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 thedance@improper.com

I work in an office where most of my coworkers are a lot younger than me. On occasion, we grab drinks after work. It’s a lot of fun, but I’m constantly getting teased for my seniority. I recently tried to cover up some of my gray hairs, but it ended in total embarrassment. I feel like I’m becoming somewhat of a joke to them. I really wish there were men my age that I could relate to, but I still want to be friendly with my coworkers. What should I do? 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.

My friend runs an event-planning business and keeps promising to invite me to some of the high-profile events he plans. I can’t tell if he’s blowing me off, but I have yet to get an invite, though he insists it just keeps slipping his mind. How can I get into one of these events without being too overbearing on my friend? 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.

Recently, I started seeing a guy I met at a concert. We started talking, and he told me that he is in his own band. I was impressed, and we started dating soon after. However, my friends to whom I have introduced him think that he is a complete burnout and lacks ambition, but I find him fun and exciting. Even my mother is worried about me now because he’s not on a traditional career path. Should I heed their advice or go with my heart? 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.

I started a great new job recently and made a big move from the suburbs to the city. One of my coworkers and I have begun spending more time together during work. He will come over to my desk and chat with me, but nothing beyond that. However, yesterday, he asked me if I wanted to grab coffee with him before work. I don’t want an office fling to distract me from my new job, but I am interested in him. Even worse, I cannot tell if this is a date or just a friendly gesture. What is the proper etiquette in this situation? 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.