The KSK Sex & Fantasy Football Mailbag Is 100% Party Zone

06.13.13 4 years ago 32 Comments



Hello friends! In case you haven’t noticed, summer is in full swing (don’t bring that solstice crap around here). As a married man, my summer involves family vacations and going to the park to sit on blankets with friends while we watch dogs and babies play. This is fine: it makes me happy to spend time with people I love.

But YOU, single people… YOU have a responsibility to SEIZE the summer. Make the most of the sunshine. Spend too much of your money for a share of a beach house where you don’t even have a private room. Hook up with strangers. Drink on rooftops late into the night. Get naked in the ocean at 3 a.m. Have the sexiest goddam summer ever, because you only get so many. [*scary ghost voice*]

On to your letters.

El Capitan,
Sex: Hey, the last letter in this mailbag is me from about 20 months ago. Very soon after, I met an awesome 20-something lady who I’ve now been dating for almost 2 years and living together for one. She’s half my age plus seven (up top, bro!). The sex is great and varied, impotence is very rarely a problem for me anymore, and we make each other really happy. So, thank you very much for your advice; I think I’m living the best-case scenario from the jumping-off point of that letter. Now, on to the question: She’s also into ladies, and we’ve discussed having a threesome, but as fairly shy people (me moreso than her), it’s difficult to figure out how we’d find ourselves in that situation. We’ve looked at Craigslist a little, but since we’re in a smallish city, we’re concerned that we might run into someone we already know. Any advice on how to find that rare and precious unicorn, either where we live or when traveling?

Don’t go looking on Craigslist just hoping there’s a girl looking to pair with a couple — post your own ad. If one of your friends or acquaintances responds to the ad, then you don’t respond.

Fantasy: I’m not a player here, so I humbly offer this Mamie Van Doren photo instead (she reminds me of my lady).


Best regards,
Back In the Saddle!

Your wife is 82 years old? Gross!


Dearest Kolber Konnoisseurs,
Sex first: I’ve always been notoriously quick on the draw in the sack, but over the holiday weekend with my long distance girlfriend, I found myself in an unfamiliar situation the last morning: completely unable to get off right away.

“Hooray!” — your girlfriend

After a little while I freaked, thinking it just wasn’t going to happen, and started fantasizing about other women, which ultimately (finally) took care of it.

So while HOLY SHIT that was great, should I be worried at all about the fantasizing? I love this girl and think she’s incredibly sexy – had some of the best sex of my life with with her – so I guess I was desensitized from a long weekend of sexy time? Regardless, I’m trying to shrug it off.

I don’t think it’s anything to worry about unless it’s a habit. Like, if you can ONLY get off by picturing someone else, then you have something to worry about. As it is, your p33n was probably just tuckered from a weekend of overuse. (Another reason to avoid long-distance relationships: sex organs shouldn’t be treated like camels.)

Lastly, it’s a no brainer that I shouldn’t discuss this with anyone involved… right?

Fantasy: Kind of a boring question, but I say that a safety should count more than a turnover since in the context of the game it’s essentially a turnover plus two points, but everyone I talk to thinks I’m crazy and that it should only be 2 fantasy points. What say you?
Morning Wood Works!

I agree, but I see both sides of it. It’s a rare and difficult thing for a defense to do, so I say let that defense have three fantasy points. On the other hand, safeties often comes with the additional points from a sack or forced fumble (if it goes out of the end zone), so you only get a two-point fantasy safety for holding penalties in the end zone or running backs stuffed at the line.

I guess what I’m trying to say is that I don’t really care either way.


Dear KSK,
Sex: I’m the best man in a wedding in a few weeks and have no idea what to toast. The groom and old friends that aren’t real close anymore and he cheats on his fiancée all the time and doesn’t intend to change. She’s oblivious. Any ideas? All I know for sure is that it’s gonna be quick.

FF: None. Sorry. The offseason sucks.

Yeeeeeee-ikes. I mean, the moral high ground here is “convince the groom to call off the wedding, and refuse to be the best man if he doesn’t.” But you know what? Sometimes the moral high ground isn’t realistic. It’s just a cloud: visible and seemingly attainable, but no place to stand unless you want to fall to your death.

The three hallmarks of a good wedding speech are sincerity, brevity, and humor. If you can only do two of those things, be sincere and brief. In the case of your wedding, I’d try my best to say the kind and honest things and get to the toast as soon as possible. But if you’ve got some big ol’ balls, you can always dance around the truth in joke form. “Michelle, let’s be honest: you’re too good for Jim. So thank you for doing this. Jim, I hope you realize how lucky you are. Okay, everybody, let’s start drinking now.”


Almighty Caveman,
I wrote in to one of ye olde mailbags back in ’09 concerning the soon to be long-distance girlfriend during grad school. Thank you for your help, Skype is great. This email also concerns her. We lasted for two plus years long distance before we broke up.

The lesson: if you break up INSTEAD of long-distance, you don’t waste two years of your life in a relationship where you rarely get laid.

We went radio silent for a year and reestablished contact about six months ago which has been amicable, and I saw her briefly this past Sunday for the first time since the breakup (we had overlapping layovers). That meet-up further reinforced that I am not over her. I am happy with my job and where I live, but despite intermittent relationships of varying lengths, I have not found someone who tickles my fancy anywhere close to her. As one further fact, it would likely be much more possible for me to find a job in her city, which was a key impetus to the original breakup. Advise me please! Do I write or call and confess my lingering feelings and my preference for a rekindling? And if so, anticipating a positive result (which I consider semi-likely given our mutual friend’s encouragement of the action), can you suggest next steps for us in picking up the pieces and making my eventual move to her city less awkward? If I should not reach out, how do I get over this girl?

If you are a single person, make decisions about your life and career based on what’s best for your life on career. If you are married or about to be married, THEN you should consider moving to be close to a person. Personally, I think you need to revisit last week’s post-breakup guide and give strong consideration to working on self-improvement.

This isn’t to say you SHOULDN’T find a job and move to her city. But if you do it, it should be because (a) the job there is better than the one you currently have, and (b) you think you can find happiness there WITHOUT getting back together with your ex. Be happy by yourself and your life without your ex. It’s a sure thing, whereas chasing a relationship that’s already failed once tends to be a foolhardy gamble.

As penance for the multiple questions, poor grammar, and length, please accept this photo of Blake Lively’s legs on their way to the beach, which was published around the time of my original submission.


I love my wife. I would probably push her into traffic to get a better view of Blake Lively. (Sorry, honey.)

Fantasy question: I suck at fantasy football so this might be a stupid question. I am currently in a keeper league with one keeper allowed. I have Andrew Luck I took in the 9th last year, and Purple Jesus I somehow got in the third last year (all packer fans in the league). Who do you keep? And yes, it is indicative of how bad I am at fantasy that I still missed the playoffs despite getting PJ in the 3rd.
Thank you in advance for your help!
Vaginaless in Vikingland



Sex first because there’s still two and a half months till fantasy football season starts. I just had a second date with a girl that went really well, but late in the date she mentioned that while she’d like to continue seeing me, she’s not sure about a serious relationship working because she lives about 25 minutes away (45 minutes to an hour or more in traffic) and I work fairly long hours as a lawyer. It made me a little nervous that she felt the need to flag the issue on a second date, but our first date conversation hit on the fact that I am at the point in my life where I’m only looking for a relationship if I feel like there’s potential for it to go somewhere long-term. She joked that she would take the second date as a proposal if it happened and I explained that it just means I may take a little longer to commit to a relationship because I want to get a good sense of a person first. Nonetheless, we wound up hooking up, having a great time and are supposed to grab dinner again this week.

She’s just protecting herself by lowering her stated expectations. You know how some women are cool with being friends with benefits, until three months later they’re like, “We need to talk about where this is going”? What you’ve got is sort of the philosophical reverse: she’s stating up-front that she doesn’t expect much, but I think you’ll find that she’s open to something more serious if you two continue to see each other and things progress well.

Today, a girl I dated for a couple months in the fall messaged me and at the end of catching up, asked me out for drinks. We stopped seeing each other because she felt like there was something missing that made her unable to commit to a relationship (our first relationship talk happened too early as a result of way too many shots of jameson on a pub crawl). After we stopped seeing each other, I took a 4 month break from dating to figure out what I was looking for while devoting my winter to snowboarding and then taking up crossfit at the end of ski season.

Life must be pretty rough for you.

I started dating again a little over 2 months ago and have been out with a few girls, but the latest girl feels like something different. She has an awesome sense of humor, is driven and super attractive, and likes my awkwardness that she seems to bring out in me. Despite that, her comment made me worried that she’s already made a decision about where things are going and I don’t feel the need to pursue things if she doesn’t think there’s any potential. Am I making too much out of her comment?

Yes. See above.

To go into this just a little more, you’re a lawyer and fit and outdoorsy, and you have excellent taste in reading material. My amateur analysis: she sees you as a pretty good catch, thus someone she could fall for, thus someone who could hurt her. She’s just wearing a little emotional armor.

If not, do I go out for drinks with the girl from the fall who also has the traits I’m looking for in a long-term partner and see if me being in a better place makes things different?

I mean, it’s still early with the girl you’ve gone out on two dates with, so you COULD go out for drinks with the girl you dated before. But why muddy your feelings up by playing the field? If you like someone, give it a chance and see it through.

Fantasy Football: I won my league for the first time last season behind 3 strong running backs (Gore, Charles, Spiller) and 3 strong wideouts (Megatron, Roddy White, Wayne), but my QB situation was a nightmare every week because I was stuck deciding between Phillip Rivers and Josh Freeman


since I spent my first 4 picks going WR, RB, WR, RB. Do you think it’s feasible to wait till the 5th round to draft a QB again, or should I be going back to my normal stategy of taking a top tier qb in the first couple rounds or early third and write last season off to a number of lucky picks working out?
-Troubled by Good Problems

I kind of touched on this recently, but there seem to be a lot more choices for acceptable fantasy quarterbacks than there were two or three years ago. Personally, I like getting my QB in the first two rounds (MAYBE early third), but the fact of the matter is that there will always be SOME hole on your roster that frustrates you. Better that it be at a redundant position like RB or WR than at quarterback, where you’ve only got one guy to carry the position’s points load.

Ha, “load.” Good way to end the mailbag.

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