diff --git a/packages/perseus-editor/src/editor-page.test.tsx b/packages/perseus-editor/src/editor-page.test.tsx
index 358f037df5..823f0a6c28 100644
--- a/packages/perseus-editor/src/editor-page.test.tsx
+++ b/packages/perseus-editor/src/editor-page.test.tsx
@@ -278,4 +278,62 @@ describe("EditorPage", () => {
             screen.getByDisplayValue(/Updated content from parent/),
         ).toBeInTheDocument();
     });
+
+    it("should call getStartWidgetOptions if available", async () => {
+        const onChangeMock = jest.fn();
+
+        const startRenderer: PerseusRenderer = {
+            content: "That's an onomatopoeia!",
+            widgets: {},
+            images: {},
+        };
+
+        render(
+            <EditorPage
+                dependencies={testDependenciesV2}
+                question={startRenderer}
+                onChange={onChangeMock}
+                onPreviewDeviceChange={() => {}}
+                previewDevice="desktop"
+                previewURL=""
+                itemId="itemId"
+                developerMode={false}
+                jsonMode={false}
+                widgetsAreOpen={true}
+            />,
+        );
+
+        const textarea = screen.getByRole("textbox") as HTMLTextAreaElement;
+        expect(textarea).toBeInTheDocument();
+
+        textarea.setSelectionRange(10, 22);
+
+        const select = screen.getByTestId("editor__widget-select");
+        await userEvent.selectOptions(select, "Definition");
+
+        expect(onChangeMock).toHaveBeenCalledWith(
+            {
+                answerArea: {},
+                question: {
+                    content: "That's an [[☃ definition 1]]!",
+                    images: {},
+                    widgets: {
+                        "definition 1": {
+                            options: {
+                                definition: "",
+                                togglePrompt: "onomatopoeia",
+                            },
+                            type: "definition",
+                            version: {
+                                major: 0,
+                                minor: 0,
+                            },
+                        },
+                    },
+                },
+            },
+            expect.any(Function),
+            undefined,
+        );
+    });
 });
diff --git a/packages/perseus-editor/src/editor.tsx b/packages/perseus-editor/src/editor.tsx
index d326963ca1..567a4ffd9a 100644
--- a/packages/perseus-editor/src/editor.tsx
+++ b/packages/perseus-editor/src/editor.tsx
@@ -150,6 +150,10 @@ type State = {
     textAreaValue: string;
 };
 
+export type StartWidgetOptionsContext = {
+    selectedText: string;
+};
+
 // eslint-disable-next-line react/no-unsafe
 class Editor extends React.Component<Props, State> {
     lastUserValue: string | null | undefined;
@@ -659,6 +663,7 @@ class Editor extends React.Component<Props, State> {
         const isBlock =
             CoreWidgetRegistry.getDefaultAlignment(widgetType) === "block";
 
+        const selectedText = oldContent.slice(cursorRange[0], cursorRange[1]);
         const prelude = oldContent.slice(0, cursorRange[0]);
         const postlude = oldContent.slice(cursorRange[1]);
 
@@ -672,8 +677,16 @@ class Editor extends React.Component<Props, State> {
         const newContent = newPrelude + widgetContent + newPostlude;
 
         const newWidgets = {...this.props.widgets};
+        const widgetEditor = Widgets.getEditor(widgetType);
+        const startWidgetOptionsContext: StartWidgetOptionsContext = {
+            selectedText,
+        };
+        const startWidgetOptions = widgetEditor?.getStartWidgetOptions?.(
+            startWidgetOptionsContext,
+        );
+        const defaultProps = widgetEditor?.defaultProps;
         newWidgets[id] = {
-            options: Widgets.getEditor(widgetType)?.defaultProps,
+            options: startWidgetOptions || defaultProps,
             type: widgetType,
             // Track widget version on creation, so that a widget editor
             // without a valid version prop can only possibly refer to a
@@ -860,7 +873,6 @@ class Editor extends React.Component<Props, State> {
         let pieces;
         let widgets;
         let underlayPieces;
-        let widgetsDropDown;
         let templatesDropDown;
         let widgetsAndTemplates;
         let wordCountDisplay;
@@ -920,8 +932,7 @@ class Editor extends React.Component<Props, State> {
                 }
             }
 
-            this.widgetIds = _.keys(widgets);
-            widgetsDropDown = <WidgetSelect onChange={this._addWidget} />;
+            this.widgetIds = Object.keys(widgets);
 
             const insertTemplateString = "Insert template\u2026";
             templatesDropDown = (
@@ -957,7 +968,7 @@ class Editor extends React.Component<Props, State> {
                 widgetsAndTemplates = (
                     <div className="perseus-editor-widgets">
                         <div className="perseus-editor-widgets-selectors">
-                            {widgetsDropDown}
+                            <WidgetSelect onChange={this._addWidget} />
                             {templatesDropDown}
                             {wordCountDisplay}
                         </div>
diff --git a/packages/perseus-editor/src/widgets/definition-editor.tsx b/packages/perseus-editor/src/widgets/definition-editor.tsx
index d5e6797fd7..76eb6b909f 100644
--- a/packages/perseus-editor/src/widgets/definition-editor.tsx
+++ b/packages/perseus-editor/src/widgets/definition-editor.tsx
@@ -7,6 +7,7 @@ import _ from "underscore";
 
 import Editor from "../editor";
 
+import type {StartWidgetOptionsContext} from "../editor";
 import type {DefinitionDefaultWidgetOptions} from "@khanacademy/perseus-core";
 
 const {TextInput} = components;
@@ -31,6 +32,18 @@ class DefinitionEditor extends React.Component<Props> {
     static defaultProps: DefinitionDefaultWidgetOptions =
         definitionLogic.defaultWidgetOptions;
 
+    static getStartWidgetOptions(context: StartWidgetOptionsContext) {
+        const defaultWidgetOptions = {
+            ...definitionLogic.defaultWidgetOptions,
+        };
+
+        if (context.selectedText) {
+            defaultWidgetOptions.togglePrompt = context.selectedText;
+        }
+
+        return defaultWidgetOptions;
+    }
+
     change: (arg1: any, arg2: any, arg3: any) => any = (...args) => {
         return Changeable.change.apply(this, args);
     };