Dear Blake,

I have two sons, 18 and 20. Since they were young, whenever we invited one of their friends to join us for an activity, dinner, etc., I have treated that friend. Over the past few years, we have included one friend in more activities as well as on numerous family vacations.

The problem is, the more we have treated this friend, the more he has expected. For example, during our last weeklong vacation, he expected us to pay not only for every meal, but also every little incidental. When he was once asked for $10 by a vendor, he immediately complained. (It was for a short safety class so he could jet ski as our guest.)

Before he was 18, his parents sent money to help cover expenses, but now I cover it all. This would be a lot easier to accept if he even once said “thank you” or seemed appreciative. Aside from this, he’s a pleasant, respectful 19-year-old who has been my sons’ friend for almost 10 years.

Should I say something to him? Should I ask if he enjoys our trips and activities and if he can cover some of his own expenses? It is easily financially feasible. I don’t want to risk my sons’ friendship, but I feel the situation has gotten out of hand.

Signed, Glenda
From, Boston Massachusetts

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Dear Glenda,

I agree with you regarding your sons’ ungrateful friend. Obviously you have to do something drastic to prevent this young man from reaching his subconscious goal of becoming a homeless bum. Here are some ideas. Have your sons ask his parents if they can go on a vacation with them, all expenses paid. When they emphatically tell them “no” and why, use that exact same logic on their worthless lazy buddy. Tell your sons that you’re going to start using a large portion of the money you planned on spending on them, and spend it on their friend during the outings and vacation. At that point, your sons will immediately demand that their friend start paying his fair share… after they beat him up. Or, tell their friend he can still come along, but for every activity he must give you at least ten verifiable job applications that he filled out. And once he starts working, he won’t have time to sponge of you anymore. And lastly, try this. Have him show up about 5 or 6 hours before they time you plan to leave, and assign him chores. Tell him that your family won’t leave until he has completed the tasks at a level of your satisfaction. When he becomes so tired and about to collapse, tell him to take a quick nap. When he wakes up, have him laying outside your front door, and leave a note in his hand promising to send him a post card… postage due. I hope this helps.