Ask Jack & Jill. Featuring a New Jack. (18+)

Big Note: There is a new “Jack” for this feature.

After the first Jack and Jill post, there was some negative reaction to Jack’s manner of responding. He was hired because of his background, fyi, not because of any sample writing. After hearing both editorial and public feedback, he decided he felt “awkward, and apologetic, and no longer interested in doing this.” Don’t hold Past Jack’s discretions against New Jack.

Ask Jack

“I’m twenty-seven, and just out of a seven year relationship. So I’m dating again. But I spend the whole date wondering if the guy thinks the whole date is us just going through the motions, so we can sleep together. It ruins my date, wondering on that, worrying. Am I being crazy? A first date is just about finding out if you want a second date, right? Everyone operates like that?” – Anxious Dater

Hi Anxious Dater,

I think my advice here is to remember a first date is exactly what you said it is: a means to find out if you’d like to see this person again. As such, and not in a selfish way, a first date is all about finding out how you feel about the other person — it’s not about finding out what they want from you that night, and it’s certainly not about delivering on their desires. So I wouldn’t worry too much about his expectations or what he wants out of the date. And remember, he might even have similar anxieties, as in, he might be thinking you’re only there for a one-night stand. If you’ve been dating men you meet on online dating sites, than I can certainly understand your anxiety: those sites are littered with people who really are just looking to hook up. That’s sad, they’re abusing the purpose of a dating website. But don’t let those kinds of men (and women!) discourage you. Be out there, meeting new people, until one of them leaves you wanting that second date, and third, and fourth, and a toothbrush at his place.

I know that’s a bit of a feel-good, unhelpful answer, maybe, so I asked a few of my male friends what they’re expecting on a first date. And I asked a decent cross-section of men. The general consensus is this: “If it’s an official date, as in, pre-arranged, and one-one-one, than no, it’s not about getting sex that night.” Hope that helps you relax and enjoy the next lucky guy.

“I’m in a new-ish relationship, and I adore the guy. Adore. I’ve been spending a few nights a week at his place. He’s got a thing for morning handjobs. Seriously. Handjobs. We’re in our thirties, and he has a thing for handjobs. And I am happy to assist those morning handjobs, but, just as soon as he’s ready to “go” he takes over himself. He kind of wraps his hand around mine in those last few moments, and his body language basically tells me to screw off. It’s deflating, as it makes me feel like I’ve been doing something wrong all along, or something that’s okay but not good enough for the orgasm moments. What’s going on here? I’m not used to jerking a guy off, clearly.” – Mourning Jerk

Hi Mourning Jerk,

If you were doing somthing “wrong” he’d never have come back for handjob 2, right? This has little to do with you, and everything to do with the finicky nature of an ejaculating penis. I don’t necessarily agree with him “taking over” as he’s about to come, as I can see how that could feel offensive for sure, but I can explain why he’s doing it. Everything you’re doing up to the point he’s about to come feels terrific, but, the second he starts ejaculating, his penis becomes twenty-five times more sensitive, and it just can’t take certain things — be it too much speed, or more likely, a constant stroking (that’s out of tune with the rhythm of their ejaculation). After spending their teen years jerking off in their mother’s bathrooms, every man emerges into adulthood with their own preference for how to handle themselves in those precious few moments.  It’s nearly impossible for you to be able to commune with his body during those moments, to read what his penis is demanding from the hand that jerks it. But as a rule it’s likely  this: stroke it in between comeshots, and pause briefly, as each shot comes out. Maybe that’s his pattern, pay attention next time. Don’t be offended, but rather, understand it’s biology’s fault for making the ejaculating penis such a finicky thing. Plus there’s the one million masterbation sessions he’s had to help foster his own ability to understand his ejaculating penis’s needs. He’s just got more experience in the matter. That said, I still don’t agree with a man taking over in those last few moments, as it does seem a little rude.

I asked a few friends if they take over during those last few moments of an HJ or BJ, and if so, why? The general consensus was, “only because a lot of women stop what they’re doing just as you’re about to orgasm, and that’s the only way to ruin an orgasm. Seriously, a lot of women stop what they’re doing just as you’re about to come, and it’s almost painful. So it’s more like I’m finishing myself off, because she’s stopped to early.”

Ask Jill

“What do you think the general rules are for dating in this city? Obviously, don’t date your best friend’s ex, or probably anyone you want to be best friends with in the near future. But where do we draw the line. It’s a small city, and if we date within our social circle, we’re most likely going to date someone who has already dated, dumped, pursued or slept with people we know. How many degrees of separation are necessary? Is there an etiquette?” – New Girl

Dear New Girl,

Ah. Dating rules are so blurry. The only etiquette, in my opinion, is to be respectful of your friends and their feelings and insist that they be respectful of yours as well. If your friend says they are madly in love with someone, then oh please, stay away. If, however, you have a friend who calls dibs on every person they see, then tell them that dibs only apply to serious love interests and they only get to have one dib…dibbee? (One person they can call dibs on.) This city is too small for that nonsense.

It’s ok to date the ex of someone you know. It’s also ok to sleep with someone that has slept with someone you know. Keep the rules between close friends. You don’t owe that girl you met at a show once and added on Facebook anything. If you know that two years ago, she slept with a boy you desperately want right now, then there should be nothing stopping you. You can’t not kiss a boy because your co-worker kissed him in seventh grade. And well, you shouldn’t hate on anyone that sleeps with someone that you dated before either unless it’s someone you’re extremely close to and you’ve made a strong case as to why you wish they wouldn’t.

Also, it’s good to date outside of your social circle. You can meet so many amazing people when you step outside of your bubble or off of the deck at Holdsworth Court! Sorry I couldn’t be of more help! I really do think it’s going to vary between different sets of friends.  For instance, if you and I were friends, I would say go mad! Date, sleep with, or fall in love with any guy I’ve ever loved, lost, slept with or crushed on. I am totally cool with it. However, I would probably not be comfortable sleeping with anyone a friend of mine has slept with. Perhaps, have a chat with your friends and make your own rules.

“So, I want you to be straight up with me. I don’t have trouble with honesty, just poor statistical analyses, because I’m a math major.Which means I know for a fact that all of the national forums on “Average Male Penis Size” are flawed because of their sample population: obviously men with small penises aren’t showing up to these things to have their little ones measured, because that’s embarrassing. The result is that these studies are flawed, because they’re weighted towards only the people who felt big and confident enough to show up to be measured. As well, in all the porn we see, the man’s only requirement to get the job is to be well-hung. So there’s this impression that most guys are 6-8 inches, and I am wondering, right from you Jill, as I assume you’ve seen a healthy number of St. John’s penises, what’s the gamut. Not the average size, but, like, how many times out of 10 do you encounter a little penis like mine (no longer than my iphone)? How many times out of 10 do you encounter one as long as baby doll arm?” – Math Man

Dear Math Man,

The average penis is usually between 4.25 -7.5 inches. These statistics come from a whole slew of studies (medical, scientific, random internet research, word of mouth) and in my experience, it’s pretty accurate. But here’s the thing, it really doesn’t matter. The only people that are usually hung up on penis size are the owners of the penis. And you’re right. Porn is indeed misleading. Male porn stars are almost always chosen because they have a large penis. This is sort of sad because a lot of men look to porn as some sort of rule on how to have a penis, how to have a body, how to have sex … etc. Porn is great but oh goodness, don’t let it ever tell you that your penis is too small.

As for me and the healthy amount of St. John’s penises that I’ve encountered, well, I’m not quite sure how to answer that. I’ve seen a penis on the smaller side of the scale and once, I saw a very large penis. Any relationships that I have been in, or any non-relationship hook ups, have been in the average range, and I preferred  it that way. Be happy with what you have. Penises are awesome. Small ones or large ones. Just like small breasts or large breasts. Small butts or big butts. Our bodies are far too fucking amazing to be dwelling on the size of something that brings you so much pleasure!

Jack & Jill will each answer two of your questions, every second Tuesday. Submit, anonymously, with the form below. 

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6 Comments

  • huh. the note at the top here, combined with the mod post in the last”Jack and Jill” really don’t help this website. i feel like most people with a clue reading the “overcast” can pick up on the editors inabilities. what this city needed was a strong, interesting and innovative alt publication. not something that essentially amounts to blogspam getting printed on a monthly basis. boo-urns for getting our hopes up, and boo-urns for making everyone think you could actually be as good as the scope. you’re not, and the scope wasn’t even that good.

    • Gert:
      The only thing that’s really wrong with this paper, or The Scope, is people like you, ragging on things, sounding like a bitter jackass trying to bring down a paper that’s trying to do a thing. As far as I can tell the first issue of the overcast was very, very well received, and it was certainly loaded with diverse an interesting content, and it looked GREAT. Unless you can articulate why you think the Overcast sucks, you simply sound like an annoying ass no one wants to hear from. So please, do us all a favour and shut up. The Internet would be such a great place if it weren’t from comment thread assholes like you. No one’s forcing you to read this stuff.

    • Gert:

      “Blogspam”
      Did you even read the first print issue? obviously not. Holy content! two page spreads, gorgeous exclusive photography, interest full-length articles. Stop being a downer.

    • I don’t think any criticism containing the word ‘boo-urn’ deserves much consideration. But I’l say this: thanks to the folks at Overcast for what has to be a labour of love, because I doubt you are getting rich or phoning it in. Jean Luc Godard said that the best way to criticize a movie is to make one. Good luck with your alt paper, Gert.

    • I’m with these two.
      Here’s what Chad’s doing: Getting a new alt paper going, and trying things out.
      Here’s what you’re doing: being a dick, and helping no one.
      The Scope: Rocked
      The Overcast: Rocks
      Gert: Contributes nothing to society.

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