border

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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
v.
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