The Worst Financial Mistake of My Life

It’s hard to be transparent, even with strangers on the internet. So it’s hard to discuss the worst financial mistake of my life. It’s not something you would typically hear. I didn’t buy a house in the bubble, charge hundreds of thousands of dollars to my credit cards, or lose big in a casino. I lost big in love, and it cost me.

What was the worst financial MISTAKE of my life?

The worst financial mistake of my life was getting involved with an alcoholic and staying with that alcoholic for over five years. I consider it one big never-ending mistake since it was the mistake that kept on giving. I was stupid, I didn’t know how serious of a thing alcoholism was, and I thought that I could help a friend.

Although I didn’t realize it at the time, I was in a financially abusive situation. He emotionally abused me, gaslit me, and manipulated me to gain and maintain access to my resources. I still blame myself for allowing it to happen and for not ending it sooner. However, I’ve come to understand that abuse victims aren’t always good at making rational decisions or seeing the situation for what it really is. 

Here’s where my story starts. 

I didn’t move Jonathan in with me to have a relationship with him. He was an old friend who was going through a tough time, and I thought I could help him get back on his feet by giving him a place to stay far from his hometown. I didn’t know the extent of his alcoholism (I also didn’t know about his bipolar disorder).

Eventually, our living together turned into a relationship. I did care about him, so much.   Maybe that is why I turned a blind eye to the alcoholism at first. Perhaps that’s why I let him treat me poorly for the first few years. I had built up this amazing image of him in my head, and when that didn’t coincide with reality, I made excuses.

My first mistake

So here’s where the financial disaster comes in. Jonathan didn’t work for the first few years we were together. I paid for all of the bills and our living expenses, and I even supported his beer habit. But he always had an excuse. It was a bad economy. The area we lived in wasn’t conducive to him getting a job. He wanted to start his own business. He couldn’t compete in the job market. And I, being stupid and naïve, believed him. I let him get away with it, again and again.

Unfortunately, that wasn’t the extent of my stupidity.  I gave him money for the business he was trying to grow out of the garage. He collected video games, and he’d buy them at garage sales and off Craigslist for low prices and resell them (but not on eBay, that was too much work, so he sold them to another dude who sold them on eBay). I would help him make a deal occasionally (more often than I’d care to admit), and he’d always promise to pay me back with the profit (sometimes he did, more often, he didn’t). Usually, he had enough money to keep his small business going and keep himself in alcohol and cigarettes. He never paid a dime towards living expenses.

Related: See how Partners in Fire is moving forward from this break-up

Having a job

J eventually found a decent-paying job with our neighbor’s company doing office work. He had to get up and go to work every day!  He worked from 6 am to 2 pm, and he was usually drunk by the time I got home. Sometimes, he wasn’t home when I got home, and I’d find him at the local bar, blowing his paycheck on shots (usually, he stayed home to drink). Even with this job, I didn’t see any money, but I was just glad not to be paying for his habit anymore.


I finally had enough in January of 2016, when he decided that he’d rather drink than go to work. It wasn’t good before this point, but I was holding things together.

His decision not to work was the first last straw for me. We broke up. He promised to try and do better. He would stay sober for a week, then a few days, then another week. But every time, he would go back to drinking. It seemed like he would do just enough to get me to stay with him.

By June of 2016, I had enough again. I ended it again and told him the only way I’d stay with him was if he went to rehab. He found a rehab facility that would take him (I paid for him to get on a health plan through the affordable care act – another colossal waste of money), and off he went.

He stayed in rehab for about 60 days. I was so proud of him! He quickly became a team leader and helped other people remain in recovery. He was ready to rejoin the real world and give up alcohol!  Woot!

After rehab

Unfortunately, his newfound sobriety only lasted for four days after he got out of rehab. He made up some story about why drinking was ok because he held himself accountable (they always have an excuse).

For the next six months, we were very on and off. I’d break up, he’d claim to try, I’d give him another chance, and then we’d be right back at square one. Then he confided that he knew he could quit drinking; he just had to face and overcome his biggest fear – a DUI he had gotten back when he was 20. He was terrified that he would have to go to jail over it.

Another mistake

I helped him (yet again). I lent him two thousand dollars to get a top DUI lawyer. He promised to pay me back a month later when he received his tax refund check. He had already siphoned about ten grand away from me by this point, so I didn’t want to give him the money. I didn’t trust him to pay it back. But, he needed the lawyer to overcome this one last thing, and if he waited, he might not be able to get him. So I lent him the money on the strict condition that he’d pay it back as soon as he got his check.

He got the check and gave the money to a friend of his who was “in a bad situation” instead of paying me back. This was the straw that broke the camel’s back. This was when I lost any trust that I ever had in him. Looking back, this was the point where our relationship indeed ended. This is what I still can’t forgive him for or recover from.

He did get the lawyer, though, and he could avoid jail with community service (which he completed!). But that didn’t stop the drinking. 


Still trying to make it work

I still stupidly tried to make the relationship work. I thought he could get better, even after all that, even after I knew I could never trust him again. When I got the transfer to Savannah, I told him that this could be our chance to start over. We would be in a new city, where he had opportunities!  He could make some friends and move forward with his life!

Unfortunately, that didn’t happen. The first few months in Savannah were a nightmare. But of course, I was to blame for it, because he didn’t have any friends. He couldn’t get a good job close enough to the house. He had nothing and no one in Savannah, so his only option was to drink.

I ended things with him again in October. I set up a Tinder profile and started dating other guys. J realized he was on the verge of losing me and started trying. He got a bus pass to get around town, signed up for a temp agency, and found a decent job. I didn’t give in right away, though.  I continued going on dates with other guys, and I told him that I wouldn’t even consider getting back with him unless he was sober for over 30 days. I also told him that it would be over if he drank ever again. However, I was driving him to and from work at this time; because it was far away from the bus routes, and he needed the job.

One last try

He made it the 30 days. He kept his job, started paying for some house stuff, and offered to do some demanding tasks around the house to start paying me back. Was he turning over a new leaf?  Was almost losing me the catalyst he needed to turn his life around??

I hoped so. I stopped dating other guys and decided to give him one more chance. But I wasn’t done making terrible decisions!  I knew that there was one major thing limiting him: his ability to get around. He was relying on either me or a less than reliable bus system. If he was going to make it, this was unsustainable.

And One More Mistake

So, I told him that I would help him get a car for Christmas. I meant that I would put 500-1000 towards a down payment or a beater. However, his credit was terrible. There was no way he could get something financed in his name alone. He fell in love with this used Kia, and although I felt uncomfortable co-signing, I let him pressure me into it. He promised that he would pay and work and that he would change and he wouldn’t screw me over. I didn’t exactly believe him, but I realized he didn’t stand a chance without reliable transportation, so I tried to believe him.

From December until our final breakup in January, things were shaky. He didn’t keep his word about not drinking, but I was terrified that he’d leave with the car and screw me over, so I didn’t break up with him. I did break up with him, and he threatened to do just that. He used the financial disaster of the car as a way to keep me with him.  

It’s really over

But a person can only take so much. I finally decided that I’d rather ruin my credit than let him hold me hostage over the car. I broke up with him and promised myself that I wouldn’t let him manipulate, threaten, or guilt me back into a relationship.

In addition,  I started seeing a therapist who helped me identify his manipulative behavior. And amazingly enough, I ended up meeting an amazing man who makes me feel like I’m the only woman on the planet.

Although looking back, I’m humiliated that I let myself be used for so long; I’ve been so happy since he moved out. I feel free. I feel like I can be myself again and relax in my own home! This past month of freedom has been indescribably amazing! 

And for anyone in a similar situation – Get out. Get out now. They won’t change. They will say whatever they think you want to hear so that they can continue doing what they want. Take care of yourself first. You deserve better.

26 thoughts on “The Worst Financial Mistake of My Life”

  1. Thank you for sharing your story. I can imagine how difficult this was to write. My father is a drug and alcohol counselor (sober himself for around 30 years) who has helped countless people over the years in AA and in rehab facilities and he always says the same thing that until someone wants to change for themselves, it won’t happen otherwise. I hope that Jonathan finds the help and strength he needs to get sober and stay sober, but that’s not up to you to do for him. It sounds like you made the right decision. I wish you luck and look forward to following the rest of your journey.

    • Thank you. I think it was the best decision for me too, even though it was difficult. I also hope he gets the help he needs.

  2. Oh wow. I’ve been following your blog for a while and knew something bad happened but I had no idea of the extent. I’m so very sorry you had to live through this. In the grand scheme of things, you will get past this financial mistake and be stronger and more successful in the long run because of it. Never stay with anybody that does not treat you like gold. Thanks for sharing this powerful lesson you learned. I hope it helps others avoid the same type of relationship and get out sooner.

    • Thank you. I think going through this did make me a stronger person, and I know without a doubt I will not settle for someone who doesn’t treat me right. Thanks for the kind words.

    • Thank you Angela! It wasn’t an easy thing, but I’m super glad I did it. Time to move forward!

  3. It’s very brave of you to share this story, I’m glad that it’s behind you and shares a *very* important lesson for other folks. Wow.

  4. Thanks for sharing your story and for helping others realise that these relationships are out there and how devastating they can be. So glad you got out and found someone who appreciates you. All the best with your future 🙂

    • Thank you! My goal in sharing this was to hopefully engage with people in similar situations, so that they know they can get out. Alcoholism is no joke.

  5. Thank you for sharing your story, and I am taken away by how people can take advantage of kindness.

    One of my friends from middle school / high school was arrested after breaking and entering one of his neighbors, who was a sweet old lady, tied her up, and ransacked her house. You just never know what people will do when alcoholism or drugs control them to be someone than you knew.

    • Thats so sad. I hope the lady was ok; even though that must have been traumatizing for her. It is awful that addiction can turn good people into unrecognizable shells of their former selves. The lengths that people will go to get that next fix is astonishing.

  6. Oh man….I could have written this. I too got involved with an alcoholic who started out as a friend. My husband had died, and he was a sympathetic shoulder at first. I realize now that he took advantage of my grief and loneliness. I broke up with him and took him back NINE times. Like you, I finally went to a therapist who helped me to see how codependent I was. I’ll never forget when she said, “He’s addicted to his alcohol and you’re addicted to him.” That was 6 years ago, and finally breaking free of him was the best and healthiest thing I ever did.

    • I’m glad you were able to break free as well! It’s terrifying how they suck you in, and make it so difficult for you to extricate yourself from the situation. Breaking free was one the best and healthiest things I ever did too. Best of luck to you!

  7. Until I sobered up, I was a mess and made a mess of relationships. I wish to apologize to all whom I hurt before I got sober, including relationships.
    I did sober up, and have been so now for over 40 years.
    The main thing I can tell you is that you were right to finally break it off. You write that you wish you had done it years earlier. I wish too that people would have called me on my drinking long before I figured it out myself.
    Congratulations on taking care of yourself, making yourself Number One.

    • It’s great to hear from the other side on this (I actually gave Jonathan the opportunity to tell his story on this blog, but he declined). Congratulations on being sober for 40 years! Thats an amazing achievement.

  8. I don’t think you were stupid, I think you were trying to help someone you loved. It’s a shame that he took advantage of your kindness in that way. Don’t beat yourself up too much about it, you were trying to be helpful to a person who needed it. Unfortunately, you can’t help people who don’t want to help themselves. I’m new to your blog, but I’m happy for you. It must be such a relief to take care of yourself and your own needs for a change!

    • “you can’t help people who don’t want to help themselves” is one of the truest things that I’ve learned out of this experience. Thank you for the kind words!

  9. That is an amazing story. And your last paragraph is a great reminder for those who are trying to find their way through a difficult situation. Substance abuse doesn’t only affect the abuser, it has a ripple effect on everyone involved.

  10. Wow. Points for transparency! May I suggest you find as many AlAnon meetings as your city holds and go to one every day? They’re for loved ones of alcoholics. Not for him, not for anyone but yourself, regardless if he is never again in your life or not. Speaking from personal experience, it can be incredibly helpful. You definitely kept overdrawing your account of trust for that guy! Best wishes to you in your own recovery.

    • Thank you for the advice! I haven’t gone to any Al-anon meetings, but a lot of you have mentioned it. Maybe I’ll give it shot!

  11. Have you heard of Al-anon? It is a very beneficial, free organization that’s sole purpose is to help people who have been affected by someone else’s drinking. The problems and history you had in your relationship are very common and it may help to discuss with others who have experienced the same thing. It will also help you with personal growth to ensure you don’t jump into a new relationship too soon or repeat past mistakes.

    • Yes, I have heard of al-anon. At first, I didn’t want to go because I felt like it was going to a support group for someone else’s problem. I didn’t want to admit that his problems really did become my problems. Seeing a therapist really helped a lot. Thank you for the advice!

  12. Great to hear you made it out of that situation. The greatest thing I learned from my similar-ish experience was I needed to acknowledge and confront my issue of enabling the behavior. I realized I was to blame and I couldnt pin it on the other party. If I didnt allow it then it couldnt have happened. After that life became amazing. I choose to be happy, I choose to be treated with respect, I choose to set clear boundaries, etc.

    • Thank you. I agree that I was to blame. The therapist really helped me identify my own codependent behaviors and heal from them. I learned that I can choose to be treated with respect!

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