Nanny Dearest, Premature Planning and Tangled Tricks

Nanny Dearest, Premature Planning and Tangled Tricks

Why you should care

Because you can’t spell S-E-X-Y without S, E or X. And even Y. Which is what we’re here to help you with.


All in the Nanny

EUGENE, SIR: My ex, with whom I am friendly, is pregnant and engaged to be married. This is not a problem. I recently expressed a “mild” opinion that her situation was somewhat “unusual,” and she flipped out and is demanding an apology before continuing our friendship. I like our friendship but feel incapable of complying … she is going to marry the son of another guy she used to date. I think marrying someone whose diapers you used to change is somewhat unusual, and apologizing for it seems ridiculous, as I can’t be the first one to say this. Should I just swallow and say sorry for the sake of keeping the peace? —The Professor

Dear You Sure Can Pick Them:

I was once at a new nightclub in Krefeld, Germany. There were about 10 guys there when I arrived with four other guys. It was, it should be noted, not a gay bar. Women passing by would hear the music and stick their heads in the door past the leather curtains. All of the guys would look up expectantly, and the women would freeze, back out slowly, possibly muttering something about “sorry.”

I tell you this story because you’re failing to pick up on what these women knew right away: When confronted with Crazy Town, best to avoid Crazy Town. I am unsure of when exactly you should have known this, but I am suspecting that right around the time of “I’m dating Jimmy’s son … the same son whose diapers I used to change,” you should have understood that continuing to exist in this place in space would require you to swallow hard and express no opinions counter to the prevailing orthodoxy of “don’t ask, don’t tell … specifically the police.”

There may be plenty who would opine “you go, gurl” in the fact of May-Septemberist cross-generational love, but I’m a firm believer in Occam’s razor, and Thanksgiving dinners with your ex, her ex and his grandchild are about as far from the simplest solution as you’re likely to find. Presuming, however, that “Dad” was over 18 when love hit, we can acknowledge that “love is blind” and “it takes all types.”

But should you apologize? I wouldn’t. Your intent and even your words were not mean, cross or ill-intended. After she hears the exact same thing and worse from the next 20 people, she may realize how much equanimity you brought to bear in characterizing just the barest tip of her completely whacked-out iceberg of relationship confusions.

The Early Bird

EUGENE, SIR: I am a single guy, 25 years old. I am often single, and even more so since my past few sexual encounters have ended too soon. Way too soon. Way, way too soon, if you know what I mean. So now I think it’s easier to avoid than to deal with this premature thing, but I am really not so interested in having this be my life. Advice, please. —Name withheld

Dear It’s So … Over?:

A friend of mine was once scheduled to interview some porn star. In the back-and-forth emails, things had started to heat up between them, and as the day, and then night, of the interview approached he was lit up with anticipation. I waited by the phone like De Niro in Goodfellas. And like De Niro in Goodfellas, by phone conversation’s end I was also smashing my phone. Because in preparing for his date, my friend had pre-masturbated in order to avoid the self-same problem you’re describing. He just did so too close to the time of his meeting, and so by the time the two of them were together he had slid over the divide from “caring too much” to “not giving a crap,” and after about 20 minutes of questions, he bid her goodbye and went home and watched The Sopranos. Not the way any decent sex story is supposed to end.

But within the story is a kernel of process-based truth, and that’s that if you’re going to, um, WIN at screwing, you have to attach yourself to screwing like any other kind of athlete. Which means, while it’s supposed to be spontaneous and all, you can plan for it in the very same way you might plan for rain. Because it’s better to be prepared and not need to be than to not be prepared and need to be. No “reputable” “sexologist” would probably advise this, but I will, because I am not that: pre-masturbate. If you have an evening date, the night before or the morning of might help delay your TTO, or time-to-orgasm.

Also, and here’s the presidential-level stuff: Your TTO is much less significant in this instance than your partner’s ACTUAL orgasm. Which is to say “premature ejaculation” is only called such in reference to your partner’s orgasm, so get your partner off first. And you’ll find your orgasm can come any ol’ time. Or not. No one cares! Got it? Gooooood …

Prostitution Protocol

EUGENE, SIR: When I was single a few years ago, I went to a prostitute for the first time. I paid for an hour. She wanted to massage me to “start things off.” I told her I wasn’t interested in a massage. She then screamed, “Oh! I guess you just want to SCREW, then?” Then she threw herself on the bed and just laid there. I got angry at what felt like her attempt to pad out the hour. So I had sex with her for, I believe, 59 minutes and 30 seconds. I was laughing about it with some friends, and my girlfriend (who was there and had heard the story before, but had missed the details) got angry with me. She said, “It’s not the sex. I’d be angry if you had treated your waitress like this.” I am confused about what “like this” means. Are women who have sex for money no longer expected to have sex for the money? —Missing Something

Dear MS:

My plumber tells me he is not a plumber. It’s just a “side gig.” He tells me this while knee-deep in a backyard trench. My gardener is not really a gardener; he’s designing an app and just gardens to make some “extra money.” It’s epidemic, this desire for the social climb. And I believe prostitutes are no different. I suspect the anger at you was because you were making light of what’s a hard job, but if you’re any good in bed, which your girlfriend might have a good sense of, I’d really question if 59:30 of sex would or should be considered a “hard job.” Unless she hated you, which I suspect she did, or she hated the job, which I also suspect she did. Here’s hoping she did what people who hate their jobs should always do: quit. Now go make up with your girlfriend.

OZYWildcard

Square pegs. Round holes.