diff --git a/CHANGELOG.md b/CHANGELOG.md
index 0f0911e3c41..087242cd678 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,6 +6,8 @@
 - Added a fully black (no matter the theme) color SASS variable `$euiColorInk` ([2060](https://github.com/elastic/eui/pull/2060))
 - Added `autoFocus` prop to `EuiTabbedContent` ([2062](https://github.com/elastic/eui/pull/2062))
 - Changed `popout` glyph in `EuiIcon` to look more like external link ([2064](https://github.com/elastic/eui/pull/2064))
+- Tweaked `SuperDatePicker` to make the start/end date selection more obvious ([#2049](https://github.com/elastic/eui/pull/2049))
+- Added `toSentenceCase` string service ([#2049](https://github.com/elastic/eui/pull/2049))
 
 **Bug fixes**
 
diff --git a/src/components/date_picker/super_date_picker/date_modes.js b/src/components/date_picker/super_date_picker/date_modes.js
index 5f0733024b8..16f9924bf0a 100644
--- a/src/components/date_picker/super_date_picker/date_modes.js
+++ b/src/components/date_picker/super_date_picker/date_modes.js
@@ -19,7 +19,7 @@ export function getDateMode(value) {
     return DATE_MODES.RELATIVE;
   }
 
-  return DATE_MODES.absolute;
+  return DATE_MODES.ABSOLUTE;
 }
 
 export function toAbsoluteString(value, roundUp) {
diff --git a/src/components/date_picker/super_date_picker/date_popover/_date_popover_button.scss b/src/components/date_picker/super_date_picker/date_popover/_date_popover_button.scss
index b779c68eccf..88046e593fb 100644
--- a/src/components/date_picker/super_date_picker/date_popover/_date_popover_button.scss
+++ b/src/components/date_picker/super_date_picker/date_popover/_date_popover_button.scss
@@ -4,26 +4,37 @@
 
 .euiDatePopoverButton {
   @include euiSuperDatePickerText;
+  background-size: 100%; // For the bottom "border" via background-image
 
-  $backgroundColor: tintOrShade($euiColorSuccess, 90%, 70%);
-  $textColor: makeHighContrastColor($euiColorSuccess, $backgroundColor);
-
-  &-isSelected,
-  &-needsUpdating,
-  &:hover,
-  &:focus {
-    background-color: $backgroundColor;
+  &:focus,
+  &-isSelected {
+    background-image: euiFormControlGradient();
   }
 
   &-needsUpdating {
+    $backgroundColor: tintOrShade($euiColorSuccess, 90%, 70%);
+    $textColor: makeHighContrastColor($euiColorSuccess, $backgroundColor);
+
+    background-color: $backgroundColor;
     color: $textColor;
+
+    &:focus,
+    &.euiDatePopoverButton-isSelected {
+      background-image: euiFormControlGradient($euiColorSuccess);
+    }
   }
 
   &-isInvalid {
     $backgroundColor: tintOrShade($euiColorDanger, 90%, 70%);
     $textColor: makeHighContrastColor($euiColorDanger, $backgroundColor);
+
     background-color: $backgroundColor;
     color: $textColor;
+
+    &:focus,
+    &.euiDatePopoverButton-isSelected {
+      background-image: euiFormControlGradient($euiColorDanger);
+    }
   }
 }
 
diff --git a/src/components/date_picker/super_date_picker/date_popover/absolute_tab.js b/src/components/date_picker/super_date_picker/date_popover/absolute_tab.js
index 542d59594b6..30269280f05 100644
--- a/src/components/date_picker/super_date_picker/date_popover/absolute_tab.js
+++ b/src/components/date_picker/super_date_picker/date_popover/absolute_tab.js
@@ -6,7 +6,8 @@ import moment from 'moment';
 import dateMath from '@elastic/datemath';
 
 import { EuiDatePicker } from '../../date_picker';
-import { EuiFormRow, EuiFieldText } from '../../../form';
+import { EuiFormRow, EuiFieldText, EuiFormLabel } from '../../../form';
+import { toSentenceCase } from '../../../../services/string/to_case';
 
 const INPUT_DATE_FORMAT = 'YYYY-MM-DD HH:mm:ss.SSS';
 
@@ -17,10 +18,13 @@ export class EuiAbsoluteTab extends Component {
     const parsedValue = dateMath.parse(props.value, { roundUp: props.roundUp });
     const valueAsMoment =
       parsedValue && parsedValue.isValid() ? parsedValue : moment();
+    const sentenceCasedPosition = toSentenceCase(props.position);
+
     this.state = {
       valueAsMoment,
       textInputValue: valueAsMoment.format(INPUT_DATE_FORMAT),
       isTextInvalid: false,
+      sentenceCasedPosition,
     };
   }
 
@@ -70,6 +74,11 @@ export class EuiAbsoluteTab extends Component {
             value={this.state.textInputValue}
             onChange={this.handleTextChange}
             data-test-subj={'superDatePickerAbsoluteDateInput'}
+            prepend={
+              <EuiFormLabel>
+                {this.state.sentenceCasedPosition} date
+              </EuiFormLabel>
+            }
           />
         </EuiFormRow>
       </div>
@@ -82,4 +91,5 @@ EuiAbsoluteTab.propTypes = {
   value: PropTypes.string.isRequired,
   onChange: PropTypes.func.isRequired,
   roundUp: PropTypes.bool.isRequired,
+  position: PropTypes.oneOf(['start', 'end']),
 };
diff --git a/src/components/date_picker/super_date_picker/date_popover/date_popover_button.js b/src/components/date_picker/super_date_picker/date_popover/date_popover_button.js
index 6b38af26a5e..7bd2165d653 100644
--- a/src/components/date_picker/super_date_picker/date_popover/date_popover_button.js
+++ b/src/components/date_picker/super_date_picker/date_popover/date_popover_button.js
@@ -67,6 +67,7 @@ export function EuiDatePopoverButton(props) {
         roundUp={roundUp}
         onChange={onChange}
         dateFormat={dateFormat}
+        position={position}
       />
     </EuiPopover>
   );
diff --git a/src/components/date_picker/super_date_picker/date_popover/date_popover_content.js b/src/components/date_picker/super_date_picker/date_popover/date_popover_content.js
index 79629bd5323..b42930a5a77 100644
--- a/src/components/date_picker/super_date_picker/date_popover/date_popover_content.js
+++ b/src/components/date_picker/super_date_picker/date_popover/date_popover_content.js
@@ -20,6 +20,7 @@ export function EuiDatePopoverContent({
   roundUp,
   onChange,
   dateFormat,
+  position,
 }) {
   const onTabClick = selectedTab => {
     switch (selectedTab.id) {
@@ -32,6 +33,8 @@ export function EuiDatePopoverContent({
     }
   };
 
+  const ariaLabel = `${position === 'start' ? 'Start' : 'End'} date:`;
+
   const renderTabs = () => {
     return [
       {
@@ -43,9 +46,11 @@ export function EuiDatePopoverContent({
             value={value}
             onChange={onChange}
             roundUp={roundUp}
+            position={position}
           />
         ),
         'data-test-subj': 'superDatePickerAbsoluteTab',
+        'aria-label': `${ariaLabel} Absolute`,
       },
       {
         id: DATE_MODES.RELATIVE,
@@ -56,9 +61,11 @@ export function EuiDatePopoverContent({
             value={value}
             onChange={onChange}
             roundUp={roundUp}
+            position={position}
           />
         ),
         'data-test-subj': 'superDatePickerRelativeTab',
+        'aria-label': `${ariaLabel} Relative`,
       },
       {
         id: DATE_MODES.NOW,
@@ -78,11 +85,12 @@ export function EuiDatePopoverContent({
               fullWidth
               size="s"
               fill>
-              Set date and time to now
+              Set {position} date and time to now
             </EuiButton>
           </EuiText>
         ),
         'data-test-subj': 'superDatePickerNowTab',
+        'aria-label': `${ariaLabel} Now`,
       },
     ];
   };
@@ -105,6 +113,7 @@ EuiDatePopoverContent.propTypes = {
   onChange: PropTypes.func.isRequired,
   roundUp: PropTypes.bool,
   dateFormat: PropTypes.string.isRequired,
+  position: PropTypes.oneOf(['start', 'end']),
 };
 
 EuiDatePopoverContent.defaultProps = {
diff --git a/src/components/date_picker/super_date_picker/date_popover/relative_tab.js b/src/components/date_picker/super_date_picker/date_popover/relative_tab.js
index 4bc14e02c6e..008913739e1 100644
--- a/src/components/date_picker/super_date_picker/date_popover/relative_tab.js
+++ b/src/components/date_picker/super_date_picker/date_popover/relative_tab.js
@@ -1,6 +1,7 @@
 import PropTypes from 'prop-types';
 import React, { Component } from 'react';
 import dateMath from '@elastic/datemath';
+import { toSentenceCase } from '../../../../services/string/to_case';
 
 import { EuiFlexGroup, EuiFlexItem } from '../../../flex';
 import {
@@ -10,6 +11,7 @@ import {
   EuiFieldNumber,
   EuiFieldText,
   EuiSwitch,
+  EuiFormLabel,
 } from '../../../form';
 import { EuiSpacer } from '../../../spacer';
 
@@ -23,9 +25,11 @@ import {
 export class EuiRelativeTab extends Component {
   constructor(props) {
     super(props);
+    const sentenceCasedPosition = toSentenceCase(props.position);
 
     this.state = {
       ...parseRelativeParts(this.props.value),
+      sentenceCasedPosition,
     };
   }
 
@@ -108,7 +112,13 @@ export class EuiRelativeTab extends Component {
           onChange={this.onRoundChange}
         />
         <EuiSpacer size="m" />
-        <EuiFieldText value={formatedValue} readOnly />
+        <EuiFieldText
+          value={formatedValue}
+          readOnly
+          prepend={
+            <EuiFormLabel>{this.state.sentenceCasedPosition} date</EuiFormLabel>
+          }
+        />
       </EuiForm>
     );
   }
@@ -119,4 +129,5 @@ EuiRelativeTab.propTypes = {
   value: PropTypes.string.isRequired,
   onChange: PropTypes.func.isRequired,
   roundUp: PropTypes.bool,
+  position: PropTypes.oneOf(['start', 'end']),
 };
diff --git a/src/services/string/index.ts b/src/services/string/index.ts
index efb8d00af88..6ed792e589c 100644
--- a/src/services/string/index.ts
+++ b/src/services/string/index.ts
@@ -1 +1,2 @@
 export { toInitials } from './to_initials';
+export { toSentenceCase } from './to_case';
diff --git a/src/services/string/to_case.test.ts b/src/services/string/to_case.test.ts
new file mode 100644
index 00000000000..58888c0d8ee
--- /dev/null
+++ b/src/services/string/to_case.test.ts
@@ -0,0 +1,17 @@
+import { toSentenceCase } from './to_case';
+
+describe('toSentenceCase', () => {
+  it("should return the same single word with the first letter capitalized for 'single'", () => {
+    expect(toSentenceCase('single')).toBe('Single');
+  });
+
+  it("should return all the words with ony the first letter of the first word capitalized for 'two words'", () => {
+    expect(toSentenceCase('two words')).toBe('Two words');
+  });
+
+  it("should return all the words with ony the first letter of the first word capitalized for 'opposite Of Sentence Case'", () => {
+    expect(toSentenceCase('opposite Of Sentence Case')).toBe(
+      'Opposite of sentence case'
+    );
+  });
+});
diff --git a/src/services/string/to_case.ts b/src/services/string/to_case.ts
new file mode 100644
index 00000000000..dd49167ce16
--- /dev/null
+++ b/src/services/string/to_case.ts
@@ -0,0 +1,13 @@
+/**
+ * This function returns the same string with the first letter of the first word capitalized.
+ *
+ * @param {string} strint The input string
+ */
+
+export function toSentenceCase(string: string): string {
+  // First lowercase all letters
+  const lowercase = string.toLowerCase();
+
+  // Then just uppercase the first letter;
+  return string.charAt(0).toUpperCase() + lowercase.slice(1);
+}