The New-Economy Mooch
So you have this friend you want to help out because she was one of the first casualties in the Great Recession. You picked up the tab for dinner one weekend. And the next. And the next. And then, hooray!—you're taking her out for drinks to celebrate her new job. And...picking up the bill. And the one after that. If you're starting to feel taken advantage of, you need to stop playing the fairy godmother game. Think of it this way: The next time you get together, you've got something to celebrate—that she's now capable of paying her own way. So when the bill comes and she starts studying her phone, try this one: "How great that we can go back to normal and split the check?!"
The Semi-Okay Accountant
There comes a time in every adult's life when she realizes the family friend who's been doing her taxes since she started working, while a lovely person, has never been able to get her any money back (or seems to get a suspiciously high refund). Or when she realizes her accountant is someone—come to think of it—she's never actually met. These are signs that it's time to start looking for someone new, someone with whom you can sit down and hash it all out. Finding a trustworthy, affordable CPA might not be the sexiest task in the world, but once you say goodbye to the wrong accountant and sign on with the right one, a stress you never knew you were carrying will float away. Especially—trust me here—if you are a consultant or a freelancer.
The "Expensive but Worth It"–Purchase Pusher
She's the most fun person to go shopping with. In fact, she's the only person to go shopping with: The purchase pusher. "Get it!" she urges when you're waffling over that obviously unnecessary dress/bag/pair of shoes/jadeite-green moped. "You deserve it!" Or, even worse, she insists (in words that turn your new accountant's spine to ice): "Sure it's expensive, but it's worth it!" She's right. The Italian-marble countertop is expensive because it's gorgeous. So is that first-edition copy of Franny and Zooey. So is a Ferrari. But just because something is beautiful doesn't mean you need to have it. And just because you deserve something doesn't mean (sorry) you can afford it.
The Aspiring Etsy Impresario
There are two kinds of people in most of our lives: those who have always secretly wanted to become yoga teachers, and those who have always secretly wanted to make and sell their own jewelry/beauty products/cute crafts. Let's make this clear: You're happy for your friend/family member, of course you are. You wish her all the best. But it may just be that glittery shoulder-brushing feather earrings at $40 a pop are not your deal, and because you're not her mother, you don't have to feel obligated to buy them and then wear them whenever you see her. (Unless you are her mother. In that case, you probably actually do.) That's not to say you don't want to support her in some way. Here's a line to memorize for use in such situations: "I am so glad you are making these! I'm going to spread the word to everyone I know." Then you can post a link to her site on your Facebook page and...you're done.
Santa Claus (or Other Fiscal Hero)
We've all had that moment of putting drinks—or an iPad or a jadeite-green moped—on a credit card and crossing our fingers that someone will arrive and make the balance disappear. Christmas miracles make for good cinema but weak financial planning. Same goes for timely arrivals of a generous Prince Charming or a heretofore-unknown rich relative (on his deathbed, in need of an heir). Alas, neither they nor Santa is going to appear and pay your credit card bills. Even if you're really, really good.
The Post-Cash Futurist
He's an early adapter. He had the first cell phone you ever saw—so what if it was the size of a baguette. He was on Friendster when you weren't sure what the Internet was. So of course your futuristic friend lives in a post-cash society and pays for everything with one of those nifty apps on his smarter-than-you-phone. But even though it's possible to buy a 99-cent ChapStick with a credit card, there are still places that take only cash, and you somehow always end up there, with him. He'll pay you back, just as soon as he gets some cash. Which will be never. You don't have to be the enabler with the wallet full of old-timey paper money. Just offer to walk with him to the nearest ATM.
The Bride with the 18-Month-Long Wedding
[Cue: curly elaborate gold script]: Save the date! You're invited to our engagement party...and bridal shower...and bachelorette party...and wedding-party weekend festivities...and our destination wedding in Aruba!...and then there will probably be a baby shower eventually...and...[End: curly gold script]...
When the very sight of yet another letterpress invitation fills your once-wedding-loving heart with dread, you've got an 18-month-long-bride in your life. Remember those days when a friend getting married meant you picked up a mixing bowl at Crate & Barrel and a few months later had a nice chicken dish while the DJ played "At Last"? What with the infestation of events and the expansion of bridal parties lately—not to mention the showers thrown by the bridesmaid and the other bridesmaid and the maid of honor and the other maid of honor—weddings have become the friendship equivalent of Ironman triathlons. But you can skip the minibus-with-the-stripper-pole party without putting a damper on the bridal bliss. If you're on the hook for six gift-giving events, consider coordinating with five friends, so that you can all go in together (and, essentially, each just buy one gift). Also, being a bridesmaid is going to mean even more events and investments (those traveling stripper poles don't pay for themselves, you know), so you might just want to deal tell the bride that you love her dearly but would rather attend as a civilian. Make it up to her with a special brunch, just the two of you—at a place where they serve unlimited mimosas, if at all possible.
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