diff --git a/apps/calendar-macos/CompassKit/Sources/CompassKit/Life/LifeDateFormat.swift b/apps/calendar-macos/CompassKit/Sources/CompassKit/Life/LifeDateFormat.swift
new file mode 100644
index 0000000000..4c18cd19d4
--- /dev/null
+++ b/apps/calendar-macos/CompassKit/Sources/CompassKit/Life/LifeDateFormat.swift
@@ -0,0 +1,34 @@
+import Foundation
+
+/// Web `DatePicker dateFormat="MMM d, yyyy"` for the Life date of birth. The
+/// stored value stays `yyyy-MM-dd`; this only changes what people see and type.
+public enum LifeDateFormat {
+    private static let months = [
+        "Jan", "Feb", "Mar", "Apr", "May", "Jun", "Jul", "Aug", "Sep", "Oct", "Nov", "Dec",
+    ]
+
+    /// `2026-06-10` becomes `Jun 10, 2026`; anything else is returned unchanged.
+    public static func display(_ stored: String) -> String {
+        guard let date = LifeMath.parseLifeDate(stored) else { return stored }
+        let calendar = EffectiveTimeZone.calendar
+        let year = calendar.component(.year, from: date)
+        let month = calendar.component(.month, from: date)
+        let day = calendar.component(.day, from: date)
+        return "\(months[month - 1]) \(day), \(year)"
+    }
+
+    /// Accepts `yyyy-MM-dd` or `MMM d, yyyy` (comma optional) and returns `yyyy-MM-dd`.
+    public static func storedValue(from typed: String) -> String? {
+        let trimmed = typed.trimmingCharacters(in: .whitespacesAndNewlines)
+        if LifeMath.parseLifeDate(trimmed) != nil { return trimmed }
+        let parts = trimmed.replacingOccurrences(of: ",", with: " ")
+            .split(separator: " ", omittingEmptySubsequences: true).map(String.init)
+        guard parts.count == 3,
+              let month = months.firstIndex(where: { $0.caseInsensitiveCompare(String(parts[0].prefix(3))) == .orderedSame }),
+              parts[0].count >= 3,
+              let day = Int(parts[1]), let year = Int(parts[2])
+        else { return nil }
+        let value = String(format: "%04d-%02d-%02d", year, month + 1, day)
+        return LifeMath.parseLifeDate(value) == nil ? nil : value
+    }
+}
diff --git a/apps/calendar-macos/CompassKit/Sources/CompassKit/Life/LifeQuotes.swift b/apps/calendar-macos/CompassKit/Sources/CompassKit/Life/LifeQuotes.swift
new file mode 100644
index 0000000000..9e0039d78d
--- /dev/null
+++ b/apps/calendar-macos/CompassKit/Sources/CompassKit/Life/LifeQuotes.swift
@@ -0,0 +1,66 @@
+import Foundation
+
+/// Mirrors `LIFE_QUOTES` in `apps/calendar-web/src/views/Life/life-quotes.ts`.
+public enum LifeQuotes {
+    public static let all: [String] = [
+        "“Teach us to number our days, that we may gain a heart of wisdom.” (Psalm 90:12)",
+        "“It is not that we have a short time to live, but that we waste a lot of it.” (Seneca)",
+        "“How we spend our days is, of course, how we spend our lives.” (Annie Dillard)",
+        "“How many more times will you watch the full moon rise? Perhaps twenty. And yet it all seems limitless.” (Paul Bowles)",
+        "“Tell me, what is it you plan to do with your one wild and precious life?” (Mary Oliver)",
+        "“You could leave life right now. Let that determine what you do and say and think.” (Marcus Aurelius)",
+        "“Dost thou love life? Then do not squander time, for that is the stuff life is made of.” (Benjamin Franklin)",
+        "“As if you could kill time without injuring eternity.” (Henry David Thoreau)",
+        "“Time is the coin of your life. It is the only coin you have, and only you can determine how it will be spent.” (Carl Sandburg)",
+        "“Life is long, if you know how to use it.” (Seneca)",
+        "“Your time is limited, so don’t waste it living someone else’s life.” (Steve Jobs)",
+        "“The average human lifespan is absurdly, terrifyingly, insultingly short.” (Oliver Burkeman)",
+        "“Forever is composed of nows.” (Emily Dickinson)",
+        "“Time is the substance I am made of. Time is a river which sweeps me along, but I am the river.” (Jorge Luis Borges)",
+        "“Begin at once to live, and count each separate day as a separate life.” (Seneca)",
+        "“While we are postponing, life speeds by.” (Seneca)",
+        "“Nothing is ours except time.” (Seneca)",
+        "“Do not act as if you were going to live ten thousand years. Death hangs over you. While you live, while it is in your power, be good.” (Marcus Aurelius)",
+        "“Think of yourself as dead. You have lived your life. Now take what’s left and live it properly.” (Marcus Aurelius)",
+        "“It is not death that a man should fear, but he should fear never beginning to live.” (Marcus Aurelius)",
+        "“Seize the day, put very little trust in tomorrow.” (Horace)",
+        "“The Moving Finger writes; and, having writ, moves on.” (Omar Khayyam)",
+        "“To every thing there is a season, and a time to every purpose under the heaven.” (Ecclesiastes 3:1)",
+        "“Life can only be understood backwards; but it must be lived forwards.” (Soren Kierkegaard)",
+        "“The unexamined life is not worth living.” (Socrates)",
+        "“We are always getting ready to live but never living.” (Ralph Waldo Emerson)",
+        "“Lost time is never found again.” (Benjamin Franklin)",
+        "“Time is what we want most, but what we use worst.” (William Penn)",
+        "“The days are long, but the years are short.” (Gretchen Rubin)",
+        "“Spend the afternoon. You can’t take it with you.” (Annie Dillard)",
+        "“The trouble is, you think you have time.” (Jack Kornfield)",
+        "“It passes on just like this, not ceasing day or night.” (Confucius, watching a river)",
+        "“The months and days are the travelers of eternity. The years that come and go are also voyagers.” (Matsuo Basho)",
+        "“If not now, when?” (Hillel the Elder)",
+        "“We are such stuff as dreams are made on, and our little life is rounded with a sleep.” (William Shakespeare)",
+        "“As a well-spent day brings happy sleep, so a life well spent brings happy death.” (Leonardo da Vinci)",
+        "“The value of life lies not in the length of days, but in the use we make of them.” (Michel de Montaigne)",
+        "“Time and tide wait for no man.” (English proverb)",
+        "“The best time to plant a tree was twenty years ago. The second best time is now.” (Proverb)",
+        "“A man who dares to waste one hour of time has not discovered the value of life.” (Charles Darwin)",
+        "“We are like butterflies who flutter for a day and think it is forever.” (Carl Sagan)",
+        "“Nobody sees a flower really; it is so small. We haven’t time, and to see takes time, like to have a friend takes time.” (Georgia O’Keeffe)",
+        "“How wonderful it is that nobody need wait a single moment before starting to improve the world.” (Anne Frank)",
+        "“The purpose of life is to live it, to taste experience to the utmost, to reach out eagerly and without fear for newer and richer experience.” (Eleanor Roosevelt)",
+        "“I took a deep breath and listened to the old brag of my heart. I am, I am, I am.” (Sylvia Plath)",
+        "“The time is always right to do what is right.” (Martin Luther King Jr.)",
+        "“Don’t count the days; make the days count.” (Muhammad Ali)",
+        "“I urge you to please notice when you are happy, and exclaim or murmur or think at some point, 'If this isn’t nice, I don’t know what is.'” (Kurt Vonnegut)",
+        "“It is good to have an end to journey toward; but it is the journey that matters, in the end.” (Ursula K. Le Guin)",
+        "“Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.” (Ferris Bueller’s Day Off)",
+    ]
+
+    public static func random<G: RandomNumberGenerator>(using generator: inout G) -> String {
+        all.randomElement(using: &generator) ?? all[0]
+    }
+
+    public static func random() -> String {
+        var generator = SystemRandomNumberGenerator()
+        return random(using: &generator)
+    }
+}
diff --git a/apps/calendar-macos/CompassKitTests/LifeQuotesAndDateFormatTests.swift b/apps/calendar-macos/CompassKitTests/LifeQuotesAndDateFormatTests.swift
new file mode 100644
index 0000000000..7c889c8b59
--- /dev/null
+++ b/apps/calendar-macos/CompassKitTests/LifeQuotesAndDateFormatTests.swift
@@ -0,0 +1,36 @@
+import CompassKit
+import XCTest
+
+final class LifeQuotesAndDateFormatTests: XCTestCase {
+    private var savedZone = "UTC"
+
+    override func setUp() {
+        savedZone = EffectiveTimeZone.identifier
+        EffectiveTimeZone.identifier = "America/Denver"
+    }
+
+    override func tearDown() {
+        EffectiveTimeZone.identifier = savedZone
+    }
+
+    func testQuoteListMatchesWebAndEveryQuoteIsAttributed() {
+        XCTAssertEqual(LifeQuotes.all.count, 50)
+        XCTAssertTrue(LifeQuotes.all.contains("“Lost time is never found again.” (Benjamin Franklin)"))
+        XCTAssertTrue(LifeQuotes.all.allSatisfy { $0.hasPrefix("“") && $0.hasSuffix(")") })
+        XCTAssertTrue(LifeQuotes.all.contains(LifeQuotes.random()))
+    }
+
+    func testDisplayUsesWebsMonthDayYear() {
+        XCTAssertEqual(LifeDateFormat.display("2026-06-10"), "Jun 10, 2026")
+        XCTAssertEqual(LifeDateFormat.display("1999-12-01"), "Dec 1, 1999")
+        XCTAssertEqual(LifeDateFormat.display(""), "")
+    }
+
+    func testTypedDatesAcceptBothFormats() {
+        XCTAssertEqual(LifeDateFormat.storedValue(from: "Jun 10, 2026"), "2026-06-10")
+        XCTAssertEqual(LifeDateFormat.storedValue(from: "jun 10 2026"), "2026-06-10")
+        XCTAssertEqual(LifeDateFormat.storedValue(from: "1990-02-03"), "1990-02-03")
+        XCTAssertNil(LifeDateFormat.storedValue(from: "Feb 31, 2026"))
+        XCTAssertNil(LifeDateFormat.storedValue(from: "someday"))
+    }
+}
diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/Life/LifeSidebarView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/Life/LifeSidebarView.swift
index 4ef827fb29..75e9999817 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/Life/LifeSidebarView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/Life/LifeSidebarView.swift
@@ -8,6 +8,8 @@ struct LifeSidebarView: View {
   @State private var birthDate = ""
   @State private var lifespan = ""
   @State private var invalidBirthDate = false
+  /// Web `LifeQuote`: one random quote per visit to the sidebar.
+  @State private var quote = LifeQuotes.random()
   @FocusState private var focusedField: Field?
   private enum Field { case birthDate, lifespan }
 
@@ -38,7 +40,7 @@ struct LifeSidebarView: View {
               .accessibilityLabel("Date of birth")
               .focused($focusedField, equals: .birthDate)
               .onSubmit { commitBirthDate() }
-              .help("Enter a date as yyyy-mm-dd")
+              .help("Enter a date like Jun 10, 2026")
               .padding(.vertical, 8).frame(width: 176)
               .background(theme.surfaceColor).foregroundStyle(theme.textColor)
               .clipShape(RoundedRectangle(cornerRadius: 4))
@@ -69,7 +71,7 @@ struct LifeSidebarView: View {
         }
         .textFieldStyle(.plain)
         .multilineTextAlignment(.center)
-        Text("“Lost time is never found again.” (Benjamin Franklin)").italic()
+        Text(quote).italic()
       }
       .font(.rubik(14))
       .foregroundStyle(theme.textMutedColor)
@@ -97,12 +99,15 @@ struct LifeSidebarView: View {
   }
 
   private func refreshInputs() {
-    birthDate = model.lifeStore.preferences.birthDate
+    birthDate = LifeDateFormat.display(model.lifeStore.preferences.birthDate)
     lifespan = String(model.lifeStore.preferences.lifespan)
   }
 
   private func commitBirthDate() {
-    invalidBirthDate = !model.lifeStore.updateBirthDate(birthDate)
+    let typed = birthDate.trimmingCharacters(in: .whitespacesAndNewlines)
+    // An empty field clears the date; otherwise accept "Jun 10, 2026" or "2026-06-10".
+    invalidBirthDate = !model.lifeStore.updateBirthDate(
+      typed.isEmpty ? "" : (LifeDateFormat.storedValue(from: typed) ?? typed))
     refreshInputs()
   }