Once took my partner on a surprise trip to Brussels for her birthday thinking "Brussels" was the English translation of "Bruges" (even put the tickets in a copy of "In Bruges" as a romantic gesture... 😐)
A good if embarrassing anecdote, but no history, beautiful architecture or chocolate, just technocrats, a wind that hollowed you out and museums that closed on a Sunday (who closes museums on a Sunday!)
A lot of the other places on here fall into the good bits/bad bits category - bewildered at the hate for Amsterdam (it's not just Dam Square FFS, of course that's horrible, but the museums and cafes etc are great, the houses, canals... but yes I preferred e.g. Utrecht), Berlin (simply a fascinating city, such a cool vibe everywhere, but I imagine off putting to people who say "naice"), Northern towns (generally so friendly)...
Worst I've been to is probably Marrakech: interesting but stressful, one wrong turn and you've walked into a hellhole with fly blown raw meat butchered in the streets and people washing clothes in holes, children in ill health, men starting at you menacingly. Not relaxing at all, not good if you like going off the beaten track, and (yes) not good if you're a woman (especially if you don't think you should respect local customs re: dress etc.)