Dear Spinsters,
I keep having really weird sex dreams about my boss, and now every time we’re in a meeting I’m afraid I’m going to slip and say something stupid. What should I do? I keep thinking of him naked! Is it okay to drop a few hints and pursue this? I’m in my mid 30s and he’s in his mid 50s and we’re both single. Would it be so bad?
Jessie in Woodmere
Dear Hot at the Water Cooler—
You’re not the first spinster who has wanted to dip your pen in the company ink. In fact, the boss/employee romantic scenario is so common that they even make porno movies about it, or so we’ve heard – we’ve never seen such a film, but we do know that they exist (check out “Nasty Dollars” as an example – a “friend” told us about it).
Having a crush on someone in a position of power is normal, but we want to give you one cautionary word of warning: LEWINSKY. You may remember, not long ago, when a girl got involved with her sexy boss and the repercussions nearly took down a little country we love called the US of A. Those dreams about her boss turned into a living nightmare for her. But that’s not the worst of it – we don’t care about a dalliance or two with a man in power – life’s short, you might as well have fun. But what’s really remarkable is that this girl is now a spinster and can’t get a man with a Cuban cigar to come within twenty feet of her big blue eyes and floppy black beret. Nothing’s worse than a spinster with a reputation of being a blabbermouth (we wanted to write something here about being able to suck the chrome off a bumper, but we’ll refrain). So, we’re sorry, but we’re going to have to stop you before you go and ruin a perfectly good blue dress – and perhaps your career.
In this case, even though you’re a spinster and we advocate that all spinsters make the most of the dating opportunities around them, you have too much to lose by schtooping the boss. We wonder – do you like your job? Perhaps your office chair is just a place where your butt numbs for eight hours a day while you read online dating profiles between surfing the internet for cute photos of cats. If you’re just “passing through” this office, perhaps a little flirting with your boss can’t hurt. And hey, if you’re dramatic enough, why not just fling the faxes to the floor, grab Boss Man by his power tie, push him up against the overhead projector and make sweet company-time love to him. It could happen.
But if you’re in this office for the long haul, then we suggest you stop doodling “Jessie loves Mr. McCreedy” on your steno pad in your cubicle, and instead take a trip to the mailroom to see what packages you can find down there. Sometimes a spinster just needs a little ego boost – and the mailroom probably has a lock on the door. Normally we wouldn’t advocate that a spinster kick over the mail truck to find a guy, but you mention that you may “slip and say something stupid” in a meeting, and we want to help you avoid that by distracting you a little. Busting out with “The expense reports this quarter are I want to stroke you hard and smother you with my panties in the supply closet” during an important meeting with the overseas clients may get you a reprimand from HR – or fired. But just so you know, a dalliance with a younger mail cart boy is like “spinster crack” – it’s a quick fix, but eventually, when you come down from the high (and hopefully haven’t sold your grandmother’s TV), we want you to find someone age appropriate and worthy of you.
The good news is that the “boss crush” will wear off and you can find someone else to actually date. You probably don’t have much of a future with your boss, but who are we to say that for certain. By the way, where do you work? We may have to come in and meet your boss in person to be sure that our advice is correct. He’s single, you said, right?
Heading out to the UPS store,
The Spinsters
Got a Question? We’re here to help.
Email us. Now. You have no time to waste.
Yes, we’re still single. So how can we help you, hottie spinster who wants to find true love? Well, we have over 40+ years of collective dating experience, the good, the bad, and the fugly (can you believe we just admitted to that?). We’re not going to tell you what to do -- that’s your mother’s job. We’re going to tell you what NOT to do. How to avoid wasting any more of your precious time on guys that don’t deserve a second look. We’re going to give you both the spin and the straight deal on what you’re doing “wrong,” or in reality, what THEY are doing wrong -- after all, our motto is “it’s not us, it’s them.” We stand by that and we’re willing to give you your money back if our advice doesn’t work for you. Of course, our advice is free, so don’t spend it all at once.
Email us here. We're at your service.



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