diff --git a/app/src/main/java/io/github/sspanak/tt9/db/wordPairs/WordPair.java b/app/src/main/java/io/github/sspanak/tt9/db/wordPairs/WordPair.java
index 97efa9ce..bc2cf100 100644
--- a/app/src/main/java/io/github/sspanak/tt9/db/wordPairs/WordPair.java
+++ b/app/src/main/java/io/github/sspanak/tt9/db/wordPairs/WordPair.java
@@ -24,8 +24,8 @@ public class WordPair {
 
 
 	boolean isInvalid() {
-		Text w1 = new Text(word1);
-		Text w2 = new Text(word2);
+		Text w1 = new Text(language, word1);
+		Text w2 = new Text(language, word2);
 
 		return
 			language == null
@@ -33,7 +33,7 @@ public class WordPair {
 			|| word1.equals(word2)
 			|| sequence2 == null || !(new Text(sequence2).isNumeric())
 			|| (w1.codePointLength() > SettingsStore.WORD_PAIR_MAX_WORD_LENGTH && w2.codePointLength() > SettingsStore.WORD_PAIR_MAX_WORD_LENGTH)
-			|| !w1.isAlphabetic() || !w2.isAlphabetic();
+			|| !w1.isWord() || !w2.isWord();
 	}
 
 
diff --git a/app/src/main/java/io/github/sspanak/tt9/ime/modes/predictions/WordPredictions.java b/app/src/main/java/io/github/sspanak/tt9/ime/modes/predictions/WordPredictions.java
index c3ffd364..220e2d5a 100644
--- a/app/src/main/java/io/github/sspanak/tt9/ime/modes/predictions/WordPredictions.java
+++ b/app/src/main/java/io/github/sspanak/tt9/ime/modes/predictions/WordPredictions.java
@@ -8,7 +8,9 @@ import io.github.sspanak.tt9.db.DataStore;
 import io.github.sspanak.tt9.ime.helpers.TextField;
 import io.github.sspanak.tt9.languages.EmojiLanguage;
 import io.github.sspanak.tt9.languages.Language;
+import io.github.sspanak.tt9.languages.LanguageKind;
 import io.github.sspanak.tt9.preferences.settings.SettingsStore;
+import io.github.sspanak.tt9.util.Text;
 import io.github.sspanak.tt9.util.TextTools;
 import io.github.sspanak.tt9.util.chars.Characters;
 
@@ -348,6 +350,23 @@ public class WordPredictions extends Predictions {
 	 */
 	@NonNull
 	protected String getPenultimateWord(@NonNull String currentWord) {
-		return textField.getWordBeforeCursor(language, 1, true);
+		// We are in the middle of a word or at the beginning of a new one. Pairing makes no sense.
+		Text after = textField.getTextAfterCursor(1);
+		if (after.startsWithWord()) {
+			return "";
+		}
+
+		Text before = textField.getTextBeforeCursor();
+
+		// We are at the end of word. The user is probably typing a compound word. We do not want to
+		// pair with the first part of the compound word.
+		if (before.length() > currentWord.length() && before.toString().endsWith(currentWord) && Character.isAlphabetic(before.toString().charAt(before.length() - currentWord.length() - 1))) {
+			return "";
+		}
+
+		return before.getPreviousWord(
+			!currentWord.isEmpty(),
+			LanguageKind.isUkrainian(language) || LanguageKind.isHebrew(language)
+		);
 	}
 }
diff --git a/app/src/main/java/io/github/sspanak/tt9/util/Text.java b/app/src/main/java/io/github/sspanak/tt9/util/Text.java
index fd5942f4..12e10be5 100644
--- a/app/src/main/java/io/github/sspanak/tt9/util/Text.java
+++ b/app/src/main/java/io/github/sspanak/tt9/util/Text.java
@@ -16,7 +16,11 @@ public class Text extends TextTools {
 	private final Language language;
 	private final String text;
 
-	private final static Pattern QUICK_DELETE_GROUP = Pattern.compile("(?:([\\s\\u3000]{2,})|([.,、。，،]{2,})|([^、。，\\s\\u3000]*.))$");
+	private static final Pattern QUICK_DELETE_GROUP = Pattern.compile("(?:([\\s\\u3000]{2,})|([.,、。，،]{2,})|([^、。，\\s\\u3000]*.))$");
+	private static final Pattern PREVIOUS_WORD = Pattern.compile("(?<=\\s|^)([\\p{L}\\p{Mc}\\p{Mn}\\p{Me}\\x{200D}\\x{200C}]+)$");
+	private static final Pattern PREVIOUS_WORD_WITH_APOSTROPHES = Pattern.compile("(?<=\\s|^)([\\p{L}\\p{Mc}\\p{Mn}\\p{Me}\\x{200D}\\x{200C}']+)$");
+	private static final Pattern PENULTIMATE_WORD = Pattern.compile("(?<=\\s|^)([\\p{L}\\p{Mc}\\p{Mn}\\p{Me}\\x{200D}\\x{200C}]+)[\\s'][^\\s']*$");
+	private static final Pattern PENULTIMATE_WORD_WITH_APOSTROPHES = Pattern.compile("(?<=\\s|^)([\\p{L}\\p{Mc}\\p{Mn}\\p{Me}\\x{200D}\\x{200C}']+)\\s\\S*$");
 
 
 	public Text(Language language, String text) {
@@ -58,6 +62,24 @@ public class Text extends TextTools {
 	}
 
 
+	@NonNull
+	public String getPreviousWord(boolean skipOne, boolean isLanguageWithApostrophes) {
+		if (text == null || text.isEmpty()) {
+			return "";
+		}
+
+		Matcher matcher;
+		if (isLanguageWithApostrophes) {
+			matcher = skipOne ? PENULTIMATE_WORD_WITH_APOSTROPHES.matcher(text) : PREVIOUS_WORD_WITH_APOSTROPHES.matcher(text);
+		} else {
+			matcher = skipOne ? PENULTIMATE_WORD.matcher(text) : PREVIOUS_WORD.matcher(text);
+		}
+
+		String word = matcher.find() ? matcher.group(1) : null;
+		return word == null ? "" : word;
+	}
+
+
 	public int getTextCase() {
 		if (isUpperCase()) {
 			return InputMode.CASE_UPPER;
@@ -97,6 +119,18 @@ public class Text extends TextTools {
 	}
 
 
+	public boolean isWord() {
+		boolean isApostropheAllowed = LanguageKind.isUkrainian(language) || LanguageKind.isHebrew(language);
+		for (int i = 0, end = text == null ? 0 : text.length(); i < end; i++) {
+			if (!Character.isAlphabetic(text.charAt(i)) && !(isApostropheAllowed && text.charAt(i) == '\'')) {
+				return false;
+			}
+		}
+
+		return true;
+	}
+
+
 	public boolean isEmpty() {
 		return text == null || text.isEmpty();
 	}