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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 be very similar to something without being identical; to nearly be something. 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 such 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
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.

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
McGraw-Hill Dictionary of American Idioms and Phrasal Verbs. © 2002 by The McGraw-Hill Companies, Inc.

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
The American Heritage® Dictionary of Idioms by Christine Ammer. Copyright © 2003, 1997 by The Christine Ammer 1992 Trust. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.

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
The American Heritage® Dictionary of Phrasal Verbs. Copyright © 2005 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.

work both sides of the street

To engage in double-dealing; be duplicitous.
See also: both, of, side, street, work
American Heritage® Dictionary of the English Language, Fifth Edition. Copyright © 2016 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.
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References in periodicals archive ?
The Royal Cambodian Armed Forces (RCAF) cracked down on nearly 3,000 crimes along the Kingdom's borders in the first six months of this year, Ministry of National Defence spokesperson Chhum Socheat said on Wednesday.
It seems Armenia is not concerned absolutely that the state borders protection is one of the fundamental attributes of state independence.
He said although consultations were ongoing, the idea was to have the border gate opened at 06am and closed at 10pm to facilitate improved movement of people, goods and services between the two countries.
only, similarly Pakistani residents holding Qilla Abdullah NIC will be allowed to travel across the border for trade and business.
At present altogether 178 light buoys installed in cooperation with the Russian border guard this spring are marking the border regime area on the Narva River and Reservoir.
Unique ways to get drugs over the border have become more common in recent years as Customs and Border Protection has expanded its team and cracked down on smuggling.
We saw the border monitoring station, which is a hi-tech system to gather and interpret the border situation reports in real-time.
In relevant remarks in 2014, former Commander of the Iranian Border Guards Units General Hossein Zolfaqari underlined that his forces would use Unmanned Aerial Vehicles (UAVs) to patrol the country's borders.
TAE[currency]KENT (CyHAN)- A shootout took place on the state border of Kyrgyzstan and Uzbekistan June 29 between the two countries' border detachments, the Kyrgyz border service said.
Dark Purple Tone-on-Tone 3/4 yard for blocks, sash, border #'s 1 and 3 and binding
Another border skirmish has occurred on the Kyrgyz-Tajik state border in Leilek district of Batken region on the evening of August 25, the State Border Service of Kyrgyzstan told Turmush.
by Pajhwok reporter on 3 July, 2014 - 13:53 KABUL (Pajhwok): The European Union (EU) the other launched Border Management Northern Afghanistan (BOMNAF II) to continue the work of the successful BOMNAF I that enhanced the capacity of Afghan Border police to manage border posts, increasing security, fostering cross-border cooperation and opening of cross-border markets along the Afghanistan-Tajikistan border.
THE UNITED STATES AND MEXICO SHARE A BORDER THAT EXTENDS NEARLY 2,000 miles along the southern borders of California, Arizona, New Mexico, and Texas.
The possibility that terrorists and criminals might exploit border vulnerabilities and enter the United States poses a serious security risk, especially if they were to bring radioactive material or other contraband with them.