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

 You have something few of your younger friends have—years of experience—and you can do everyone a favor by turning your age into an advantage. There’s a reason the very first chapter in my new book is called “Take the Pro to Lunch.” Counseling so many millennials, I find that they love stories of the past that reveal how business was done before the last five years. The stories you tell should teach lessons about the mistakes you made, the bosses you had, the business tips that can serve them well. If you tell these tales with a sense of humor, in a self-deprecating, not preachy way, your young friends may look at you more positively. And they may take some of the wisdom that you earned the hard way, particularly because you’re not their parent.

 The very best way to get his attention and make sure you’re on the invitation list is to buy yourself some personal notecards. Then you write your friend and say something simple like “I’m so looking forward to the kind of parties you’ve described to me.” He can ignore emails and texts, even phone conversations. But he can’t ignore a handwritten note on lovely stationery. His guilt level spikes. Then, you either get a bunch of invitations, or you get a new friend. And you’ll have fine stationery as ammunition for the next friend you want to put to the test.

 Well, in my view, you’re going with a lot more than your heart in this deal. “Fun and exciting” are things worth experiencing, particularly when you’re young. You should also know that there are people in your life who do not want you to have “fun and exciting” for all kinds of reasons. Some of them might wish that they had it.

But I’ll let you in on a little secret that perhaps you might know by now: Musicians are bad bets for long-term relationships. So are most creative people—actors, writers, painters. Those professions are often too tough to conquer… and the participants may be way too invested in their own dreams to take care of you in the ways you want to be cared about.

So enjoy the fling, or the romance. You can always lead with your heart. As long as you end up relying on your brain more than anything else.

 It’s not quite a friendly gesture, and it isn’t a date. So treat it as a “friendly gesture,” but know that your coworker likely is interested in you. Coffee will make it easy to find out about his status: single, or married, or “other.”

As an insecure person, I personally hate the idea of coffee. Intentions are clearer over cocktails and dinner, and there’s no pressure to rush back to work. As for the concept of an office fling, in my many years of observing work-time romance, I’ve found it is almost always a terrible idea. A short-term affair isn’t worth the trouble.


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