Certain cities embody such humanistic personalities that visiting them is like spending time with an old friend. Navigating familiar streets can feel as comfortable as catching up with a long-time friend while sipping cappuccinos. A valid understanding of a place transpires when you “meet” a city, especially one that has real character. The familiarity becomes knowledge, and the knowledge transcends into a sense of comfortability. Once you have met a city, its personality shines through, shaking off any doubt of the unknown and the city’s personal character begins to develop.

Portland, Oregon: the city where young people go to retire

Some cities display more personality than others, wearing their emotions on their sleeve, and some take time to get to know. There are cities that feel like melancholy women, enervated men, lonely lovers, lascivious ladies, feisty teenagers, or powerful politicians, and some, like Portland, Oregon, USA are children—naïve in their adolescence and unscathed by history’s overbearing weight.

There are cities that take on a strikingly female persona, like Milan, Italy, whose unscrupulous elegance is that of a debutant lady—striving to be elite and neglecting to acknowledge the unsightly parts of herself; or Buenos Aires, Argentina who is a sultry woman, mysterious and shy behind her beauty. Other cities are undoubtedly male, like Santiago, Chilé, who strikes me as a rich man of power, willing to sweep the social and political dust bunnies under the rug for the maid to clean; or Kuala Lumpur, Malaysia, the worldly diplomat with a closet full of nice suits—and secrets.

The first time I met Manila, I understood that she is like a broken hearted women—unforgiving, unruly and relentless, but eternally lonely, and just like a broken hearted women she weeps and prays. Manila was a magnificent city, the Pearl of the Orient. She was daring, bold, and successful—a true South East beauty—until World War II hit. The Battle of Manila left the city ravaged and torn. Once a thriving metropolis, the city wept sewer, her citizens prayed for their lost loved ones, and her sultry plazas and monuments were obliterated to rubble. Just like a heart broken lover, Manila has never been able to recover from her glory days. She has expanded and rebuilt, but the beauty that was once there disappeared with her soul. History has left her raw, exposed and vulnerable.

Some cities are so venerable that it takes longer to get to know their true character under their celebrated façades. Paris, France at first seems ladylike and self-assured, but after some time Paris’s true nature shows and suddenly you are reminded of the ironically funny, loud-spoken, and secretly insecure gay man who chatted your ear off about his expensive purse collection at a party one time.

There are cities, like Nuremburg, Germany, who are forever stamped with the mark of an event that it can’t live down making it impossible for any personality to overcome the extremity of the circumstance that remains emblazoned in the city’s very being.

Next time you meet a city, take the time to understand who she really is. A city’s personality is rooted in its history, people, traditions and culture. When you meet a city for the first time, the place is stripped of any preconceived notions you may have had from reading or hearing about it, and you are free to truly understand a place based from your own experiences.