second food truck and started working both sides of the street that things really took off.
2. To aid, support, or engage with both sides of some issue, situation, agenda, competition, etc. Usually used with the implication of doing so in a duplicitous manner to benefit one's own interests or agenda, though not always. She was accused of working both sides of the street, acting as a legal adviser for groups trying to legalize recreational cannabis while also serving on the board of several organizations that have tried to quash actions. Look, I've been working both sides of the street in Washington for years, negotiating the rather volatile divide between corporate and political interests very carefully.
See also: both, of, side, street, work

border (up)on something

1. Lit. [for something] to touch upon a boundary. (Upon is more formal and less commonly used than on.) Our property borders on the lakeshore. The farm borders upon the railroad tracks.
2. Fig. [for some activity or idea] to be very similar to something else. (Not usually physical objects. Upon is formal and less commonly used than on.) This notion of yours borders upon mutiny! That plan borders on insanity.
See also: border, on

work both sides of the street

Engage in doubledealing, be duplicitous, as in The real estate agent was known for working both sides of the street, advising first the buyer and then the seller . This metaphoric term transfers opposite sides of a street to opposite sides of a negotiation.
See also: both, of, side, street, work

border on

or border upon
1. To be next to something in location: New York State borders on Lake Ontario. My property borders upon a small lake.
2. To come close to being something, especially in association, meaning, or intent; verge on something: Your harsh criticism borders on being offensive. Some of their jokes were funny, but others bordered upon the ridiculous!
See also: border, on

work both sides of the street

To engage in double-dealing; be duplicitous.
See also: both, of, side, street, work
References in periodicals archive ?
When the film was eventually made, the 24th Regiment magically became the South Wales Borderers.
Today it continues to serve as a shrine to thousands of fallen Borderers.
The Borderers extended the advantage in 73 minutes when Stuart Fraser headed a Noble corner out of reach of Grindlay.
Many campaigns had seen the South Wales Borderers distinguish themselves, particularly the battles at Isandhlwana and Rorke's Drift during the Anglo-Zulu War, in which many soldiers lost their lives.
He recalls how he almost drowned with the weight of his kit - which even included a bicycle - and tells a touching story of a French family who killed and cooked the pet rabbit of their son Michel to feed the Borderers.
But the Borderers hit back and Chris McLeod headed the equaliser in l6 minutes after good build up work by Andy McLean.
And only a reflex save by Andrews denied him a second when his fierce strike bounced in front of the keeper as the Borderers continued to press.
The Borderers finally got their reward as half-time approached when Danny Swanson was brought down by Steven Oates and McLeish netted from the spot.
It only became known as the South Wales Borderers some time after Rorke's Drift and the Isandhlwana battles.
I read with interest the story of the First Minister's visit to Zululand and the South Wales Borderers at Rorkes Drift?
The game was still in the balance when Park was whisked away - but two late tries by skipper Neil Hendry floored the Borderers and sealed the win for Ellon.
The advantage was shortlived as the Borderers levelled four minutes later courtesy of a Chris McLeod header which struck the underside of the bar before crossing the line.
Jimmy Crease's Borderers have now won four out of five and are unbeaten in six, but the defeat leaves Shire anchored in the basement.
The Borderers ended the visitors two game winning run and should have won by a bigger margin but again they lacked firepower in the final third.
The Borderers swept into a 14-0 first quarter lead with Anthony Jakeman and Fakahata Molitika scoring tries, both converted by fly-half Daniel Griffiths.