Dilemma With a Homeless Woman


Wasn’t sure where to post this but it’s more of a spiritual issue for me than a financial one. I could really use some sound, sensitive advice (i.e., not knee-jerk reaction.) I apologize in advance for the length of this post, but it requires some explanation.

Not long ago I posted to the prayer thread on behalf of a woman who had lost her job and was homeless. Actually, this woman had worked part-time for the social service agency I work for and as it turned out, she had been homeless while she was working there. She lost her job when a kind-hearted client offered her the money to cover her co-payment for a medical appointment. Unfortunately, she accepted the money and the agency found out about it. Coincidentally, I had also quietly given her money for the co-payment. (She was in pain; how could I not?) I imagine that if I had been in her place, I would have done the same thing. Living hand-to-mouth, it would be very hard, even foolhardy, to turn down any offer of money. The agency I work for is in the charity district of a good-sized city. It’s an area where there are lots of homeless, lots of services for them, hospitals and social service agencies. Several times after she was let go, I saw her pushing a cart along a major street in that area. 10 days ago, she called and left a message for me a few minutes before the office closed for the day. In the message she asked for a list of resources and she said she was very hungry. If I’d thought about it I’d have known that if she’d been homeless for awhile in that area, she probably knew exactly what services were available and where to find them. She would also have known that I couldn’t get the resource info she asked for so late in the day. Our resource person was already gone and I didn’t know what services were available. I thought if I saw her I’d give her some money for a meal. Of course I saw her. She was walking the route I take home. The following Monday, I got the list of resources for her and left her a message to pick it up at the front desk. She never has. Since then, however, she has been walking by the office when I leave every day. She knows the schedule, she knows what days I’d be expected to leave early or later. It’s not a coincidence.

I’m not a particularly good judge of what Christian charity calls for in a situation like this. I have a younger brother who lived on the edge of homelessness for years, living in areas just like the one I’m talking about because he couldn’t keep a job for more than a few weeks. But he was my little brother, who our dad messed up emotionally big-time, and so he was always able to break my heart enough to get money for rent or food or whatever instead of facing the indignities of the social service jungle. He became very manipulative and I believe this woman is trying to do that now. The only women walking the streets in that area at the times I leave work are prostitutes. I hope to God she isn’t resorting to that. I’ve started being very creative in my routes home, driving through unsafe neighborhoods in order to avoid driving past her. This is ridiculous. I learned to be suspicious because of my brother. I can’t separate that from this. I want to do what’s right; it’s not that I don’t want to let go of money. I have more than I need. I don’t think she’s an alcoholic or a drug addict. She somehow manages to look nice and clean and fix her hair; she must be going to a shelter. Jesus said to feed the hungry when you see them, not drive out of your way to avoid them. I don’t know what to do; I don’t even know how to feel about it. I’m always the first person to advise not to give money directly to the homeless and instead to give it to the services that help them. That’s an easy rule to follow when you don’t know the person. I know this person walking the streets. She wants something from me personally. No matter how I handle it, I’m not going to feel good about it, so that’s not really important. I just want to do the right thing. I’d appreciate any thoughts you might have since I can’t seem to get past the experiences with my brother. Thanks.


Have you actually sat down and talked with this woman? I think that maybe getting to know her a bit better, invite her to lunch or to dinner and get her to talk about her situation, or if you don’t feel comfortable offering that type of charity right off, ask her to go to church with you where you can talk, sort of on neutral ground. Just because she is homeless does not mean that she is not human or not worth talking to, maybe she needs a friendly ear more than she needs the physical necessities of life, if as you say, she should know the resources and the places she can receive help.
Pray about what God wishes you to do above all, and pray that she may understand how hard it is for you to put yourself out as you do. Instead of leaving the list at the front desk I would hand it to her as you walked out, she may be embarrassed to go to the place she used to work as she is now. It would be quite awkward to walk into a place where you had once been employed to beg for services that you used to help others get. Being homeless in today’s society (especially in America) is in one way to be less than human and many people look down on those who are and she might know some people who work with you who feel that way. She reached out to you, I believe, as far as she could allow herself to, and I feel that maybe the next step for you is to trust God a little bit more and possibly open yourself up to this woman. You both will be in my prayers.


I agree with Hopeful23’s response. It would grandly humiliate a person to have to go a place to get help, where they were formerly employed.

The best thing to do is to deal with this terrible situation head-on, and speak with her face to face.


Dear FF;

Please get a trusted mentor or friend to help you in this situation. It sounds to me like this homeless woman is stalking you. She’s rejecting the help you feel comfortable giving (the list of resources, for example) and demanding that you give her what she wants.

Please don’t think I’m a heardhearted person with no pity for the poor. I’ve worked for the Church as a paid staff member and as a volunteer for many years and I’ve dealt with needy people of all kinds. Manipulators are the most pitiable and the hardest to help because they are so heard to reach. I fear that this woman might be one.

Do not meet her alone. Have someone come with you. Meeting at church is a good thing. If she is truly in need the two of you can figure out together what you can do for her.

Doing works of charity should fill you with peace not confusion. God bless you for your generosity.


Hopeful23 and musicadmirer,
I have spoken with her face-to-face; I know her, have worked with her. At the time she worked in my department, I didn’t know she was homeless but she was open about her poverty. That’s why I gave her money. I go from my “regular” job directly to taking care of an elderly man less than an hour later. I don’t have disposable time or I would have taken her somewhere to eat rather than giving her money for food. You may be right about her not wanting to come in and get the resource list. That hadn’t occurred to me because she doesn’t seem to have a problem walking right by the front of the building.

joan REDirector,
Thank you for sharing your concerns. I don’t think she’s dangerous and she’s not demanding anything. She’s just going to some length to be where I’ll see her when I leave every day. I’m not sure doing works of charity should necessarily fill a person with peace. It would be nice if it did, though.


I’m sorry that I don’t have much advice for you. However, I will offer you my prayers. I will say a couple of prayers for you and for this woman right now. :slight_smile:


IF she is trustworthy maybe you could have her help you with a visit or two to help your elderly friend. You could talk to her then and maybe help her find another job. That may be risky and you may want to clear it with your elderly friend first. Just a thought.


Dear FF

I still think you should have the advice of someone you trust in this situation. In your first post you say “…he (your brother) became very manipulative and she is doing that now.” Your instincts are right on.

But thank goodness you have people here praying for you. You sound like a very kind and generous woman. Since all charity is from God I assume that you are praying about this yourself. Turn again to the Gospels. You might start with Mark. Jesus is our best model of charity to the sick in body and spirit. The gospel writers say “… His heart was moved with pity.” But there were times Jesus worked no miricles although He could have. It may clarify things to ask yourself what Jesus wants for this homeless woman rather than what this homeless woman wants from you.

And DON’T link up this woman and the elderly gentleman you care for. If your homeless friend is confused and mired in the drug and prostitution culture the elderly man is in great danger from her. In her confusion and desperation she could do him harm.


you say she wants something from you, could be that she is lonely, has no family and sees you as a kind and compassionate person who helped her out .The fact that she is there when you leave work does lead me to agree with you about her wanting something from you, maybe she is hoping that you will offer to take her in and put a roof over her head (maybe this is way of track:shrug: what do i know) but she does want something from you. I will keep you both in my prayers and please God you will be able to come to a decision concerning this lady that will give you peace of mind. God Bless and good luck


A prayer said by Mother Teresa:

DEAR JESUS, help me to spread Thy fragrance everywhere I go. Flood my soul with Thy spirit and love. Penetrate and possess my whole being so utterly that all my life may only be a radiance of Thine. Shine through me and be so in me that every soul I come in contact with may feel Thy presence in my soul. Let them look up and see no longer me but only Jesus. Stay with me and then I shall begin to shine as you shine, so to shine as to be a light to others.

– Mother Teresa of Calcutta … pray for us!



Thanks for your replies and your thoughts. After a lot of reflection and talking to her a couple of times, I think I know how I should handle it.
First, though, let me respond to your comments and suggestions:

pia, you may be right about lonliness; she’s a loner by nature, I think, and when people are in the kind of situation she must be, they either draw into groups for support or they withdraw into themselves for protection. I think she falls into the second category. I can’t take her in even if I thought I could cope with it; right now I’m taking care of an elderly person on a live-in basis nights and weekends and working full-time during the day. It’s not my home and I have very little free time, in any case. But thank you for taking the prospect seriously. Not many people would.

Joan Redirector, you didn’t quote me correctly; I don’t know that she’s trying to manipulate me; I only suspect tht may be the case from past experience and behavior patterns. Unfortunately, I don’t know anyone who would consider helping a homeless person directly. My friends get pretty disgusted with me when my brother turns up with his hand out and I fold. That’s why I asked for suggestions and thoughts from CAF folks.

wcknight, it wouldn’t be a good idea to take a homeless person into the private home of a vulnerable elderly person for many reasons, not the least of which is the high proportion of mental illness and communicable diseases among the homeless.

We had an uncomfortable conversation yesterday; she was supposedly unable to get into a shelter because she’d lost her identification. I called the shelter that had turned her down and they agreed to take her if we’d send a photocopy of her driver’s license from our personnel file. So HR and I had our little covert operation and got her in. She wasn’t happy about it, nor about the long walk she’d have in order to get there. If she went, though, she had a hot meal and hopefully got a TB test, which she needs. She has never looked well to me. I offered today to take her to replace her ID but it had turned up. A gal in the office gave me some travel sized toothpastes for her and I picked up other toiletry and hygiene things for her at Walmart on the way home tonight. I’ll get them to her on Friday and offer to take her to lunch. Depending on how it goes, I may buy her a month bus pass so she’ll have a way to find a job and get to shelters more easily. I won’t give her money, though. Past experience tells me that once that starts, it doesn’t stop. I do want to help her so I need to use my head for something other than a hat rack, be up front and stick to my decision. It would be wonderful to see her employed; she’s 41. She doesn’t have much time to get her life straightened out. I suspect she’s been homeless for a long time. If anyone has any other suggestions
I’d appreciate hearing them.


You’ve done very well. Given her the help that’s appropriate and also the love and respect she needs. You are a kind and generous woman.


Good news! She has a job interview tomorrow. Please keep her in your prayers!


I don’t have any advice, I just wanted to say you are a very kind person, and reading your story really touched me. Thank you.


You are such a good person not everyone would take the time to help, you’ve also been such a God send to this woman and i would like to think that she appreciates everything you have done for her, but something tells me from what you have said and her reaction to you getting her somewhere to live that this is not the case.Stay strong and stick to you’re guns with regard’s to the help you give her, some people like this can drain you mentally without you being aware of it so be careful,as you say you already take care of someone else aswell as having a full time job you need to take care of yourself also.Buying her bus tickets and other things is so much better than giving her money and also taking her out for lunch once in a while just shows her that someone does care about her.I will also pray that she is successful in her job interview and that her health also improves. God bless


Dear FF,
I worked with the homeless in a shelter and was advised not to give money to the homeless. The one time that I did, I learned that he scamed me. After that I just gave them articles of clothing, shampoos, toiletries, etc to help instead.

Last year my daughter called me to say a girl who grew up two doors over was abused by her husband and needed a place to stay. I took her and her two children in for a week until they got a place in a shelter.

Then her sister visited while they were with us (my husband and I) and it turned out that she was homeless. I took her in when the sister left. She said she wanted to join the Catholic Church because that was where she had been baptized, but her mother quit taking her and she never even made her first communion. We got her enrolled in RCIA, which my husband and I teach classes in.

She never went to the classes, but was granted that we could teach her at home. Her initial interest soon died and things got strange as time passed. It turned out that she is on disability for migrane headaches and other problems. She cried about how she was a victim because she was abused by her step father from about age 9 to 13 or so.I felt terrible for her and sympathized with her.

As it got colder and winter arrived, she would hide in her room and we were concerned about her. She would accuse us of “slamming doors and stomping down the hall”. I gave her clothes, bought special food for her (that she let spoil) and we put rugs on the hall floor in front of her room.

Things finally came to a head the week before Easter when she started yelling at my husband for slamming doors and stomping again. He has a home office. I tried to reason with her, but it got really ugly with me finally telling her she could just leave if she did not like it there. She left that weekend.

That experience really disturbed me. I really wanted to help her, but she was not grateful for what we were doing to help her and complained too much making unfair accusations. I would really think twice before doing that again.



Yes, that all sounds very familiar; I’ve had strange experiences with my brother who was homeless and with a bi-polar alcoholic who decided that for some reason I was her best friend in the world. She happened to be related distantly to the wonderful people who practically raised me and I tried to help her out of gratitude to them. Pay it forward and all that. I learned my lesson. I stopped giving my brother money and I would only pay his bills directly to the landlord or utility, which made him really mad and I wouldn’t hear from him for months. It’s so hard; it breaks your heart. In general I agree with you about not giving money directly to the homeless. As I explained earlier, though, I knew this woman from work. It was a very sad situation and she zeroed in on my specifically. I did give her money for a meal the day she said she was hungry, but since have only given her toiletries and similar things. In any case, I haven’t heard from her. I don’t know whether she got the job or not. I posted this a few days ago but it didn’t go through for some reason - I may have embarrassed her or hurt her feelings. She came to the office twice looking for me even though I’d told her not to. My boss was kind about it, but told me I needed to tell her to stop. I did. Hard for me to judge whether I did it as kindly as I should have, but she hasn’t returned my voice messages. I did what I could and that’s all I can do.


Blessings on you for all that you do. It sounds like you have it together. I will be praying that she gets the job. And I will be praying for you.


Yes, please, everybody, keep her in your prayers. She still hasn’t answered my messages and I haven’t seen her anywhere on the streets in I guess about a week. Hopefully she got a job and was able to rent a room. Her cell phone has been turned off for a couple of weeks (the voice mail I’ve been calling belongs to a job search service for the homeless, I believe.); I’ll keep trying the cell, too and if service is restored, I’ll know she’s working. Although I hate that I might have offended or hurt her feelings, I’d rather she be angry and ignoring me than some of the other alternatives. It’s a rough neighborhood.


DISCLAIMER: The views and opinions expressed in these forums do not necessarily reflect those of Catholic Answers. For official apologetics resources please visit www.catholic.com.