This Guy Hits Me Up for Cash Quite Often

By Dr. Robert Wallace

September 19, 2025 5 min read

DR. WALLACE: The school year has just started, and already one of my friends is asking to borrow small quantities of money from me one or two days a week.

It's not a lot of money, but what bothers me is that he did the same thing toward the end of the last school year, and he never paid me back a dime the entire summer. I know exactly to the nickel how much I gave him last year. I can afford to supply him a little bit of money here and there, but that's not the point. I feel he's taking advantage of me, so what should I do? — It's a One-Way Street, via email

IT'S A ONE-WAY STREET: Your letter didn't mention your friend situation, so I'll preface my reply by saying that if he's truly from a home that doesn't have money, he may be embarrassed to ask you for this money, but he does so because he needs to buy food with it at school or something along those lines. So my first bit of advice is to find out what he's using the money for. Think back to the end of last year, and see if you can recall what he's doing with the money. Also evaluate his family situation to see if there are socioeconomic pressures that are causing him to do this.

If he comes from a family that provides him with a lunch from home or enough money to buy lunch at school, and he's dressed appropriately in reasonable clothes, then he may indeed be taking advantage of you for some reason. Perhaps you could ask him casually, in a moderate tone of voice (not accusatory), and find out directly what he's using the money for. Once you know that, you can make your own decision as to whether or not you want to keep floating small amounts of money his way.

If he happens to come up with a reasonable explanation, but he still possesses no direct way of repaying you, perhaps you could "hire" him to help you with anything reasonable, and ethical, you may need help with. I'm not talking about doing your homework here or buying you alcohol or anything illegal like that. An example would be: If you have a flat tire on your bicycle, he could walk it down to the local service station to get the air refilled for you. There may be a way that you could both benefit from this if you deem his reason for requiring the money to be appropriate.

HE WAS COOL THIS SUMMER, BUT NOW I FEEL SMOTHERED!

DR. WALLACE: I met an interesting guy who goes to our high school near the end of summer. We dated a few times on and off over the final weeks of the summertime, but now that we are back on our high school campus, he is literally all over me like a bear on a honeypot!

He's tracking me down all the hallways and trying to intercept me when I come out of every classroom, plus he always wants to eat lunch with me every single day. I have several girlfriends that I enjoyed eating lunch with on Tuesdays and Thursdays, and I'm not about to change that schedule for anyone.

He has a lot of positive qualities, but now I'm starting to doubt him because he's literally overbearing and smothering me to the point where I feel uncomfortable. How can I get things to go back to the way they were this summer? By this I mean, I wouldn't mind dating him perhaps once a week, but I don't want to be in touch with him every single day at this point in my life. — He's Suddenly a Bit Much, via email

HE'S SUDDENLY A BIT MUCH: My gut instinct tells me that what you're seeing now is closer to his core personality than what you experienced during those fleeting meetings toward the end of the summer.

You could perhaps tell him one time that you need your space at school, and that the two of you have only dated a few times, which means you're not an exclusive couple.

It may be possible to get him to calm down and casually date you once a week, or perhaps twice a month, but I feel he has already tipped his hand and that you'll end up being disappointed. Why? Because you've already seen his overbearing possessiveness up close.

Dr. Robert Wallace welcomes questions from readers. Although he is unable to reply to all of them individually, he will answer as many as possible in this column. Email him at [email protected]. To find out more about Dr. Robert Wallace and read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at www.creators.com.

Photo credit: Jp Valery at Unsplash

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