My roommate stole from me

Dear Cary,

My roommate and I have been good friends ever since our freshman year in college, eventually finding ourselves in the same city and moving in as roommates. For the most part, he's a good roommate -- clean, funny and considerate -- and a lot of fun to be around. However, I've always known him to be a bit of a cheapskate and a kleptomaniac. When we lived together in college, he would routinely steal from the campus bookstore (nothing too expensive) and supplied our house with toilet paper that he jacked from the public bathroom next to his lab.

Since moving in together, his sense of morality has loosened. He stole two bikes off racks, one for him and one for his girlfriend, and has bragged about putting his residency elsewhere in order to pay less of a tax rate. For the most part, this didn't bug me because his theft didn't affect me. After all, I benefited from all the toilet paper and pens and light bulbs that he lifted.

The problem is that I recently found that he has been stealing from me. Last December, my iPod Shuffle that I use when running went missing. I initially believed that I may have misplaced it when I moved around the furniture in my room to accommodate a new desktop, but I figured that it was getting cold out, the iPod would be of no use since I didn't plan on running in chilly weather either. Surely it would turn up later.

But now that sunny skies are here, I'm eager to get back into the habit. Yesterday morning, I emailed him to see if he knew of anything that may have happened to the iPod, and he said that he didn't recall seeing it since then. Now, I have never lost a hand-held electronic device in my life, and I'm quick to immediately charge the iPod because I'm very OCD about what songs are on it. I knew it would be extremely unlikely for me to misplace it. Thus, I concluded he must be full of shit.

Because we're buds, he has a hookah that I would sometimes borrow to smoke and watch television. One time he was angry that I had not cleaned it out, and a few days later the hookah mysteriously vanished from our apartment. He denied hiding it, but I had my suspicions. These were later confirmed months later when he brought it out for a party and sheepishly admitted he had lied to me and kept it under his bed.

Now I would never violate his privacy, but considering this precedent, an exception had to be made. I went into his room yesterday morning and found an iPod shuffle of the same color and design sitting with a pair of headphones that also matched the exact type I was missing hidden in a drawer next to his desk. I hooked the iPod up to my computer and found that he had cleared out all of my songs and renamed the iPod after himself. If there was any doubt that he may have mysteriously purchased the exact same model as me and kept it a secret, a look-up of the iPod's registration matched the day I purchased it from the Apple store. Furthermore, the earliest songs on the iPod were loaded in early January, just weeks after it went missing. After confirming the evidence (and taking a few pictures of it for good measure) I put the iPod back into his desk and I now remain at a loss for what to do next.

What's more is that our lease is ending in just over a week, so we will no longer be roommates, which adds tension to the situation. In fact, he's asked our close group of friends to help him move to his new apartment. I'm upset that he lied to an old friend and I know for a fact he would have moved on to the new apartment having no intentions to ever return what he stole. Our group of friends are scheduled to go on a camping trip this weekend, and conveniently enough, I also won a pair of concert tickets yesterday, which I used as an excuse to back out on getting drunk in the woods. While it's serendipitous that I won these tickets (I do want to go to this show), I would have certainly looked for another reason to avoid spending my weekend with him now that I know he's a thief.

I'm furious about the whole situation. I first thought about simply taking the iPod back without telling him, but now he is aware that I'm currently looking for it, he would know I was snooping through his stuff. I clearly want my iPod back, and I'd like to retrieve it with a minimal amount of pain. But while I'm normally a drama-free person, there is also a part of me that wants to publicly humiliate him in front of our friends for being an assbag for stooping so low to steal a $50 iPod from a person whose salary is a third of his own. My question for you is what should I do?

Lost in the Shuffle

Dear Lost,

You call your friend a kleptomaniac. It's possible that he really is one. Kleptomania is a serious mental disorder. People who have it cannot control their impulses to steal things. Please take a look at the Mayo Clinic site linked to above and consider the possibility that if he is a kleptomaniac, then he is not really an assbag. He's a guy who needs your help.

Then confront him privately, as a friend -- a friend who is angry with him, for sure, but still, as a friend. Tell him that you believe he took your iPod and that this made you angry, but you understand that he may be suffering from kleptomania, which is a mental disorder. Also tell him that it's no secret he has been taking things for a long time.

It's nothing to be ashamed of. It's something that can be treated. Give him a chance to come clean. Tell him it would make you happy if he would give you back the iPod but the more important thing is that he get help. He may tell you he doesn't have it anymore, or that he never stole it, that you're crazy to think such a thing, that you're a bad friend. He may say all kinds of things. Give him time. Don't argue or fight with him. Just tell him that you've been friends a long time, that you care about him, that you think he may have a problem, and that you want to see him call his doctor and ask for a referral to a specialist.

If you are persistent, maybe he will admit it. Maybe he will agree to call his doctor and ask for help.

Now, kleptomania is rare. Not everyone who takes your stuff is a kleptomaniac. Criminals suffer from a wide range of mental health problems,  from schizophrenia to addiction to various impulse control issues --  of which kleptomania is one type. But not all criminals have mental problems, nor do their diagnoses absolve them of responsibility.

It's possible that your roommate is not a kleptomaniac. He may just be a person who steals things and lies about it. It may turn out that it's a simple case of if you hang out with a thief, sooner or later you're going to get robbed.

But I suggest you take the high road. Give him a chance to talk honestly about something that may have been troubling him for years. By taking the high road, you can preserve your reputation among your friends. What I mean is, if you were to go in and take the iPod, which it's very tempting to do, it's possible he would spread the word that you are a thief. It would be hard to deny that you took it, and hard to explain that he took it from you. And if you start calling him a thief to others, it may sound like calumny.

So ask for the iPod back, and offer your support to him if he is willing to admit that he may have a problem. But be prepared to be rebuffed, to lose your iPod and your friendship. You may have to let it go. There are more important things at stake here.

What? You want more advice?

• Read more Cary Tennis in the Since You Asked directory.
• See what others are saying and/or join the conversation in the Table Talk forum.
• Ask for advice. Letter writers: Please think carefully! By sending a letter to advice@salon.com, you are giving Salon permission to publish it. Once you submit it, it may not be possible to rescind it. So be sure. If you are not sure, sleep on it. You can always send tomorrow. Ready? OK, Submit your letter for publication.
• Or, just make a comment to Cary Tennis not for publication.
• Or, send a letter to Salon's editors not for publication.