When does charity become problematic?

She smiled up at me in a way that reminded me of my little brother’s teenage girlfriend. It was a polite, good girl smile. Like she wanted to be likable.

Stepping outside of my office building after work, I noticed a girl sitting on the sidewalk with her back against the wall. She had a sign that read, “Please help, I’m sorry to ask.”
It was an especially cold night and I felt shocked seeing her there. I don’t remember seeing any other homeless people posted in that spot before.
She was young looking, she couldn’t have been that much older than me and she was pretty with a long skirt, a frail figure, and long straight hair. She was wearing a long billowy skirt and a hoody.
As people passed her by, she avoided eye contact. A businesswoman stopped to put money in her cup, a rarity in busy midtown Manhattan. My eyes teared up watching the scene.
I, not having any cash, turned towards my office building and went to the vending machine. Trying to go for the healthiest items I bought about five different snacks and headed back down.
When I neared her spot, I felt nervous. I suddenly realized that all of my items contained nuts.
I approached her with my items. Putting on my most cheerful and most feminine voice. “Excuse me,” I said. She smiled up at me in a way that reminded me of my little brother’s teenage girlfriend. It was a polite, good girl smile. Like she wanted to be likable.
I stumbled over my words suddenly feeling ineffectual. “Are you allergic to nuts?” I asked. She could see the abundance of granola bars I was carrying.
“No,” she said smiling back at me. The smile was understanding and reassuring like she could feel the anxiety I felt. I suddenly felt like she was doing me more good than I was for her. She was comforting my awkwardness.
“May I give these to you?” I held the snacks out suddenly realizing that I had not asked her what she needed and if she could ask for anything it probably wouldn’t be granola bars.
She nodded and, clumsily, I passed the snacks to her.
I started pulling out my phone, poised and ready for what came next.
“Feel free to say no,” I started, “but I’m a journalist and I was wondering if I could ask you a few questions?”
She looked at me, her smile not faulting but her eyes hinting at fear, or sadness, or something I couldn’t quite touch. She shook her head no.
Embarrassed, my cheeks flushed. I wished her a good night and left.
The exchange left me feeling guilty. I had wanted so badly to be a savior and here was someone who was the epitome of vulnerability. I felt creepy for my eagerness to help her and even worse because my idea of helping felt ultimately exploitative. If I weren’t writing this blog would I have given her a second thought? And would I have been so eager to help if she were ugly, or old, or a man?
I wondered if my help had even been wanted. Maybe she didn’t need food. Maybe she needed money for a room or ticket out of the city. Maybe she only needed money and why had I assumed that anything would have been better than nothing? In the future, I resolved to ask before I gave.