“Pertaining to” and “regarding” slip into business e-mails, legal briefs, and casual chats as if they were interchangeable. They are not, and the gap between them shapes clarity, tone, and even legal outcomes.
Misusing either phrase can blur responsibility, inflate syllable counts, and trigger judicial pushback. This article maps their histories, grammatical roles, stylistic footprints, and strategic uses so you can choose with precision.
Etymology and Core Meanings
“Pertain” drifts into English from Latin pertinēre, “to stretch toward, belong.” That sense of rightful belonging still steers the modern phrase “pertaining to,” which signals direct relevance or inclusion within a defined set.
“Regard” originates in Old French regarder, “to look at, watch.” The nominal form “regarding” keeps that observational nuance; it introduces a topic someone is looking at or thinking about rather than something intrinsically owned by it.
Because of these roots, “pertaining to” feels tighter, almost proprietary, while “regarding” feels looser, like pointing a finger at a subject.
Semantic Range in Contemporary Usage
Corpus linguistics shows “pertaining to” collocates with nouns such as “documents,” “rights,” and “procedures,” all of which can be constituents of a larger entity. “Regarding” clusters with “email,” “question,” and “conversation,” items that sit outside the speaker’s turf.
A quick test: if you can swap in “that belong to” without nonsense, “pertaining to” is probably safe. If “about” sounds smoother, “regarding” is the cleaner fit.
Grammatical Roles and Syntax
“Pertaining to” is a participial preposition that must modify a noun; it cannot head a clause. “Regarding” can act as a preposition and, in relaxed syntax, even as a sentential adverb: “Regarding, we need more data.”
Positioning differs. “Pertaining to” almost always follows the noun it modifies: “the files pertaining to the merger.” “Regarding” prefers the front: “Regarding the merger, see attached.”
Complement Types Each Phrase Accepts
“Pertaining to” rejects -ing clauses: “the rule pertaining to signing the form” jars native ears. “Regarding” accepts them smoothly: “guidelines regarding signing the form.”
Abstract nouns suit both, but “pertaining to” favors concrete, bounded nouns—contracts, parcels, invoices—while “regarding” happily fronts topics like strategy, morale, or vision.
Stylistic Tone and Register
“Pertaining to” carries a formal, sometimes musty aroma; it appears 3:1 more often in judicial opinions than in journalism. “Regarding” feels neutral-business; readers rarely flag it as stilted.
In customer-facing copy, “questions pertaining to your invoice” can sound standoffish, whereas “questions regarding your invoice” feels service-oriented.
Audience Perception Experiments
A 2022 UX study presented two FAQ pages to 400 users. The page with “pertaining to” scored 18 % lower on trustworthiness and 22 % lower on clarity. Same content, different preposition, measurable reputational hit.
Legal drafters sometimes want that extra formality to signal precision; marketers do not. Match the phrase to the emotional valence you need.
Legal Drafting: Precision vs. Vagueness
Contracts use “pertaining to” when drafters intend to rope in subordinate elements: “all intellectual property pertaining to the Device” sweeps in firmware, manuals, and trade secrets. Courts read the phrase as inclusive, not merely topical.
“Regarding” can create loopholes. A clause like “disclosures regarding the Device” has been interpreted to exclude internal memos that mention the device only tangentially.
One Delaware Chancery opinion reduced a damages claim by $40 million because the plaintiff could not prove the memos “pertained to” the asset; they were merely “regarding” it.
Red-flag Juxtapositions in Pleadings
Never pair “pertaining to” with “about” in the same sentence: “evidence pertaining to about the lease” invites motion to strike. Choose one prepositional route and drive it.
Replace strings like “pertaining and/or relating to” with a single preposition; judges hate rhetorical shotgun pleading.
Technical Writing and Documentation
API guides favor “pertaining to” when tagging metadata that belongs to an endpoint: “headers pertaining to authentication.” The phrase cues developers that those headers are constituent parts, not commentary.
User-facing release notes prefer “regarding”: “bug fixes regarding login speed” signals topical coverage without implying ownership.
Consistent usage within a doc set prevents ontology drift in automated parsing; mixing the phrases breaks regex filters that classify paragraphs by subject.
Micro-copy in Software Interfaces
Error messages use “regarding” to soften the sting: “We’ve encountered an error regarding your payment.” “Pertaining to” here would feel robotic and accusatory.
Tooltips that reference settings “pertaining to privacy” clarify that the toggle is part of the privacy subsystem, not just related chatter.
SEO and Keyword Relevance
Google treats “pertaining to” and “regarding” as stop-gap phrases with no direct ranking weight, but their surrounding nouns matter. Using the precise noun cluster after the phrase strengthens topical authority.
A blog titled “Laws pertaining to e-scooter insurance in Oregon” outranked a generic “regarding e-scooter rules” piece because the long-tail noun phrase matched searcher intent.
Avoid stuffing either phrase; one strategic placement near the 100-word mark satisfies latent semantic indexing without diluting readability.
Featured Snippet Optimization
Snippets prefer crisp question-and-answer formats. Frame the heading as “What laws pertain to e-scooter insurance?” then answer in twenty words, starting with “Laws pertaining to e-scooter insurance require…”
Keep the noun phrase identical in heading and answer; synonym swaps drop you out of snippet contention.
Email and Business Correspondence
Opening with “Regarding your last email” is now the default business salutation; it feels current yet polite. “Pertaining to your last email” sounds like a lawyer butting into a casual thread.
Use “pertaining to” in the body only when referencing attachments that are part of the main topic: “the invoice pertaining to purchase order 12345.”
Overuse of either phrase in a single message creates a fog of faux formality; swap in “about” or drop the preposition entirely when context is clear.
Threading and Searchability
Outlook and Gmail index the first three words of the subject line. A subject “Regarding contract amendment” surfaces faster than “Pertaining to contract amendment” because the keyword hits earlier.
Internal wikis that rely on prefix search benefit from front-loaded topics: “Regarding-Contract-Amendment-July-2024” beats buried phrases.
Academic and Research Writing
APA style prefers conciseness; “about” or “on” usually replace both phrases. When precision demands inclusion, “pertaining to” appears in methodological descriptions: “variables pertaining to socioeconomic status.”
MLA is more tolerant of “regarding” in discursive footnotes: “See Johnson regarding post-colonial readings.”
Grant proposals reward “pertaining to” when space is tight but ownership must be explicit; reviewers score proposals lower if scope language is loose.
Citation Signal Best Practices
Bluebook signals differentiate: “See” points to dicta, while “See generally” introduces background. Add “regarding” after the signal to clarify topic without claiming the source is authoritative for the exact proposition: “See generally Smith, regarding early lease termination.”
Never insert “pertaining to” inside a signal; it is not a recognized Bluebook connector.
Localization and Translation Pitfalls
Spanish translators render “pertaining to” as “perteneciente a,” which implies legal title; mistranslating it as “sobre” (about) can void exclusivity clauses. Conversely, “regarding” safely becomes “sobre” or “en cuanto a.”
Chinese contracts avoid participial phrases; both English terms often condense into the single character 关 (“related”). Without a follow-up noun, the scope expands unpredictably.
Always re-insert the full noun after translation to lock down meaning: “documents pertaining to the JV” → “关于合资企业的文件” plus an appendix list.
Machine Translation Training Data
Google’s publicly available parallel corpus misaligns “pertaining to” 12 % of the time, usually downgrading it to “about.” Feed the engine custom bilingual glossaries for high-stakes documents.
Post-edit samples focus on noun-phrase fidelity rather than the preposition itself; that is where courts look.
Accessibility and Plain Language
WCAG 2.2 recommends a ninth-grade reading level for public content. “Pertaining to” scores grade 14; “regarding” lands at grade 10. Replace either with “about” whenever feasible.
Screen readers voice “pertaining to” as three distinct syllables with secondary stress, slowing comprehension for visually impaired users. “Regarding” is two beats, easier to parse.
When the noun phrase is mission-critical and no one-word substitute fits, keep the formal phrase but pair it with a bullet list to break cognitive load.
Cognitive Load Metrics
Eye-tracking studies show readers fixate 40 ms longer on “pertaining to” than on “about,” enough to accumulate delay in long docs. Use the lighter form early, then layer the precise phrase once the user is mentally invested.
Average fixation time on “regarding” is only 15 ms longer than “about,” making it the safer middle ground.
Voice and Tone in Brand Style Guides
Slack’s voice manual bans “pertaining to” outright; it clashes with their casual vibe. Goldman Sachs permits it only in risk disclosures where legal precision trumps friendliness.
Mailchimp allows “regarding” in transactional emails but caps it at once per 300 words to prevent stuffiness.
Create a simple flowchart for writers: legal scope → “pertaining to”; user question → “regarding”; casual chat → “about.”
Micro-voice Differentiation
Sub-brands can share a parent glossary yet diverge on prepositional choice. A fintech’s blog for accountants may keep “pertaining to,” while the consumer sub-site swaps it out, preserving brand cohesion without linguistic monotony.
Document the rationale; inconsistent tone is the top complaint in B2B style audits.
Checklist for Rapid Revision
Open your document’s search pane. Type “pertaining to” and “regarding.” For each hit, ask: Does the noun need to feel owned, or just observed? Swap, retain, or delete based on that single distinction.
Next, run a readability check; target score 55–60. Any sentence above 25 words containing either phrase should be split.
Finally, read aloud; if you stumble, the preposition is too far from its noun. Move it closer or rewrite the clause.