"Just seeing Madrid coming into view, I was so ready to explore and meet new people"

I had the most amazing experience with making friends in Madrid. On the first tour I went on, I ran into two fellow solo travelers and they were incredibly kind and friendly. One was from the UK, the other California. After the tour we went out to lunch, and before we went our separate ways we agreed to meet up that evening to watch the sunset from what's supposed to be a great spot at the Temple of Debod.

When we met up later that day we made two more friends, from Germany and Italy, and went to dinner after a lovely time sitting on the grass taking in the new spring warmth and fresh air. It's been a long time since I laughed that hard and we had a really great time. We exchanged stories of our lives, cultural differences in our upbringings and in our careers. It was hilarious hearing them say 28 days was simply not enough PTO, where in the US you're lucky if you get 10 PTO days.

We all exchanged numbers, said our goodbyes, and went on our merry way. My new friend from the UK and I walked toward our Airbnb's together and had lovely conversations about our travels. This is when an unhoused man approached us. My typical response, based on my experience in NYC, is to not say a single word to the person approaching me and continue on my walk. If I'm followed, I give them a firm "No" and keep walking. Usually that settles it and I'm left alone. But this time, my new friend struck up a conversation with the man.

I said to him "Wow, you're a lot kinder than me, I wouldn't have engaged in a conversation like that." His response was, "He's still a human being." Which took me a second. I do a lot of preaching of not judging anyone because their life path might not be the same as yours, but here I'm coming across another one of my blind spots. I'm judging people based on their appearance and they're approaching me. So my lesson for me ever since has been trying to figure out the balance of making sure I feel safe - but also making sure I always lead with kindness.

I'm curious what others tend to do in these situations...