Almost every social group has a friend who is, shall we say, lacking in street smarts. You know, the type of friend who will believe you if you say, “Hey, did you hear ‘gullible’ isn’t listed in the dictionary?” They’re also the type of friend who will buy a “designer watch” from a street seller, then watch in horror as it falls apart thirty minutes later, right around the time they’re bragging about what a good deal they got on it.

As the saying goes, there’s no such thing as a free lunch, and there’s usually no such thing as a cheap designer watch. There’s a happy medium, though, between believing that every good deal is legitimate and believing that every good deal is a scam. Not everyone is out to get you, but you shouldn’t take everything at face value either.

Big-Ticket Scams

By now, we’ve all heard of the “Nigerian prince” scam, the one where someone sends you an email claiming that a Nigerian prince needs your help rescuing someone from prison or abduction or a bad hair day. The exact circumstances vary, but the person writing the email always needs your money to help them get to their money. If you do, then they’ll share the wealth. It’s so ridiculous that it’s amazing anyone ever fell for it, but people still do.

Not every scam is that blatant. Take a look at Craigslist, for instance. There are plenty of people selling genuine items in good faith, but there are others who list cars for prices way below market value, hoping someone will take the bait. Once you do, they’ll send you a check for a “delivery fee,” hoping you’ll cash the check and give the “fee” to a designated third party. A few days later, once the check bounces, you’ll be left holding the bag, with no car and a majorly overdrafted bank account.

Rather than navigate the sea of scammers on sites like Craigslist, go to a real live car dealership, one with employees who sell vehicles out of an actual building. You’ll have the security of knowing the dealership has been authorized by the car manufacturer to sell Fords, Chevys, Kias, etc. If a dealership goes out of bounds, they’ll have to answer to corporate.

Transparency Matters

It’s one thing if someone sells you a piece of artwork that they claim is an original Van Gogh. Unless this person is representing a very high-end auction house, they are not selling you a Van Gogh; they are selling you a cheap, garish reproduction.

But not all reproductions are garish and cheap. There’s a big market for people who want to buy designer things but know that they aren’t actually getting the real thing. If the buyer knows what they’re getting into because the seller freely admits that they aren’t selling originals, then that’s not a bad start.

Think about those drugstore perfumes that bill themselves as “Inspired by (Designer Fragrance).” It won’t smell exactly like the $100 department store fragrance, but it can get pretty close. Not everyone wants the real thing. Some people just want to feel like they did.

So since none of us are likely to be buying the original Mona Lisa anytime soon, look for places that offer quality reproductions of high-end art. You can have Monet without giving up all your money. You can appreciate the work of Van Gogh without giving up all your Van Dough.

So be skeptical, but not too skeptical. Be open to new experiences, but not too open. It’s a tricky balance, but with enough time and practice, you’ll be able to tell a truly great deal from one that just looks good on the surface.