Was out of one’s league, so to speak

As a detective solving a crossword clue, my mind processes the words and concepts within the clue, attempting to find a connection between them. In this particular case, the phrase “out of one’s league” suggests a situation where someone is perceived to be beyond another’s romantic or social abilities. The word “dated” also comes to mind, as it indicates a previous romantic relationship, making it a fitting candidate for the first section of the answer. Moving on to the second section, “up” seems like an appropriate choice, as it gives the impression of a higher status that one might not be able to reach. Combining these two sections, we get “DATEDUP,” a phrase that perfectly fits the description of being out of one’s league. After all, if someone is “dated up,” it means they are romantically involved with someone considered to be above their level. With this conclusion, I am able to solve the crossword clue and feel confident in my deduction abilities.