• Keeping Friends

When an irresponsible friend asks for money

Published: October 8, 2015 | By | 14 Replies Continue Reading
An irresponsible friend is threatened with losing his home and asks a friend to bail him out. Because he’s helped her in the past, what does she owe him?



I’ve been dealing with some issues with my best friend of about four years. Mike has been my good/best fabulous gay friend for a few years, and has always been a bit dramatic. He is 24, lost his father at a young age, and his sister as a pre-teen.

He and his mother received a lot of life insurance money and they blew it all very quickly and have remained very financially irresponsible. He dropped out of high school, never worked much, always quit after a few short months. He parties all the time, drinks a lot, sleeps all day, and expects his mother to pay all his bills. Even in the house his father left them, which his mom doesn’t even live at, he expects her to pay the utility bills.

Now I am 26, was married at 20 to a marine, and was married for four years before we moved back home to build a house and start a family. Unfortunately my husband’s PTSD got the better of him. He asked me to move out and committed suicide four months later.

When I moved out, I moved into Mike’s house and he had supported me emotionally through that difficult time in my life. I stayed with him for eight months and then found an apartment right down the road. While I was living there, he and his mom asked if I could pay a little rent and I paid $200 a month to the town hall, to help with their back taxes. They were horrible about paying bills. The lights would get shut off or they would run out of oil. His mother’s truck payments weren’t getting paid and that state took money right out of her paycheck to pay her debts. The house that was paid for had a lien on it because they did not pay the property taxes.

Fast forward—another eight months to now. Mike had been receiving and ignoring mail from the town looking for money until he received a notice saying they had 30 days until the town auctioned the house. He called me, knowing I have money from my husband’s life insurance with the military, asking to help pay his and his mother’s debts. I told him to call other members of his family, the town, and a lawyer…and find out what was going on before calling me to bail him out.

His mother called me the next day asking for help also, needing $7,300 and I told her that while I didn’t care to hear the same contradictory blame on her son that he was blaming her for, that she shouldn’t be calling me just because she knows I have the money. I then told her to do some research, try and sell her motorcycle, call family, and the town and a lawyer, get her info and get back to me. I would try and help a little but I wasn’t just going to fork over the cash.

I know I would never see that money again and they had deliberately let this happen. Me bailing them out would solve absolutely nothing. His mother told him I said I was of absolutely no help, and it wasn’t my problem, so my friend started avoiding me. He acted like their situation was my fault and I did something to him.

He’s deleted my family and me off Facebook and blocked me on other social media. He told me he was going to drop off my weedwacker he had borrowed, and it seemed like he was ending our friendship over all this.

We got into a spat via texting when I reminded him that he owed me a couple hundred dollars because he asked me to buy him a shirt and tie for an interview (that he never even went to) and I rented his tux to be in our friend’s wedding. And he got really defensive about it and said something like, ‘If it weren’t for your husband dying you’d still be living in my spare bedroom.’

I even stated it seemed like he would never forgive me if he actually lost his house, and he admitted he wouldn’t have forgiven me even though he KNEW it wouldn’t have been my fault. Then he sent me a drunken text saying how much he loved me. Am I wrong to think that this narcissistic behavior is getting ridiculous?? I’ve never held him accountable for his own life, but he put me in a really bad spot with all this.

Signed, Wendy


Hi Wendy,

I’m so sorry for your loss of your husband, which must have left you reeling.

However, as an outsider, it’s hard for me to understand the basis for your relationship with Mike, which seems to have started while you were married. Although you call him a “fabulous best friend,” suggesting that you think highly of him, your description portrays him as someone who is moody, dramatic, dysfunctional and financially irresponsible.

Given that Mike seems to have risen to the occasion and was very supportive of you after your husband asked you to move out, I can understand how you would feel indebted to him for that. But your problems were situational and “time-limited” rather than chronic (ongoing). He made that decision to help you freely without strings attached and it doesn’t sound like it compromised his lifestyle in any way.

Fast forwarding to what it is being asked of you now—It seems like your friend and his mother have gotten over-involved in his family’s financial problems that have been festering for years. It sounds as if he and his mom are now financially destitute and need more help that you can reasonably be expected to provide. You were right to suggest that she figure out some plan to help them dig themselves out of this financial hole before handing over a large sum of cash that you aren’t likely to recoup.

In terms of your friendship, it sounds like you ignored many warning signs that should have suggested that this friendship would be a challenging one given your friend’s lack of financial responsibility. If your question is whether or not to stay involved, you will have to determine the emotional costs and rewards, and whether or not you will be able to establish financial boundaries so you don’t get sucked into loaning or giving away money you may need for yourself.

Hope this helps.

Best, Irene

Tags: , , ,

Category: Creating and maintaining boundaries, KEEPING FRIENDS

Comments (14)

Trackback URL | Comments RSS Feed

  1. Carlos B says:

    Loaning money or giving money? From experience, this is a great way to lose a friendship.

    Even when someone asks and you refuse or politely decline. They often will dislike you from that point on.

    If the amount is more than $50.00, don’t loan or give it away. Unless you expect to have the friendship changed permanently.

    If you feel that you must help them, write a contract and take collateral.

    • Mike says:

      if it was $50, I would swallow the loss. otherwise if it was a large amount I would probably use UOMOI again. sometimes losing people isn’t a bad thing especially if they’re toxic and hurting you

  2. DCFem says:

    I am truly sorry for the loss of your husband and I hope you are seeking counseling for your grief. I went to grief counseling after the unexpected death of my mother and it really helped me get on a path to healing and climb up from the depths of despair.

    The $200 reimbursement you asked your “friend” for is the cost of getting him out of your life. Forget the money and move on. This guy is an emotional vampire who will suck you dry if you let him. You have children to look after and no time to fret over an adult who could be doing a lot better if he really wanted to.

  3. Jared says:

    Tempest said it best, “Someone who really is a friend wouldn’t be putting you in a bad situation and then being petulant and nasty about it. Sorry, but he is a USER, not a true friend.”

    Asking someone for 7K is ridiculous and shows no class or sense of responsibility. It sounds like he doesn’t respect boundaries. Even if you lent the money, this guy would obviously push the boundary even further and expect something more intrusive at a future date.

    I wouldn’t want this type of person in my life. Period.

    I’m sorry for the loss of your husband and wonder if you are wasting your time with people who don’t deserve you. Any guy that can’t keep a job has problems.

  4. Sarah T says:

    Emotional Blackmail is: “If it weren’t for your husband dying you’d still be living in my spare bedroom” plain and simple. I used to have a friend that would play the “Don’t you know how hard my life is?” as a way to emotionally blackmail me into helping her. It never dawned to her (or she didn’t care) that her life is her responsibility. I refuse to be manipulated like that and worked on myself with a therapist to address boundaries.

    You are not responsible for other people’s problems. People who try to blame others for their problems have bad boundaries and are trying to manipulate people around them to get help at any cost. Whatever it costed others = it was worth it to get what they wanted.

    Like Irene stated above, a temporary problem is an entirely different animal than chronic dysfunction. Your “friend” Mike is trying to equate the two because he does not want to take responsibility for his actions/how he manages his life, is quite immature. Cutting you off because you didn’t help him is also VERY immature. You are entitled to put a boundary in front of him and the fact that he reacted that way is yet another sign of his immaturity.

    Boundaries are sooooo important to a persons self esteem/self worth and can weed out fools like this. Mike has shown you that he is not interested in a healthy relationship but only what you can do to serve him which is a self absorbed and an entitled way to live. You teach others how to treat you.

    At least you found this out now and can use it as an opportunity for insight and can enact change going forward.

  5. T says:

    Hi Wendy,

    I know how you feel regarding the friendship problem. But I dont think you should feel guilty because you did pay your way when you lived with your friend and his Mum, and they are the ones who lived like rock stars spending all the money, so that all their own fault really.

    I recently had a 6 yr friendship with a girl who I met at work. Our friendship blossomed until she lost her job and left. We carried on being friends and her and her husband went through stages of losing jobs etc. Slowly she started telling me that they were doing it so hard they had no food in the house even, and were about to lose their house because they were behind in the mortgage payments. She would ring me and say that every day she was waiting for the bank call to tell them their home had been repossessed. I suggested she sell before that happened, and go and rent. That would be the sensible thing to do. But no she said I have 10 animals and I cant afford to leave, as I cant take them with me to a rental.Every advice I offered she disagreed.
    I later learnt she and her husband were drinkers and drug smokers. Even though she initially said he was and she wasnt. But she slipped up a couple of times and let it out she drank with an alcoholic neighbour. I could tell by looking at her she was doing stuff, so I didnt beleive her after a while. Many times she hinted at me to help them with the mortgage payments, because she knows Im very good with money. We dont even earn alot and are on one wage etc. I still didnt offer, instead I said Im sorry but we have our own commitments and I couldnt help,but I know she was planning on getting some money from me. The whole six years was about me paying for lunches out, or supplying food when she came to visit me, she always made promises to contribute but never did.She also harped her husband was treating her badly etc, yet she was happy to stay with him when things were going well, and I wouldnt hear form her for ages.

    I have recently ended the friendship as I got sick of being given the hard luck story constantly all the time. I was recently asked to help with transport, when I live 40kms away from her. I just said sorry I have my kids to pick up and you will have to get your husband to help you. They blew up her mother’s car and paid nothing for it as her mother let them off, because they have no money. But she revealed they had certainly spent some money on themselves, for rediculous things sometimes. I didnt feel sorry that I didnt help her. She was in that postion because she actually bought a house she couldnt afford, with money she didnt have. She has too many animals to look after, but thats her choice. Lucky I didnt give them any money for mortgage payments, because I would never have seen any of it again. These people were leeches,making bad money decisions and expecting others to help them.

    Dont feel sorry for not helping people who dont deserve it Wendy, Your friend has to be responsible for his own financial situation they have created. Its not your problem to sort out.Dont give them any money. I would keep away from them too in future. You have nothing to feel guilty about.

  6. Susan M. says:

    I, too, offer my condolences regarding your late husband.

    You did pay a set, monthly amount, while you were living in your friend’s mother’s house. It seems that they both agreed to the monthly amount you paid. Therefore, neither of them should be comfortable in repeatedly bringing it up…which seems to be the case.

    Given all that you shared here, plus every thing you probably did not, can you list the reasons why this man, or his mother, deserve to continue being a part of your life?

  7. Maddie says:

    You are right in not giving him large sums of money and them asking for 7K was ridiculous. I would not have asked him for the 200 he owed you. He did open his home to you when you needed it and virtually for free.

    These people are too flakey and irresponsible to be involved with.

    I would have given them 300 dollars towards my past stay and waived the 200. Then I would have let the friendship drop.

    Sorry about your loss.

  8. Tempest says:

    Someone who really is a friend wouldn’t be putting you in a bad situation and then being petulant and nasty about it. Sorry, but he is a USER, not a true friend. You already know he is dragging you into his dysfunction, which is not a healthy place for you. If you hand over money you just enable more dysfunction. You don’t “owe” him – you paid rent! And if he acted as a friend at the time, great, but now he isn’t. If he’s willing to jeopardize your friendship to feed his dysfunctional lifestyle you are just better off stepping away. He doesn’t want to fix anything, just perpetuate his selfish immaturity.

  9. Lisa says:

    Wendy, first I want to say how deeply sorry I am on the loss of your husband at such a young age. You sound like a caring friend who offered advice to your friend and his mother. Sometimes the people we think are our friends are only our friends when we can give them things. These two individuals have the “entitlement” attitude. Don’t give them any money, if they are truly struggling I would buy them food (just don’t make this a habit also) and tell them you have to be responsible with your moey because you are dependent on you. For someone to cut you off because they don’t get what they want is childish and selfish, do you really want this stressful person hanging around you? Put your energy to better use and let these two get themselves out of the mess that they got themselves into. You are not to blame what happens to them, as you are not their mother. Thousands of dollars is a lot of money, and if you were to give it to them number 1 you would never see it again, number 2 you will have only bought them another year, as they would not change their ways and woud be in the same place a year from now, asking again for another 7,000. to bail them out. Mve forward not backward. They say you have to hit bottom before you realize you need to make a change. I wish you all the best in your life.

  10. Ben says:

    As others have offered, condolences on the your losses. We all go through life trying to negotiate the twists and turns. Having taken Ethics in college one learns that in many of the major issues there is no “black” and “white” simple answers. During the world-wide financial crisis starting in 2008 the term “moral hazard” was bantered about. The term refers to the danger of enabling irresponsibility by bail-outs. So what did we do as a country? We bailed them out thinking that was the best course of action. So be comforted in the fact that we as a country don’t take our own good advice. Some people never learn from their mistakes and many of us have to have dire consequences to get a wake up call. Regardless of whether those people ever apologize or make right what was done, you did what you thought was good and helpful for them. As long as you can look yourself in the mirror and like the person looking back that’s all that matters. There is a quote from Mother Teresa that basically says that our actions are not dependent on the outcome but the actions themselves are the important thing. Also like your former friends in the story not everyone gets good modeling growing up about financial responsibility or training in it. Just like in many cases of abuse in families there are stories of how generational abuse gets perpetuated throughout the ages.
    The best advice I adhere to regarding money is that if I have to give without strings or expectations I give it. I also know it’s important to practice being kind to those I do not like. Call it Karma or the law of sowing and reaping it’s all about doing unto others in a way that I want done to me. It’s really interesting to me to be around someone you know doesn’t like you and not react to their attacks. Kill ’em with kindness… Grace = unearned favor.

  11. Amy F says:

    Sorry to hear about your husband. That must be very painful for you.

    I’m not sure why you need to mention the fact that Mike is gay in your letter. What does sexual orientation have to do with the issues about money? I also don’t understand why you’re friends with this guy.

    If I were you, I’d find a therapist and/or support group to talk about the trauma of losing your husband in such a tragic way and your issues surrounding boundaries in friendships. You have a lot going on and could use the support.

  12. Sandra Anne says:

    I join the others in sending you sympathy on the tragic loss of your husband. You deserve a lot of TLC after all you’ve endured — and I hope you get it. It’s not going to come from your worrisome friendship with Mike. He and his mother have used you, and emotionally blackmailed you. That’s NOT friendship — or at least not a healthy one. Right now, you need to be strong and careful. This relationship with Mike is very complicated, somewhat dangerous, and possibly damaging for you. You deserve so much better!

  13. jacqueline says:


    My deepest sympathies on the loss of your husband. You have lived through so much, so young.

    I understand your feelings towards your friend, but giving him money is like throwing it in the garbage. You should not feel guilty about refusing to help financially. It is not his business that you have money from your husband’s life insurance. You could tell him that you will support him EMOTIONALLY, but you cannot dig into your pocket. He is using the fact that he took you in to play on your feelings. He still has not paid you back for the few hundred dollars he borrowed, imagine “lending” him thousands.

    I have a daughter who is financially irresponsible. Two years ago, she asked to “borrow” $8,000.00 from me in order to buy a car for her and her boyfriend. I told her I would be happy to give her anything from my heart, but not from my pocket. That was over two years ago, and I have not heard from her since. So, I am not advising you to do something I would not do myself, including for my own daughter.

    However, in the end, Wendy, you have to do what your instincts are telling you. Who will take care of YOU when the money is gone?

    Just my two cents.

Leave a Reply