Dear Mr. Schaeffer:
I recently suffered a humiliating embarrassment, but with your help, it just might turn out to have a silver lining. I’m one of the older lawyers at my law firm—72, to be exact—but I’m still sharp as a tack. Even so, I emerged last week from the men’s room on the 57th floor with a “toilet paper streamer” hanging from the waist of my slacks. At my age, you’ve got to laugh at life's little challenges, but I must admit, it wasn’t easy in this case. As I learned later, the streamer went all the way to the floor, and it stayed there most of the afternoon, much to the amusement of the firm’s junior associates. I had no idea they were laughing at me, thinking their amusement had more to do with the old jokes I love to share with them, which I learned as a boy when I’d go to vaudeville shows with my father.
Anyway, to get on with my story, my father passed away long ago, as did my wife, God rest her soul. Whenever I think about slowing down, I realize how lonely I’d be cooped up at home each day all by myself. I don’t want that. But I’m digressing and I apologize. I’ll move on to the silver lining. At about three in the afternoon on the day of my embarrassing incident, one of our cute young secretaries, whom I’ll call “Susan,” tapped me on the shoulder and discretely informed me of my predicament, i.e., she whispered to me about the toilet paper. I realize that by all things right and proper, I should have been incredibly embarrassed by what had happened, but I was so taken by Susan’s blue eyes, long eyelashes, and blonde hair, not to mention how good she smelled so close to my face, that I retrieved the streamer, balled it up, and disposed of it in the trash receptacle without even blushing.
Much to my amusement, however, Susan was blushing—she must have realized that I’ve long had my eye on her! To learn that my infatuation for Susan was being returned was quite a pleasant development in my life, let me tell you, even if it did come at the expense of one hell of an embarrassing situation. But it’s caused another small problem. As a token of my appreciation for what Susan did for me, I want to present her with a gift—something containing some gold, I think, as well as some small diamonds. Having had lots of experience buying jewelry for my wife, God rest her soul, I can handle this part of my task, but about the rest of it, I’m a little uncertain. Here’s my conundrum. When I present the gift to Susan, I also want to ask her out to dinner. But I’m not sure what to say.
I’ve heard, Mr. Schaeffer, that you know a thing or two about connecting with the younger generation. Even though Susan’s only 26, I’d really like her to be my new companion. Just thinking of the surprise the members of my Tuesday lunch club will display when I introduce her to them is making me tremble with anticipation. Do you think you can help?
Signed, Love-Struck in Lower Manhattan
I’m flattered you would ask me for advice, although the problem of how to romance a secretary is a very tricky one, fraught with peril and dangerous to talk about even behind closed doors. As you surmised, however, I do know a thing or two about the younger generation, which gives me an idea. Have you ever heard of Donald Trump? He’s an old man very much like yourself. Even so, he’s had tremendous success persuading extremely young women to gather around him like moths gather around a flame. And if I’m right, it just might be possible for you to duplicate his success.
What I suggest is that you forget the jewelry altogether. You’ll also need to expand your horizons just a bit by focusing your attentions not only on the beautiful and fresh-smelling Susan, but also the fifteen other most beautiful secretaries at your firm. Tell them they’re each going to receive a special invitation to accompany you to dinner, not once but several times, where you’ll “interview” them to be your secretary. The winner will get both the satisfaction of having beaten out all the others for the job, and the knowledge that she will have you all to herself until you die unexpectedly, lose your temper and fire her, or suffer a strategic bankruptcy.
Will they bite? They just might. But to make absolutely certain that they’ll not only agree to your offer, but will also do absolutely anything you ask—and I mean anything, if you get my drift—all you have to do is hire a videographer to follow you and the secretaries around wherever you go. Don’t worry about objections that you’ll be rudely depriving the young women of their privacy. They won’t care! To test this thesis, simply tell them you’re going to broadcast the videographer’s footage in Times Square during lunch hour, and watch how they all squeal with delight. It will truly be something to behold.
If things go right for you, it’s going to be a very wild ride indeed. Just be sure to comb your hair forward into a single gigantic greasy mound, brag outrageously about your accomplishments both major and minor at every opportunity, and always keep your front to the camera after you’ve just emerged from a restroom. And good luck!
Your friend, Evan Schaeffer
1. Advice to Law Firm Partners #3 (More About Connecting with the Younger Generation)
2. The "Advice" Category--all previous advice posts