6 Years Later – Reflecting on the Biggest Financial Mistake of My Life

Transparency is challenging, but sharing stories of loss, hardship, and failure is vital. These stories serve as warnings to others but also as catharsis. 

We’re all human, and we all make mistakes. Sometimes, a financial horror story that resonates with something happening in your own life can be the catalyst you need to make changes. 

Here, Melanie Allen, founder of Partners in Fire, shares the biggest financial mistake of her life in hopes of helping others realize they can overcome life’s biggest challenges. 

What Was The Biggest Financial Mistake of My Life?

The worst financial mistake of my life isn’t something you usually hear about on financial websites. I didn’t buy a house during a massive bubble, charge thousands of dollars to credit cards, lose big in a casino, or cash out a 401K too early. 

I lost big in love, and it cost me dearly. 

Choosing the Wrong Men

My biggest financial mistakes involved men. 

I trust quickly, love deeply, and see the best in people, even when they prove me wrong again and again.

My five-year relationship with an alcoholic proved to be the worst decision of my life, impacting everything from my mental health to my financial well-being. 

Starting as Friends

J (as we call him on this website) was a friend for a long time. We met during my first year of college. He was a townie, but we were the same age and had instant chemistry. 

We stayed friends over the years despite each flowing in and out of the town where we met. We visited when we lived far apart and hung out like old friends when fate had us living in the same city. 

When I moved to California, we remained friends, talking on the phone now and again to catch up. 

One day, he told me he was struggling in his hometown and needed a fresh start. I invited him to stay with me in California – not to enter a relationship but to help him get back on his feet someplace new. 

At the time, I didn’t know the extent of his alcoholism, and neither of us knew he had bipolar disorder. 

Starting a Relationship

The chemistry we had when we first met never truly went away. Living together brought it back, and eventually, we decided to date. 

I cared about him so much, but now I realize he wasn’t the person I thought he was. 

I remembered the fun, carefree, ambitious young man I met as a freshman, and I thought a piece of that was still there. 

If it was, it was buried under layers of anger, self-loathing, and alcohol. 

But I didn’t see it. 

I had this image of him from those days built up in my head, and I refused to believe that awesome person was truly gone. When his behavior didn’t coincide with the image, I made excuses. 

My Biggest Financial Mistake: Investing in the Wrong Man

I lost thousands of dollars over the years. The entire five-year nightmare combines to form the worst financial mistake of my life. 

It started from day one. J didn’t work for the first few years we were together. I paid all the bills and all our living expenses. I even supported his beer habit. 

At first, I didn’t mind. I let him move in so he could start over, and I knew it would take some time. 

But as the months turned into years, he always had an excuse. The economy was terrible. There weren’t any jobs nearby. He couldn’t compete in the job market. 

A combination of naivety and not wanting to deal with it helped me believe his lies. He got away with leaching off me for years. 

Starting a Business

Eventually, I told him I’d no longer support his alcohol habit. He needed to make money. 

As the same excuses flowed through him, I put my foot down, but he devised a brilliant plan. 

He started a new business out of the garage, buying and selling video games. I could see the vision. He knew what sold and was great at scoping out deals, so I gave him some start-up money. 

He bought games at garage sales and off Craigslist, then resold them. However, he refused to sell on eBay. Instead, he sold to a reseller who sold on eBay because listing them himself was too much work. He missed thousands of dollars because he was too lazy to list things himself. 

Occasionally, he needed money for a deal. He’d beg and plead, guilt-trip me, and promise to pay me back with the profit (sometimes he did, but more often, he didn’t), and I always gave in. 

Usually, he had enough money to keep his small business afloat and keep himself in alcohol and cigarettes. He never paid a dime towards living expenses. 

Getting a Job

J eventually found a decent-paying job doing office work with our neighbor’s company. Our neighbor kindly drove him daily, but he had to be up by 5:30 to catch the ride. 

He worked from 6 am to 2 pm, and he was usually drunk by the time I got home. 

Sometimes, he wasn’t 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 glad I was no longer paying for his habit.

He’d Rather Drink than Work

One random day in 2016, he decided he’d rather stay home and drink than go to work. Before this, things weren’t good by any means, but I was holding things together. 

I couldn’t anymore. His decision to not work was a final straw. I told him I was done. 

The pleading began. 

He promised he’d do better, and I think he tried. He’d stay sober for a week, fall off the wagon, make it another few days, fall off again, and so on. It seemed like he did just enough to get me to stay. 

I finally had enough of the whirlwind and told him I’d only stay with him if he went to rehab. He agreed. 

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 for about 60 days. I was so proud of him. He became a team leader and helped others on their journey to discovery. He was ready to give up alcohol and rejoin the real world. 

I saw hints of the person I knew way back when; before alcohol destroyed him. I was ready to try again. 

After Rehab

Unfortunately, his newfound sobriety only lasted for four days. He made up some story about why drinking was ok because he held himself accountable and knew it was wrong.

For the next six months, we were very on-and-off. I’d break up with him, he’d claim to try again, I’d give him another chance, and then we’d be right back at square one. He made my life miserable when we were broken up, creating this unbearable tension that I couldn’t escape. When drunk, he’d threaten to sue me for whichever perceived injustice of the day. It was easier to stay with him than to break up and try to remove him from my home. 

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.

Throwing More Money Away

I helped him yet again, lending him two thousand dollars to get a top DUI lawyer.

By this point, he had siphoned about ten grand away from me, so I didn’t want to give him the money. I was tired of investing in him and losing. 

However, he promised to pay me back a month after receiving his tax refund check. He also absolutely needed the lawyer to resolve one last issue. 

His high-pressure sales tactics won. I lent it to him on the strict condition that he’d pay me back as soon as he got his check. 

He didn’t. 

He got the check and gave the money away to his friend, who was “in a bad situation.”

The camel’s back broke. I was truly defeated and lost any trust I ever had in him. Looking back, I see this was where our relationship ended, though I admit my final straw should have come much sooner. 

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. At this point, it wasn’t out of love or trust but of feeling responsible and fearful of both him and failure. I invested four years into him; it HAD to work, even if I hated him. It had to work because I was trapped with him, and my only hope for a happier life was for him to get better. 

When I got the transfer to Savannah, I told him 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!

But inside, I was dying. I thought about leaving him on the side of the road somewhere during our drive, but I couldn’t bring myself to treat another person so poorly despite how he’d treated me over the years. 

I hoped the move would be the catalyst he needed to change. 

The Nightmare Continues in Georgia

The first few months in Savannah were a nightmare. But, of course, I was to blame. It was my fault he had no friends, couldn’t find a job, and had no one in Savannah. 

It was my fault he turned to alcohol to ease these troubles.

I ended things with him again in October of 2017.  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 dating, 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 demanding tasks around the house to start paying me back. 

I was astonished. 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. 

One Final Giant Financial Mistake

I knew that there was one major thing limiting him in his newfound quest for independence. He couldn’t get around town. 

He was relying on either me or a less-than-reliable bus system. If he was going to make it, this was unsustainable.

So, I told him I would help him get a car for Christmas. I offered to pay $500-1000 for a down payment or 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. 

He threatened to do just that when I tried to break up with him. He used the financial disaster of the car as a way to keep me with him.  

It’s Over

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. 

The Mistake that Keeps On Giving

He rarely paid for the car, forcing me to take on the burden or risk my credit rating. He constantly used it to weasel his way back into my life. He even tried to get me to buy him a new one after he got into an accident. Eventually, I paid it off in full, so I wouldn’t have to worry about it anymore. 

Overall, I probably lost between 20 and 30 thousand dollars on him, between the car, his video games, the health care plan, alcohol, and his living expenses. I’d probably be financially independent by now if I had invested that money instead. 

Repeating the Same Patterns 

After he left for good, I immediately jumped into another relationship with a charismatic user. He said all the right things and acted like he truly loved me for me. I made the mistake of opening up to him early about the horrible trauma I had just endured, and he saw it as an invitation to do the same thing, only with a shiny veneer of acting like he loved me (which J rarely provided). 

He love-bombed me, acted like I was the only person on the planet, and used all that to move himself right into my home and wallet

I fell fast and right back into old patterns of supporting him while he blew money on everything else. 

He couldn’t keep up the act of caring about me for very long. The relationship lasted a little over a year, but I finally realized he didn’t even like me, and I broke up with him. 

I was devastated. I thought he was terrific and truly loved me, and learning it was all a manipulative act to use me destroyed the little self-confidence I had left after being with J. 

But I got through it and learned to love myself again. 


It’s been six years since the breakup, and the mistakes still haunt me. I’m humiliated that I let him use me for so long and that I jumped headfirst into a relationship with an even bigger user. 

However, I’ve also realized that it wasn’t all my fault. I was in an emotionally and financially abusive relationship. J used any tactic he could to keep me trapped with him. At times, I couldn’t see a way out. I was so beaten down, defeated, and depressed that I couldn’t even fight back. 

Part of it was also the sunk-cost fallacy. I didn’t want to lose my investment, so I threw more money at it, hoping it would improve. He knew that and used it against me, claiming he’d pay me back after this one goal, but the goalposts constantly shifted. 

Most of it was emotional abuse. He used high-pressure sales tactics, appealed to my empathy, and threatened to worsen things. He refused to leave when I broke up with him and went so far as to threaten legal action to ensure he’d be allowed to stay. 

He created a cloud of tension that was impossible to escape until he got what he wanted. 

I went into detail about the things he did in a cathartic eBook titled “This is Abuse,” so I won’t share them all again here. However, anyone who isn’t sure whether their relationship is abusive should give it a read. It covers both J and the next guy and showcases how insidious emotional and financial abuse can be. 

Abusers are clever, doing just enough that you feel trapped but not sufficient to cause any legal damage. It makes victims unsure of whether what’s happening is abuse or not. 

It is. 

Does this Sound Familiar?

I used to scoff at stories of abused women, wondering why they’d stay. J wasn’t even physically abusive, but I learned how strong an abusive man’s grasp can be.

What do you do when he won’t leave, especially if there’s no physical violence? You can spend thousands of dollars on eviction proceedings while living in misery, unsure of what he’ll do next, or you can agree to give him “one more chance” and live in a tolerable level of unhappiness. 

I get why women choose the latter. 

J only left for good after he put his hands on me in violence, and only because he knew I had something on him he couldn’t fight. He left that night and never returned, though he still tried to get under my skin about the car. 

For anyone in a similar situation, I understand why you’re staying and how hard it is to escape. 

I’m here for you. 

But if you can get out, do it. They won’t change. They will say whatever they think you want to hear, so they get to keep doing what they want. But it will all be empty promises with no follow-through. You deserve better than that. 

Escaping will be the hardest thing you’ve ever done, but I promise it’s worth it. 

If you need help, call the Domestic Abuse Hotline: 800-799-7233

If you’re unsure whether you’re in an abusive situation, call the hotline. Get the help you need to get out. 


Author: Melanie Allen

Title: Journalist

Expertise: Pursuing Your Passions, Travel, Wellness, Hobbies, Finance, Gaming, Happiness

Melanie Allen is an American journalist and happiness expert. She has bylines on MSN, the AP News Wire, Wealth of Geeks, Media Decision, and numerous media outlets across the nation and is a certified happiness life coach. She covers a wide range of topics centered around self-actualization and the quest for a fulfilling life. 

26 thoughts on “6 Years Later – Reflecting on the Biggest 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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