Lisbon is very good at setting the scene.
Unfortunately, a beautiful city cannot save every date.
1. The Rain, the Cobblestones, and the Heels
I had dressed for a cozy, beautiful dinner: a dress, heels, the right mood. He suggested we go for a walk instead. In the rain. On Lisbon cobblestones. I am still impressed I made it home without twisting an ankle. Since then, I have learned a practical lesson: even on the most romantic-looking date, sneakers are never a bad idea.
The truth is, Lisbon is not always kind to high heels, rigid plans, or overconfidence. But it is surprisingly generous with perfect dates — especially when you let the city do part of the work.
2. The Night a Date Turned Into a Football Incident
Once, during a slow evening walk with my date, a stranger stopped us to ask for directions. We said we did not know. He shouted “fucking Portuguese” and tried to start a fight with my companion. I was so frightened I cried. Later I realized Portugal had beaten Italy in a football match that day. He was probably Italian. Not every Lisbon date becomes memorable for the right reasons.
3. The Man Who Trusted Google Maps More Than Me
After one date, my companion suggested we keep walking. I said I loved Jardim da Estrela — it is right by my home. He opened Google Maps, checked something, and announced that the park was closed. I told him that had to be wrong; I walk there all the time. He was unconvinced. We said goodbye, he went home, and I spent another lovely hour walking in Jardim da Estrela without him. We never saw each other again.
At least Lisbon gave me the scenery.
The rest was character development.
Looking for date ideas in Lisbon? Try this out!
