KSK Sex & Fantasy Football Mailbag: The August Survival Guide

08.02.12 5 years ago 53 Comments

It’s August. August gets a lousy rap, and justifiably so — most of the country is under a blanket of withering heat and humidity, nothing happens at work because all the rich people at every company are on vacation, and — this year’s Olympics aside — baseball is the only sport going on. It sucks.

But there are rewards in August for those who make the most of it. You single folks out there should be going out to parties and the beach and enjoying the time-honored tradition of the summer fling. These are the final weeks of women barely wearing any clothes and should be duly cherished. As for those slow, boring work days? They’re perfect for laying the groundwork for your fantasy football season. Start tinkering with your player order now, and you won’t be so sweaty-palmed when you put on the finishing touches the day of your draft.

See? August isn’t so bad. Plus, you know, popsicles.

On to your questions!

Dear Caveman,
I’m going to propose to my girlfriend and I’d like to ask her father for permission to marry her (I know there are conflicting opinions on if you should or shouldn’t, but they’ll both appreciate it so I’m doing it). I’d prefer to do that in person but we’re in California and he’s in the midwest. I’ll have an opportunity to ask him at Christmas, but I’m not planning to propose until after I finish grad school in May. My question is: is it weird to ask him for permission 5 months before I propose? I realize it’s weird that I’m even thinking about it almost a year in advance, but fuck it, I’m a planner. And just out of curiosity, did you ask your father in law? How’d that go?

I don’t think it’s weird to ask five months in advance. Just be sure to give him a ballpark idea of when you plan to ask her, so he doesn’t spend the next few months wondering if you’re chickenshit.

I did indeed ask my father-in-law for his blessing, though not in the strictly traditional sense. I told him that I was going to propose to his daughter, and I’d like to do it with his blessing. That way, I satisfied both my traditional leanings and my desire to make it clear that I’d do it with or without his blessing (not that it was really in doubt — he and my mother-in-law have always liked me). Nevertheless: it’s nerve-wracking as shit to ask a man to marry his daughter. Good luck.

And as for football, I brought the same girl to my draft last year. She’s a big fan of The League and wanted to co-manage a team. Turns out she’s really good at it (she uses logic and reason to make picks whereas I want to draft players with cool beards) and we ended up with the best team I’ve ever had. No one complained about her being there and it’s not a bro-filled league, though it has been exclusively dudes throughout its history. Am I that guy? I don’t want to be that guy. I just like playing fantasy football with my girlfriend.

If nobody complained and your future wife didn’t make any faux pas, I don’t see a problem. Enjoy.


Oh wise neanderthal of carnal and fantasy knowledge,
Fantasy: The past few years, Drew Brees has always been a safe bet as a pick for me. Even the year where he had the nagging knee injury, he carried my squad through numerous wins and to the semi finals of my league’s playoffs. With all the question marks with the Saints this season, however, would it be a good idea to go after him again?

I think so. The off-field stuff may make for lots of headlines, but at the end of the day it’s still Drew Brees throwing to Colston and Graham and Sproles.

Sex: No real complaints in this department since my girl and I have been getting along swimmingly for over a year now. We support each other’s geeky interests, the sex is bombastic, and I can talk and share anything with her. I think it’s safe to say that I found my dream girl and we are head over cleats in love with each other. So much so, that she popped the question a few weeks before my planned proposal on her birthday!

That seems a little weird to me, although I would have happily accepted a proposal from my wife if it meant she bought the engagement ring.

Enough my bragging and on to the question. We’re planning around September – October for the wedding date, so I just wanted to know what lies ahead for me within the next year.
Thanks a bunch,
VooDoo Child

A period of excitement and delirious love that leads to grueling weeks and months of discussions about flowers and invitations and seating arrangements. Planning a wedding sucks New York City summer garbage juice.

P.S. Just in case this question is a bit weak, I’ve attached an oldie but goodie for you and the Commentariat. The GQ spread of the woman that is on both my and my fiance’s cheat list, Rosario Dawson. Enjoy.

That’s good hustle.


Hey Uff,
I don’t really have a sex question (booooring), as I just got engaged, so I’m enjoying all that wonderful sex that will surely be shut down the instant I say “I do.”

Marriage doesn’t shut down sex. Kids shut down sex.

This year is the first year I will be commissioner of a fantasy league. I don’t have a lot of experience with fantasy football, so I’m totally unqualified for this, but no one else I know is willing to do it, so I figured I’d go through a trial by fire. My question is multi-part: what’s the best (or your preferred) site for fantasy? Yahoo? ESPN? Something else? And what’s the best way to collect money? I was thinking of setting up a PayPal account (most of my friends live in different cities), but I’m not sure if that would be best. Any other general advice you can give would certainly be helpful.
Anthony the Fantasy Tyro

Our own Flubby has the best advice here: “If you use PayPal, tell everyone in your league to NOT reference ‘fantasy football’ or anything similar in the payment information. PayPal considers using its services for fantasy football a violation of the terms of service and WILL freeze your account.”

As for the other question, Yahoo, NFL, and ESPN all offer satisfying fantasy football experiences. I’ve also seen people use CBS Sports, which led me to say, “Who the fuck goes to CBS Sports?” Personally, Yahoo and NFL.com are my preferred sites for fantasy, largely because I try not to go the 4-letter website if I can help it.


Football: Are the Seahawks serious with this whole Tarvaris Jackson starting over Matt Flynn business? Surely they didn’t guarantee Flynn $10MM to ride the bench? I know that preseason hasn’t even started yet and a lot can change in the coming weeks… but come on… really??

There are lots of people who think Seahawks fans are stupid because we’re excited about Matt Flynn’s one awesome game last year. They’re wrong. We’re excited about Matt Flynn because HE HAS TO BE BETTER THAN TARVARIS JACKSON. Frankly, I think the “open competition” with Russell Wilson during training camp is a ruse to get Wilson as many snaps as T-Jack. If Wilson can be a capable backup as a rookie, that makes T-Jack worthwhile trade fodder when starting QB’s start getting injured.

At least, that’s what I — a rational person with eyes — believes and hopes to be true. With Pete Carroll calling the shots, I can’t pretend to know what reality is.

Sex: I met a lady friend in grad school that I’ve been seeing for a few months. Things have been going swimmingly thus far – she’s smart, funny, attractive, is starting a great job next month, etc. We get along extremely well, I really enjoy being with her, and couldn’t really ask for much more in a relationship… but the sex is pretty bad.

Most times when we do the deed she seems pretty disinterested, like she’s just waiting for me to finish. I almost always initiate the action and usually go down on her before the deed (she’s only reciprocated once and that was because I was recovering from surgery and couldn’t bone).

We finally had a positive, honest, open discussion about it last week while lying in bed and a few things came up: I stressed to her that getting her off was a priority for me and that doing so is a huge turn on. She told me that I usually get her off when I go down on her and she just never really enjoyed the actual act of sex. I said I wanted her to be a little more aggressive and that I hoped she would feel the urge to jump on me every now and then, or go down on me, or just be the one who go the ball rolling. She was a little taken aback by all of this and insisted that she was into our sexy time.

The conclusion that we came to is that she has always had difficulty getting off from P in the V and that manual stimulation works best for her. She promised to initiate a little more in the future and to help me help her get off. She also said that she had a mental hang up – she thinks she would be more into it and would get off more easily if she knew I was committed (i.e., make an official boyfriend/girlfriend declaration). I’m skeptical on this last point; after a few months of steady dating and humping, I think things should have improved by now.

Absolutely things should have improved by now. Unfortunately, whatever you know about sex is negated by your ignorance of the female mind. You, a man who’s been “steadily dating” someone for a couple months, is “skeptical” of her opinion of what would make sex better for her? From your description, I have no doubt that she sucks in bed, but you also seem like a total coward about monogamy.

This one is worth keeping around, but I’m not convinced that putting a label on it will make much of a difference in our sex lives. What do I do… cut my losses or make a commitment and dig myself in deeper in the hopes that the sex will improve?
Lame Humps

Not everybody experiences fireworks right away. If she’s as great as you say she is, make her your girlfriend and work on improving your sex lives. Best case scenario: the awesome person you like also provides you with awesome sex. Worst case: you break up with no regrets after a few more months of underwhelming sex.


Dear KSK,
I wrote to you back in May, as a single father, getting back into the dating game about a year after my divorce.


While I was nervous as hell for my first real date following that, your advice was sound and helpful. While I have been on several first dates since then, I also decided to focus my energies on making myself happy, have gotten in great shape, feel fantastic and lo and behold I met a great girl in early June, who I now find myself in a pretty darn great relationship with…so thank you for the help.

No problem, you did all the work.

Now, my issue is this…this girl has proven to be totally understanding and accepting of my divorced status, my four year old daughter, and even the fact that I am in recovery (damn painkillers). She has been supportive of all of those issues, and I have worked very hard to be open and honest with her in every facet of my life…save for one. When I was 17 I was diagnosed with bone cancer, and after five recurrences of the disease, it spreading to my lungs and three years of fucking terrible treatment and 25 surgeries (see painkiller addiction), I now find myself 10 years cancer free (YAY ME!).

God damn. Cancer’s such an asshole.

My cancer experience is something I would never trade because it made me who I am, and allowed me to find my passion in making a difference in the lives of others in the cancer community . Now besides being left with the body of an 80 yr old trapped in a 30 yr old body (knee replacement, both hips replaced, half my lung tissue, etc) this treatment left me unable to have children the normal way, and my ex-wife and I used IVF to have our daughter. Problem is, I can’t do that same process again with anyone but my ex due to how it is done (basically all my frozen guys have been used up to fertilize my ex wife’s eggs, which we still have frozen).

I want to know more about this divorce. Who leaves a spouse with cancer? Besides politicians, I mean.

I really care for this new girl, and while I am not anywhere near the idea of marriage and/or children, I don’t know how I break this latest issue to her. I know for a fact she wants children, and while my daughter adores her and vice versa, it isn’t the same as having your own child. I just don’t know how to broach the topic, let alone have a discussion about it. I made an off-handed comment about it once before, but I don’t think she took me seriously, and we have had ZERO discussion about it since. I know I just need to sack up and tell her, but this could end our relationship, and I could use some more of your common sense guidance here. (The impetus for even thinking this is the fact we have quickly ditched the condoms during our sexy time).

I think you need to find that sweet spot between developing deeper feelings for each other and getting really serious. Like, her reaction to your news needs to be, “That’s heavy news and I need to process this” and not “How could you wait so long to tell me?” Of course, I don’t know when that moment is going to be, and it’s not like this is the kind of subject that feels natural to bring up.

Maybe the best thing to do is just sit her down and open with the caveat, “Hey, maybe I’m messing things up by telling you this too soon, but I’d rather ruin things too soon than hurt you by telling you too late.” Don’t be surprised if she’s taken aback by the news, but if she really loves you and is open-minded about the nature of parenting, you two could still have kids down the road that you’ll end up loving just as much as your daughter. I’m obviously a tyro in this department, but as I understand it, parental ties are determined more by raising and caring for the child than they are by knowing that the child comes from your genetic code.

Now as for fantasy…I play in a keeper league which is great, and I have a handle on it, but I also play in a Defense Only league that one of my buddies started up. It is a Yahoo league, and basically you have a 4-3 alignment plus a team defense. I have been playing in this league for 5 years now, and have never finished in the Top 5 out of 12. My issue seems to be with drafting, where I just don’t have the depth of knowledge of all 32 teams to really find guys that are quality players. Any advice on a good way to prepare for the upcoming draft?
Shooting Blanks…

This defensive league uses stats, yes? Stats that you can look up? Because it seems to me like Google might have some of the answers you need.


Footballs first: I run a keeper auction league and I wanted your input as to how to make the keeper system fair, but also so someone doesn’t get to have Cam Newton for $1 for all eternity. My idea was to add $10 to the keeper price in year 1, $15 in year 2, $20 in year 3 etc. Thoughts?


Sex: My girlfriend of about 2 years broke up with me on Wednesday night. I took it pretty hard, as this was the second long-term relationship that ended when I was under the assumption that it would end in a marriage. I’m 27, so I feel like I have a reasonable handle on these things, but something innate has prevented me from ever buying a ring, which is a good thing I guess. Anywho, Thursday was the longest most insufferable day of work that I have ever experienced, and I considered screaming obscenities with the end goal getting fired, just so I could go home.

Man, your boss must suck. I feel like you could walk into any manager’s office at 2 p.m. on a Thursday and say, “Hey boss, my girlfriend of two years broke up with me last night, and I’ve been on the verge of crying all day. Would you mind if I slipped out of here early today so I can get my shit together?” The person who would say no to that would have to be some kind of monster.

Side note: this is why every break-up should be initiated on a Friday. Have some courtesy.

I have never connected with another person as much as I have with her. She was without a doubt my best friend. She played the let’s be friends card, and I followed your advice and told her that I can’t do that and I’m working on the separating entirely bit. I think I’m almost to that question. I obviously still love her, but many people think we aren’t right for one another to begin with. She is very much an introvert. She likes to stay at home and sew (She’s 25, just wanted to make it clear that I wasn’t dating a grandmother) and I like to be around people as much as possible. While, this actually never created a problem because she was not overly concerned with what I did with my time, most people saw that as an irreconcilable difference. So I ask you, can two people who have very different wants and needs still make things work or should I just chalk this up as a loss and move on?
Drew Brees

There isn’t really a boundary that limits two people’s ability to find happiness with one another. My wife doesn’t drink at all, while most of my friendships are at least partly fused with whiskey. It doesn’t matter to us because our relationship isn’t built on drinking or not drinking. I would say the same goes for an outgoing person with an introverted one — as long as the two people are happy together, it’s not a big deal.


That said, your friends aren’t blind. Assuming they’re not selfish pricks who just want to keep you to themselves, they must have seen something in your relationship that restricted your self-realization or was fundamentally unsound.

Whatever the case, it’s now moot. Move forward. In a couple years, you’ll get married, and you’ll look back on this relationship and be like, “Seriously? I was upset over that needlepoint lameass?”

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