The complicated parts of being a woman, and other thoughts on homelessness

by Lesley on June 3, 2015 · 5 comments

in make-you-think

homeless man

Many years ago during my first job out of college, I became friends with a middle aged homeless man. His name was David, and he greeted me each day at the post office as I mailed packages for work.

David held a sign that asked for a smile or money, and I always gave the first and sometimes also the latter. For many months we exchanged greetings, sometimes talking in greater length depending on how busy I was. David was a little odd, but certainly kind, and while I didn’t understand why he was on the streets I did my best to show him compassion and love. For Thanksgiving I packed him up a bag of food, and occasionally I brought him dinner leftovers or a cookie.

I can’t remember what happened exactly, but after knowing David for a year he started making me feel uncomfortable. As a woman, I’ve learned to pay attention when the hairs stand up on my arms or my heart flutters faster than normal. While David didn’t seem dangerous, he was also a man on the streets and I was a young woman. When I started seeing him at the grocery store where I shopped, which was only a few blocks from our apartment, I knew my friendliness needed to be scaled back. I began looking for other places to take the mail, or going earlier in the day when I knew David wouldn’t be there. It was a slow break-up of sorts, sad and awkward but also necessary.

A few weeks ago, I took the kids to the post office by our house—the same one I frequented almost 10 years ago. Imagine my surprise when I noticed David sitting in the same spot next to the mailbox. His hair was still a bleached blond from the sun—or was it gray?—and his face was still tan but it wore more wrinkles than before. I hesitated before getting out of the car. Should I go inside? Would he remember me? Should I say hello?

As much as my I wanted him to know I remembered, my maternal instincts said otherwise. While it’d be extremely unlikely for him to hurt us, I needed to play things safe. Plus, he wouldn’t remember me, right? He very likely had some type of mental illness and probably watched hundreds of people go in and out of this post office for over a decade. I’ve aged. I have children. I’m just another face in the crowd.

When I reach the post office doors, I see him running over to me. My hands are full with children and he opens the door for me. We make eye contact for the first time and I thank him and continue inside. When I return outside and begin walking to the car, I thank him again. A few seconds pass and he yells, “I remember you, you know!”

I stop in my tracks, a kid in each hand. I’m not sure what to say, and I fumble in my words. Now is the moment when I can use his name—“David! Wow! Hello and good to see you again”—but I do not.

Instead I make an awkward comment asking if he’s been here a long time, and his eyes look crestfallen for a moment when he realizes I don’t remember or won’t remember.

“Yeah, it’s been awhile,” he says.

I smile and say it’s good to see him and then I head for the car. I am about ready to close my door when he yells, “I never forget a face like yours!” I back out and give a quick wave before driving away.

The whole interaction leaves me with so many questions. I question my judgment all those years ago, and then I question the walls I’ve since put up. I question if he’s really someone to fear, or just another lonely soul. I question if he remembers my kindness and compassion, or if he remembers my body and face. I’m a woman, after all, and things get a lot more complicated when a woman wants to care for someone living on the streets.

I think too many people fear or judge the homeless and don’t treat them as humans, but it’s also more complicated as a woman, and especially so when children are involved. There are real risks. How can we show love and kindness to those on the streets, even as women, even with our children nearby?

I’ve love to hear your thoughts and I plan to share more of mine next week.

Related post: The last day I walked away

Related Posts with Thumbnails

Oh my gosh this was such a good read.

I love how you put into words how different it is being brave in those situations when you have your kids. My kids simultaneously make me braver and  more fearful of outside dangers. 

I feel like as women we find ourselves feeling guilty if we don't offer a smile or a concession to every single person we encounter but I have to remind myself that's not my job. Doing what's right for you and your kids is never the wrong way to go.

Loved reading this <3


You should not feel guilty, Lesley.  You and your families safety should not be compromised by your compassionate nature. There will always be opportunities to share your love to less fortunate people, and display that love for others to your children.  This time was not one of them.


Love this, Les. As much as I hate to admit it, in the past year and a half I have had two encounters that basically jaded me towards talking to homeless men. One time, a man came up to me in a parking lot as I was buckling Everett into his car seat. He snuck up behind me while I was distracted and scared the crap out of me. I felt super vulnerable, his body was too close to mine, and I just remember feeling....uncomfortable. There was nobody else around and he was literally standing right next to me. 

The second time happened when I was driving at night, and I was sitting at a red light. A man came right up to my car and knocked on the car window asking for money. The only thing between us was a car window and it didn't feel like enough. My heart was racing as I drove away. 

In both of those instances, the men approached ME, rather aggressively, and invaded my personal space. This is, of course, a small sample of my interactions with homeless men, but it made me realize that I am much more comfortable talking to them when I feel more in control of the situation (ie - if I walk up to someone and hand them food, if I offer to buy them a sandwich in Jamba Juice, if I hand them a bag out my car window because I saw them standing there with a sign). Ever since those two encounters, I find myself just keeping my head down and ignoring most homeless men I see because I never know if/when they are going to overstep a boundary. I hate that I do this now, but I also don't really know how to push past it....

Thanks for writing about this. You made me think this morning ;)


It's a lot easier for me to have those interactions than it is for you, Lesley. And if I had mu kids with me when they were young I'd still be likely to handle it just as you did. Parenting comes with responsibilities. As the kids got older, though, I found myself engaging even if the kids were with me, like this time:

Life's needs shift, and I bet you'll find yourself shifting with them again.


  1. […] for our children to watch us model compassion to people on the streets, and after writing last week’s post I finally decided to sit down and share more about my thoughts on this […]