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How to Deal With Freeloading Moochers

From Our Mailbag:

Hi Dr. Kim,

I read with interest your article on Jason and people like him who frequently take advantage of others. I've been struggling with this very issue for several years, wanting to be helpful to a friend and wanting to see the best in him, but with passage of time and countless disheartening "favors" I've realized that this person will not stop taking advantage of me until I put an end to it.

The problem is that I don't know how to end it without making things awkward. We have mutual contacts and I have a feeling that he will twist whatever I have to say in a way that makes me look like the bad person and him the victim - this has been his pattern of behavior all these years I have known him.

It makes me sad to see him repeatedly taking advantage of people around him. I've tried to distance myself but he continues to ask to hang out. Do you have any suggestions on how to handle this type of situation? I would really appreciate your guidance.


Sam P.


Dear Sam,

I feel for the angst that you have experienced over this fellow - I am intimately aware of what it's like to want to be a generous and thoughtful friend, only to realize that a person you have given your heart, time, and resources to has no qualms about repeatedly taking advantage of your kindness.

I've come to believe that there is a type of person in this world who has grown up to feel there is nothing wrong with regularly asking others for favors and using other people's resources. Let's arbitrarily call this type of person Reggie for the purpose of coming to terms with how to view and deal with the Reggies of the world.

My feeling is that Reggies don't see their actions as taking advantage; rather, they see themselves as grinding, hustling, doing whatever it takes to get what they want for themselves and their loved ones. When they are able to score a free stay at your home or in your hotel room, when they're able to get you to pay for their meal or have dinner at your place, Reggies experience a sense of satisfaction, feeling that their hard work - smooth talking and persuasive storytelling - has led to a well deserved reward.

It doesn't occur to Reggies that in using your hard-earned resources, they are taking away from you or your loved ones. All they zoom in on are benefits they reap for free.

Sophisticated Reggies strive to create the illusion that they aren't taking advantage. They are experts in making half-hearted disingenuous offers to "chip in" or to "get the next one." They are good at saying thank you and proclaiming what a good friend you are, how you are just like family, all while looking ahead to other ways they can use you - always working, always hustling.

I owe you one.

I'll pay you back.

You're the best.

You're such a good friend.

You my homie.

None of these words cost Reggies a thing. These phrases are purposefully used with hope they can avoid looking like the freeloading moochers they are.

My experience has been that most Reggies don't intend to hurt their prey. When Reggies bring themselves and their friends to sleep over and eat your food, they aren't thinking of the time and work that you put in to afford your place and edibles; they are only celebrating their win. As they over-fill their cereal bowl with almond milk that you earned with honest work, they think nothing of leaving most of the milk to be discarded - why should they be careful with your resources when they are #winning?

I don't mean to patronize with my description of the Reggies of our world and their mindset. My hope is to clearly illuminate said mindset so that kind-hearted Sam and others like him can more easily stand up and peacefully say no without guilt or a need to explain why not. When we understand how Reggies think and how they view others, it liberates us to better honour our efforts, hard-earned resources, and those in our lives who are more deserving of our love and support.

Is it fruitful to respectfully express to Reggies that we feel they are taking advantage?

In my experience, Reggies do not have the mental or emotional capacity to consider the possibility that they are living selfishly. My feeling is that if Reggies could consider this possibility, they wouldn't take advantage of others to begin with.

By telling Reggies that we will no longer let them take advantage of us, the most likely outcome is some blend of indignation, hostility, and masterful storytelling to others where we become the character who has wronged Reggie, so who else will now step up to help Reggie out?

My opinion is that there is little potential good that can come from telling folks like Reggie that we feel they are selfish. The only people who stand a chance of having some impact with this level of feedback on character and values are blood family members, mostly parents and grandparents. But even then, full grown adult Reggies typically do not possess minds or hearts that are ripe for personal growth and transformation, so sharing such feedback usually doesn't end well.

Sam: If you are still feeling conflicted about peacefully moving on from your Reggie's selfish ways, it might be helpful to ask yourself if you wish such a friend for a loved one - for your child, brother, grandmother, sister? If the answer is a resounding NO THANK YOU, on behalf of our readership, I hereby grant you permission to send him light and send him off. How to do this, you ask? Simply don't engage. And when Reggie asks you what's wrong, say nothing is wrong, I wish you well.

Sending you my best,

Ben Kim

P.S. In case it's helpful, here's the Philly version of my reply:


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Sometimes the Reggies of this world are family members, and it is important to realize that despite what they say, you are NOT helping them. Even if they twist and claim victim status, you and your true friends will know the truth. It is very hard but we do have to develop a thicker skin. I am experiencing this now too, and it is hard to keep my boundaries, but it is necessary. No one else will take care of me until I do first.

I appreciate you sharing, and I love your point about us not helping the Reggies of the world by enabling such behaviour. We only cripple them further, as with such a mindset, they will find it difficult to earn the respect and trust of those around them.

I really appreciated this article. I had a Reggie that I had to gently let go of, with well wishes. Your article helped me feel better about what I felt I had to do, for myself.

I'm thankful that you connected with this, Linda. We are never alone in our life experiences. It's wonderful that you were able to take a gentle approach to letting your Reggie go. I hope you take comfort in knowing that you did not fortify such behaviour and thus did not cripple your Reggie further.

Oh, yes, Dr. Kim. I've had more than my share of the moochers, some of them family members as well. They always take and never reciprocate. Decided one day I was doing this to myself because I was ignoring that small inner voice that said not to trust or rely on this person, or my boundaries were being violated. I learned the hard way to trust my inner voice. I believe the best way to satisfy the part of us that desires to give and be generous is to give freely to well-deserved charities and organizations that are promoting good works and causes we are in harmony with in this world and leave any rewards if at all to come directly from a Divine Universe, who will always out give us. In this regard, aligning ourselves and our personal resources with a Divine source, we can never feel lonely, no matter how many human beings we must release from our lives - including family. Peace.

Cheryl, thank you so much for your empathy, and for sharing your approach to finding peace in such circumstances. I especially love the following thought:

"Decided one day I was doing this to myself because I was ignoring that small inner voice that said not to trust or rely on this person, or my boundaries were being violated. I learned the hard way to trust my inner voice."

I agreed with every word you wrote, Dr. Kim, and was reminded of a friend my husband had from boyhood. Total Reggie type. It grated on my nerves; my husband and another childhood friend of his I'll call Archie seemed resigned to accepting the selfish behaviour.

We all went out to a restaurant, and true to form, Reggie ordered the most expensive cocktail, appetizer, and main course on the menu. I had never once witnessed Reggie pay for his meals, although he would boast about how much money he had in his savings account nearly every time.

I needed to use the washroom, and on my way there, I saw our waitress. I asked her if it weren't too much trouble, if she could give us separate checks. She nodded, said she wondered if we'd want separate tabs, and the way she said it indicated to me she'd seen other Reggies.

We had a lovely meal, and when it came time to settle up, the waitress appeared saying sweetly, "I took it upon myself to give you separate checks," and swiftly passed out three tabs, one for my husband and me, and one each to my husband's friends.

Reggie blanched. Archie thanked the waitress, as did I. Reggie's bill was almost the same amount that mine and my husband's was. He couldn't very well say he had no money, as he had once again broadcast rather loudly how much money he had in his savings account.

My husband and I tend to tip well since we'd had restaurant jobs in the past, and I tipped extra. So did Archie. I'm not sure what Reggie tipped; he did complain about the prices, but he had seen the prices on the menu as much as we had, and it was obvious to us three that he only cared about the cost when he had to pay.

We've been out to eat with Archie many, many times since. Sometimes he picks up the tab, sometimes we do, sometimes we split it. Reggie wasn't keen on meeting up with us after that. I guess for him it was game over.

Thank you for sharing, Megan. I know how liberating it is to move on from feeding entitlement syndrome in those who actively seek to take advantage of others. I'm glad for you and your husband, as well as Archie. The Reggies of the world deepen our appreciation of the Archies, don't they? :)