John D. Spooner is an investment adviser, author and novelist. His most recent book is No One Ever Told Us That: Money and Life Lessons for Young Adults. Here, he responds to queries from advice seekers of all ages. Send your conundrums to

I’m a single, millennial woman, and all I read about my generation is how entitled, lazy, misinformed and uninterested in anything from the past we are. I totally disagree, and it makes my friends and me furious. The biggest thing we do care about? Happiness. What’s so wrong with that? Well, there are now more millennials than any other cadre in the country, so we’d better pay attention to you. There are things about your generation that I’m jealous of and that I love. The thing I most love is your spirit of adventure, the sense of wanting it now, not deferring pleasure. This concept would be a sin to most of the older generations, but you’re not afraid to explore on the cheap. You created Airbnb and other apps to be your springboards to life. And I love that you may have 20 jobs in your lifetime, not simply one that used to lead to a gold watch after 30 years—you don’t even want a gold watch. I have young friends who are backpacking in Patagonia, sailing in French Polynesia and trekking in Nepal. And all of them are doing it inexpensively, embracing adventure and the world. Your worldview is not Somerville, Quincy, Worcester or Newton. It’s a global view. You are going to be better equipped to handle the bumps when they inevitably come because you’ve dared to see the world before you were 50.

I’m in my late 40s and I’m currently engaged to a great woman. The problem is, the whole wedding thing has me freaking out. First of all, it’s stupid expensive, and I don’t want to spend $50,000 or more on a wedding that is basically a party for a bunch of people I don’t even know, not to mention the dress, flowers, honeymoon, etc. We’ve been living together for six years. I just wish we could have a small quiet ceremony and then get on with our lives. She’s really into it, and I don’t want to disappoint her, but it’s making me sick. Who are we trying to impress? Is there a way to convince my fiancee that a big wedding at our age is a waste, or should I suck it up and stop complaining? The snarky side of me says, “If your prospective in-laws are paying for the wedding, go for it.” But I get it. Anything that smacks of “conventional” is long gone. In more than half of the weddings I’ve been to in the past two years, the ceremony was officiated by someone who got a license for a day to perform the ceremony: a great uncle of the groom, a famous drunk, an owner of a 45-foot catamaran that would take them away from the reception, the eighth-grade English teacher of the bride, and a friend of the bride who read her horoscope and claimed she was a witch.

But even if you two are going to pay for your own wedding—with no help from anyone—you should know this: If your fiancee wants an old-fashioned wedding, do it. If you elope, you’ll be setting yourself up for your new wife to eventually proclaim, “You knew I had my heart set on a big wedding!”

I think it’s a priceless experience, and you’ll make the money back eventually. You both will cherish the pictures and the memories. I’m snarky, but I’m a sucker for big weddings, too. Don’t forget the rice and the rose petals.

I live in a large condominium complex just west of Boston. We are allowed cats as pets, but not dogs. One handicapped unit owner was allowed a small comfort dog, and no one took issue with that. Recently, though, I’ve seen people coming and going with lots of dogs—large breeds at that. There are now several residents that are using comfort dogs as the reason they are permitted to keep the canines. Really. I had no idea there were so many emotionally challenged people out there. Should I try to have a vote taken and see how the majority of owners feel about it? We can always add a “no dogs” rule to the bylaws, but I worry I’m making a mountain out of a molehill. Well, if I’ve ever heard a no-win situation, this is it. I have a great friend who is fond of saying—in all kinds of situations—“Either way, I’m screwed.” With 325 million Americans, for everything you love, there are endless people who will hate it. I live in a building that allows both cats and dogs and everyone is well-behaved, even the owners. A condo or co-op board can issue any rules it wants. But it’s very tough to adjudicate “comfort” anything, and discrimination between dog and cat lovers can lead to confrontation, even lawsuits. In my opinion, your board should either say, “no pets at all,” or “anything goes.”

But are you really surprised that there are “so many emotionally challenged people out there?” Almost everyone I know is emotionally challenged. My comfort creatures are…books. 

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