The KSK Sex and Fantasy Football Mailbag Tackles Yahoo! Answers

04.11.13 4 years ago 113 Comments

Every week for a couple months now, I’ve been all, “Hey guys, be sure to submit questions to the mailbag! The email’s right here. You can ask anything during the offseason.” And almost every week, people are like, “Whatever, the mailbag will happen regardless of whether I actually contribute anything.” And so a lot of these recent columns have been pretty thin.

Well, I’m tired of asking for you to write in and not getting anything. This week’s mailbag is two people who wrote in, plus a bunch of questions posted on Yahoo! Answers. F*ck y’all.

Let’s start things off with a lady emailer:

Dear KSK,

Fantasy: I don’t have anything. I’m sure i’ll end up with Eli Manning for the 10th year in a row. Here’s a gif of Kate Upton readusting her swimsuit top.

How does she make something so unappealing look so sexy????

By biting her lip and having big boobs. The bedroom eyes help, too.

SEX: I’m going to my hometown for the weekend and unfortunately my ex is friends with all of my friends. This used to be okay because we used to be okay but after a few drunk dials and angry voicemails on both ends we aren’t cool. The last time I texted him he texted back to say “Is this Chris?” Lovely.

So he probably deleted your number, meaning he’s moved on. (Or he was trolling you. But I’d guess it’s probably the former.)

I want to see all our mutual friends back home but I don’t want to see him. Unfortunately I know there’s a good chance he’ll be wherever they are. Do I just ditch my friends for the weekend? Do I just put up with hanging out with him even though it’ll be awkward and uncomfortable?

-Kathleen in Shipsburgh

It will only be awkward and uncomfortable if you let it make you feel awkward and uncomfortable. Hang out with your friends and enjoy yourself, and if you end up talking to him, be a civil adult. Maybe even apologize for your drunk dials and angry voicemails that led to the not-coolness. Then he can apologize too, and you guys can both relax and have fun with your friends. Just don’t get drunk and sleep with him, because that would just start everything all over again.


Dear KSK,
Sex: My girlfriend and I have been dating for about 7 months (I was out of town for a month on a hunting trip and a wedding). She’s 34 and I’m 26. Things had been relatively casual until the past month or so. I felt like it was the appropriate time to drop the L bomb and she reciprocated. We had a brief discussion about kids (both are for it). Yesterday, she asked me something along the lines of if I wanted to have kids with her. I didn’t give much of an answer since I’m still trying to figure that out myself. What should I be looking for? She also mentioned her brother and mom pressuring her to have a kid.

“I love you, 34-Year-Old Woman. Whoa, KIDS?!?!?? Like, now?”

For widest dissemination to all single men: you cannot date a woman in her mid-thirties without an acute awareness that she may want to have kids, and soon. (She also may not, and that’s fine. But it’s better to be prepared for the possibility that she does.) This is called Not Being Surprised By Life’s Most Obvious Shit.

Her financial situation is messy at best and mine is solid. I have paid off my student loans and my house. She’s about a house-worth in-debt for an English degree.

Chip Shipsley

Perhaps I’m reading too much into it, but the tone of your email suggests that you’re not prepared to have kids with your girlfriend. “I felt it was the appropriate time to drop the L bomb” just doesn’t convey the passion and enthusiasm of “I really love this woman and I think I want to spend my life with her.” Even your assessment of her finances — while certainly important — feels clinical when the issue is bringing life into the world with someone you love.

It’s entirely possible I’m reading that wrong, and you could very well want to have kids with this woman. But it seems to me that you need to put a LOT more serious thought into this.


You and your sister want different things in life. She seems very smart, career-focused, and independent, as evidenced by her saying “I don’t want to get married or have kids,” YOU IMPOSSIBLY DENSE SIMPLETON. Or maybe she’s a lesbian, who gives a shit? Stay out of her business and let her live her own life.

p.s. Indian women with Australian accents? [*boner hits desk*]


I have so many questions. Why would you marry someone who loves fishing and hates to be alone IF YOU HATE FISHING? Why can’t you drive her to the fishing spot, then take a hike in the woods? Why is divorce an option before compromise? Why aren’t you using Google? 

Buddy, NOBODY needs to go fishing several times a week except, like, fishermen. But hey, we all have hobbies, and being married doesn’t necessarily mean you have to take up all your spouse’s hobbies — it just means you have to reach a compromise when it comes to them. And if you can’t reach a compromise over something like fishing — a hobby you presumably knew she loved when you got married — you were probably never fit to be married in the first place. 



By giving him a blowjob, most likely.


Some common mistakes people make when trying to get their ex back are:

  • Trying to get their ex back.
  • Getting their ex back.


I’m no Jon Hamm, but mine tends to lean left, so it’s usually chilling on that side of my pant leg. Most pants do not have extra room in the crotch to allow for wang hang.

SIDE NOTE: This reminds me of my freshman year of high school, and the first time I fingered my first real girlfriend (which, by the way, were high-waisted in the style of the early ’90s). I had always just figured that the vagina’s location was the same as the base of the penis, and as my hand traveled downward, seemingly miles below the waist of her jeans, I thought to myself, “WHERE IS IT? HOW FAR MUST I GO?” This would have never happened if there’d been internet porn.

Anyway, being a teenager sucks.


The man will release an immense amount of energy in the form of a lightning storm around his genitals, but don’t be alarmed: it won’t hurt you. It’s just the way that you acquire all of his power and knowledge. THERE CAN BE ONLY ONE.

Also: the man will be, like, way more confident afterwards.


Whether it’s safe or not, I can’t say for sure. However, since ovens are meant for baking — not burning — things, I think you may be disappointed in the results of your attempted cremation. Your dead pet will only become a thoroughly cooked carcass, and I suspect that the smell of burnt fur will take over your home for longer than you might like.

I sincerely hope you don’t have a fireplace.

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