How NOT to propose a NSA sexual relationship

A dear friend of mine received this email yesterday, and I'm still confused. I'd think it was just a bit of spam or some sort of chain email if it weren't for the overwrought email she received on Valentine's Day. I can't figure out what the author thought the outcome would be from this sudden burst of anonymous missives. If you're wondering how best to avoid scaring the attraction out of your potential fuck-buddy, or if you're the one making my friend feel like she's living in the Hotel Overlook from The Shining, my step by step dissection might help you.

From: Mister Rightnow <rightnowmister@gmail.com>
Two Words Mr. President: Plausible Deniability

You should have stopped when you decided this email address was going to seem clever to Your Object of Desire(from here on out, YOD). Also, "Plausible Deniability" is not something a woman as liberal as YOD wants to see in her government's bag of tricks.

So, how are you? Well, I hope.

This will not put YOD at ease. Pleasantries work better when they come from someone identifiable.

The subject line of this email is quite intentional; it's the operating premise for what I'd like to propose.

"Operating premises" tend not to play an important role in sex, unless you are Alfred Kinsey or Masters & Johnson.

We've been friends, of sorts, for awhile now. Friends who occasionally do things together, enjoy each other's company, but don't really share lots of mutual friends or are in everyday contact with each other.

This makes you sound like a stalker, not an acquaintance.

I like you, respect you, feel warmly about you, and think you're attractive, but that's never kindled into something more than friendship. I suspect you feel likewise.

Again, this is something that would be more easily evaluated if YOD KNEW WHO YOU WERE.

Because I value that, I don't want to see it disrupted by what I'm proposing. Thus the plausible deniability.

Normal people take this risk every day. If you are that worried about plausible deniability, you are probably a sociopath.

I don't think you're in a relationship, and don't even know if you're seeking one. Neither am I, and because I may be leaving Madison in a few months, and for numerous other reasons, I'm staying single.

But I really miss being intimate with someone I enjoy being with. And intimacy, for me, can't work with someone with whom I have no emotional connection. This is particularly difficult for me because I have a very healthy libido (in the classical sense). In the past, that has led to a series of monogamous relationships, but that's precisely what I'm taking a break from now.

So heading off to some bar, or browsing personals, won't work. The first has no emotional connection, and the second presupposes a relationship (usually).

You could do away with both of these paragraphs. They both make you sound self-centered. You've known YOD for a while and you don't know if she's single or anything about what she might want from her life? What exactly is the "classical sense" of "healthy libido?"

In thinking about how I could resolve this conundrum, you came to mind. She seems to have a healthy sexual appetite, is comfortable with herself, and would be capable of viewing this as something that might be good for both of us, I thought.

My head hurts. Is being lonely and horny really a "conundrum?" Also, it's not exactly the height of flattery to tell a woman that she seems to be just desperate enough to go along with your plan.

But how do I ask her? I don't want to wreck our friendship with some drunken, blunt come-on. Or make some dramatic, in-person appeal.

WHY NOT? People do it all the time, get turned down, and move on. Overcoming the fear of rejection is a natural part of dating. Besides, if YOD was drunk as well, she'd probably at least have made out with you(NSA too!).

That's why this message is deliberately framed so that if you're not interested you don't have to even acknowledge it, and our friendship will not suffer. Above all, I'd like to keep that intact, even if it may not last beyond my moving from Madison.

You might think that this email does that, but what it ACTUALLY does is make YOD apt to look at every male acquaintance askance. How will you keep your relationship intact if she's constantly wondering if you're the wordy creep who basically admitted he wanks to memories of her at night?

Rest assured about a number of concerns: I'm not seeking a relationship. I'm not possessive. I'm not *hyper*sexual, or into any bizarre kinks (Are you?!! Hmmm!). I'm great to snuggle with (I seem to generate a ton of body heat), I love to talk and listen, I'm generally supportive – oh, and I'm a very good, considerate lover.

This reads like a paragraph from a Craigslist Casual Encounters ad. Not. Sexy.

So tell me what you think. Or not. If the latter, our friendship will continue. If the former, it could take on a surprising new dimension.

OMG WHO ARE YOU AND WHY DO YOU THINK ANY WOMAN WOULD AGREE TO BE YOUR FUCK BUDDY BEFORE SHE KNEW WHO YOU WERE?

All my best.

-(Hah! and you thought I'd sign my name here? NOT!!) ;P

Snotty sign-off. Furthermore, only a pornographic emoticon is acceptable in this context. Why not go with "Best of luck with all your future endeavors?"

Mr. Right Now will not be receiving a response from my friend, but it may receive a response from some other ladies-I'm sending it in to Jezebel's Crap Email From a Dude.