Ask Jack & Jill: The Age Difference, Slowing a Man Down, and More

Dear Jack:

 “I feel that many of my ex-lovers, especially when I was younger, have been slightly tainted by porn. Really awesome guys who watched porn growing up think that that’s how sex really works. How can we let guys know that you can slow down, that you can talk to her as a person not as an escort, and that most ladies don’t want to end things by having someone come all over her face? How do we break this and get back to real, meaningful, realistic sex where people want to be creative, explorative, and fun but respectful?” – Lisa

Hey, Lisa:

Well, it’s a fact that the best sex stems not only from chemistry, but also from communication. Unless you’re in that puppydog stage of falling in love, sex for a lot of men is about physical gratification, moreso than meaningful emotional connection, so we default to fast and hard and to the point (the point being to come), and my God, it feels so good we cannot believe you’re not feeling it too! … especially since so many women aren’t demanding enough in bed and just go along with what the man wants / is doing.

That said, most of us, the decent men out there, we certainly feel like a million bucks if we feel like you got off too. We want to feel like good lovers, so we’re way more open to direction than you think. Take control. Tell us to slow down, kiss you, look at you, grab us by the face if you need to, reel us in, walk us through how you want things to go — because trust me, we’re easily pleased, compared to you. Be subtly pushy, which is both a relief and dead sexy. Get us in sync with the emotional aspect of sex and we’ll walk away with our minds blown and you’ll walk away sexually satisfied too, and we’ll get to feel good about that. When I was younger, I’d occasionally find myself in bed with a woman who really took control, grabbed my roaming hands and just held them while we kissed instead; she’d crawl on top to set the pace, crawl off before I finished to mix things up, and it was plain enthralling. she really slowed things down: music, ambiance, hours worth of falling in love and not just fucking. I mean, there are songs that came on during those sessions that, when I hear them now, I can put a meaningful face to.  I fell in love with those women. I didn’t just pack up and go home. So, don’t be afraid to take control and leave a lasting impression! Left to our own devices, we men might rush through what could be a life-changing night. Beware, however: there’s guys who don’t particularly care what you want, and will resist you enacting said advice above. I’d recommend not sleeping with those men, you’ll be doing your gender a favour.

Dear Jill:

“Dating in St. John’s can be hard. It can be scrappy and slim pickings. Sometimes, it causes us to date outside of our general demographic, and I think that is a good thing. [But] I’ve noticed that it seems to be only men 10-20 years older than me who are interested in pursuing me. It’s giving me a bit of a complex. Is this just a byproduct of the scene? Is this healthy? Why is it that twenty-something men aren’t asking me out? What do you think is the maximum age difference possible in a couple?” – Daddy Issues

Dear Daddy Issues,

Be open minded and date all kinds of men!  Age means nothing really. It’s more about the connection. There’s absolutely nothing wrong (or unhealthy) with dating men in their mid-thirties or mid-forties. It really depends on what you are looking for in a partner and how important an age difference really is to you. If the thought of dating someone older is a complete turn off, then of course, don’t do it. Hold out and wait for someone your own age to come along or join a dating site and weed out anyone over the age of twenty-nine.

When I was eighteen, I dated a twenty nine year old and when I was twenty six, I dated a nineteen year old. Those experiences were wonderful and I learned a lot from both of them. And, to be honest, there wasn’t much of a difference.  I think you should focus on the kind of guy that is asking you out instead of the age of the guy doing the asking. Just have fun with it! I really don’t want to generalize here, but often, men that are a little older come with more experience in relationships and love and dating. Of course, that’s not always true. But it can be.  Depending on what you’re looking for, this can be a great thing.

I can’t quite say why men your own age aren’t asking you out. But I can say that I know some amazingly wonderful thirty and forty year olds that any woman would be more than lucky to have as a partner. Maybe one of those guys is pursuing you … go for it!

“What am I suppose to do to a woman’s clitoris, exactly? To be honest, going down there seems a very daunting task. All the jokes and shows and stuff talking about men not knowing what to do down there doesn’t help relieve my nervousness.” – Guy

Dear Guy,

It honestly depends on what woman you’re looking to go down on. I wish I could give you a step by step guide but there isn’t really a manual that could cover every woman in existence. We are all so very different. Some women like direct stimulation; some are simply far too sensitive for that. Some women like it fast, some slow. Some women want it rough and some want the lightest of touches.

The only rule I can give you is to go down with enthusiasm. Already, I know you’re going to be fan-fucking-tastic at it, simply because you cared enough to ask this question. Great first step, champ! Take your time and pay attention to your partner’s reactions. The old “write the alphabet with your tongue” thing can be a great starting point. Experiment with pressure and speed. Listen for moans of appreciation! Also, you could always ask her what she likes or better yet, ask her to show you. Good luck! I’m sure you’ll be awesome!

Jack & Jill will each answer two of your questions, twice a month. Submit, anonymously, with the form below. 

[gravityform id=”2″ name=”Ask Jack and Jill”]

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2 Comments

  • Your “jack” seems to be a bit of a jack off. Women would lose it if I told them that advice as a dude. Srsly. Jill seems ok

    • Yeah, these kinds of columns are an editor’s nightmare, trust me … coaxing “Jack” to say what he ought to say might defeat the purpose of people having access to an honest response to an honest question from an average joe kind of guy, but still, there’s wording we’d ordinarily have changed there, and then there’s the fact one man can’t speak for all men (but hey, people requested we have a Love and Sex Column). So I’ll reiterate: Jack’s opinions are not those of The Overcast! As well, “Jack” is actually two different men: the man who answered the first question and the man who answered the second: two different men. (“Jill,” for the record, is the same lady every time.)

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