Today's 98.3 TRY Social Dilemma came from Jeremy and it's about housesitting. Here's his email: Hi Jaime. Here's my issue. I had to leave on business for a couple of weeks and paid a local college-aged guy in the neighborhood a few hundred bucks to stay at my house and watch over the place. He was allowed to stay over, eat whatever he wanted, and was given free reign and trust. When I came back, however, I noticed that the couch I’d just paid over three-grand for had some major stain damage. Now, I’m wondering if it’s appropriate to bill him for cleaning it. It’s a light-colored fabric, and now it’s loaded with what looks like Cheeto dust, condiments, and fingerprint dirt. Any thoughts on this from anyone? Thanks ~ Jeremy. This is a tough one. I've had people housesit my home before. Sometimes you come home and your house is cleaner than when you left, and sometimes you come home and it's a mess. I feel like it's part of the deal when you have a housesitter. Unfortunately, I don't think there's much Jeremy can do. But that's just my take. Hopefully you have better advice. Let's help him out at the TRY Facebook page.