Young People Are Stupid, And That’s Okay: The KSK Sex & Fantasy Football Mailbag

05.24.12 6 years ago 101 Comments

I’m at the stage of wedding planning where my fiancee and I are going through all of our photos for the slideshow that shows us as babies, then as little kids, then as young adults, then together and in love. If you’ve been to a rehearsal dinner for a wedding between two white people, you’ve seen a slideshow like this before, and it was probably set to Rusted Root. (Note: mine will NOT be set to Rusted Root.)

I bring this up because I had to sift through a lot of photos of myself in my early 20s, which sucks, because I had to confront what an annoying jackass I was ten years ago. Of course, I’m still an annoying jackass, but at least my pants fit and I can trust my ability to walk home unaided after going to a bar. How did Congress trust me with American lives? They really dropped the ball with that one.

Anyway, this confession is a reminder that the advice in this mailbag — and every mailbag — stems partly from guilt about being a selfish moron. I can only ask you not to do stupid things because I’ve done them myself, and it sucks — for everyone. Let’s get to your questions.

Oracles of the O-face,
My questions come from an angle you don’t seem to get as much in the ol’ bag – over-30 year old situations. First, the relationship one. I just spent the last year and a half dating a girl that my friends didn’t like. She had a lot of upside – smart, sexy, confident – but my group of friends never liked her, pretty much never gave her a chance. Partly because of that, and partly because we do very different things (she’s an aspiring actress and I’m a lawyer), I never gave it a real chance, so we did the date, break up, get back, break up, hook up, time off dance.

Sounds like a gigantic waste of time for someone in his 30s.

Now, because of some recent events with the friend group (people leaving town, year-long issues coming to a head between some of the females in the group), I’m spending less time with them and their insular judginess and negativity.

“Turns out my friends who didn’t like my girlfriend were assholes!”

Overall, I’m happy to be moving on, even if it means more quiet time. Where I’m stuck now is what to do – should I make a move for the ex (even if she’s dating someone),

“I’m happy to be moving on. Should I try to get back together with her?” That was you, just now.

peace her out for good (and call it a lesson learned), or go off and date some other ladies (without making a firm move either way)? I gotta get unstuck, and when faced with these unknowable options, I always choose wrong.

Stop worrying about women and focus on yourself. Throw yourself into work, pick up a new hobby, go to the gym twice a day, volunteer your time at an animal shelter, whatever. All of that stuff will make you a healthier and happier person than trying to find a new (or old) flame to spend time with. The benefit of these new activities — besides making you feel healthier and happier — is that you will LOOK healthier and happier, which will make you more attractive to women, who will want to know about this mysterious, happy person who isn’t desperately trying to have sex with them.

Now fantasy. My league has been going for a while (since Sophomore year), but in the last 5 years it has been on life support. Even though we are almost all in the same town, we can’t even get anyone together for a draft. I have to manage the finances, arrange everything, do all the smack talk and send out the updates. I’m just kinda sick of the lameness of the league. BUT, recently, a friend in the league got in a bad car accident, and even though he’s going to make it… still. The question, do I run the whole league this year just to try to keep people together, or is the time and money better spent going on a guys trip?
Aged and Confused

So your group of friends can’t get together for a draft in the city they live in, but they ARE willing to go on a guys trip? AND they don’t approve of the people you date? Sounds like you have the best friends ever.

I don’t know what to tell you. You’re in your 30s. You don’t want the hassle of being commissioner? Hand off the reins to some other sucker or shut down the league. Go on a guys trip or don’t. I really don’t think this is the sort of thing you need my input on. Unless your trip is to New Orleans, which is awesome. You should definitely go, assuming your friends aren’t unreliable twats.


Dear Captain Caveman,

I just got out of a 16 month relationship a few weeks ago with my first girlfriend. It started when I was 19 and she was my first everything, kiss, relationship, etc… yeah I am a late bloomer.

Eh, it’s not THAT late. There are plenty of people who don’t get going until after high school.

The split was rather amicable. She started feeling things about another dude in her school and was really beating her self up about it, plus she intends to study abroad in a whole year in 2013-2014 (while I would be at graduate school). We decided that we didn’t we didn’t want to live with this over our heads for a year and decided to split up now and remain friends, which is cool, since we have a ton of interests in common, and we left the door open for a future relationship, too. (Only major hangup, she loves to travel, and I got a phobia of flying).

How long should wait before pursuing relationships and hookups?

You’re 20 years old. Stop reading this mailbag and go get some ass right now. I’d also rethink going to grad school unless your parents are crazy rich. Oh, and a doctor can prescribe you some sedatives or anxiolytics for your fear of flying.

I am not heartbroken and haven’t cried once. I am still friendly with my ex we still text when something relevant pops up about our mutual interests, no flowery how is your day b.s. I enjoyed the times we spent together, all positive memories. But I am looking forward to starting something new. Is this normal?

Yes. You’re 20. Let your dick guide you. Don’t try to fight it.

Also do you think I should aim for hookups or relationships? I really don’t have a group of close friends who like to go out, and not once in my three years in college have I actually gone out with buddies to drink, and club, and all that jazz….yeah I fail at being an upperclassman residential student….

“I’ve had one girlfriend in my life, and I’ve never really gone out in three years of college. Should I aim for hookups or relationships?”

You should be happy any time a girl wants to have physical contact with you. Hook up with a girl, and if you like each other, keep hooking up. If you keep liking each other and decide to only hook up with each other, congratulations: you are in a relationship. Don’t try to run when you’re still learning to walk.

Do you think I should get out of my comfort zone and actually go out (it takes me a while to adjust to new environments), or throw my own get together, since I am turning 21 early in the school year?

Yes to both. Socialize. That’s how you meet girls, which is the first step to either hooking up with or relationshipping them.

Do you think I should mack it to my female friends see who bites?

I think you should not say “mack” like that.

Or troll the internet for ass, or my idealized relationship (aka look for a girl who likes politics and/or sports)?

The word you’re looking for is trawl. And no, you should absolutely not be looking for girls online WHEN YOU LIVE ON A COLLEGE CAMPUS.

Jesus Christ.

For dealing with my white girl problems, here is a picture of Stacy Keibler, with A-Rod’s less attractive, more manly girlfriend in the background.


344 x 425 pixels? You’re too generous.


Fancy Gentlemen,
Football first: I consider myself an average fantasy player and my biggest weakness is probably drafting QBs. Last year I lucked out by drafting Aaron Rogers 9th overall then went on a rampage right up to the championship (which I lost by 6 points). That was a savvy move. I can’t say it was intentionally savvy though as I almost drafted Copspeed with that pick. Outside of drafting a top tier QB in the first round what’s your advice for drafting a QB that can help my team get to the championship? Who do you consider guys that are good value picks in the 2nd or 3rd round?

You’re not really going to get any sneaky value for a QB in the 2nd or 3rd round. Rodgers and Brees and Brady are the most reliable week-in and week-out. Cam Newton belongs in the discussion after that monster rookie season, but some people are worried about a sophomore slump. Peyton Manning is a high-risk pick with potentially big rewards. Outside of those guys, I don’t like the value of any other top QBs in the 2nd/3rd round — Romo, Eli, and Roethlisberger can all put up numbers, but they’re just not as consistent as the other guys. If I miss out on the early run of top-tier guys, I’d rather try to snag Matt Schaub a little later and hope that he and Andre Johnson can stay healthy.

Sex: Not really a sex question. I have an incredible girlfriend who loves sex, is hot/probably a little out of my league, etc.. My question is what is your opinion on emoticons? She uses a lot of them and it’s rubbed off on me. I have a friend who says if a guy puts a :) in a text that it’s “gay.”

The only thing that’s “gay” is having a sexual attraction to the same sex. Still, it’s best to think of a smiley-face emoticon as a kiss on a cheek: fine for woman-to-woman and man-to-woman interaction, much less so for man-to-man.

I have to admit I kind of used to have the same opinion. Now I like them and my texts come off as robotic and impersonal when I don’t use them occasionally. It doesn’t bother me much what other guys think but I’d be interested in your opinion anyway.

I am a grammar snob: we all know this. I detest you’re/your fuck-ups, I insist that “all right” is two words, and I get upset when people think the word insipid means “stupid.” When I first started surfing the World Wide Web (that was the term we used 40 years ago when it was invented), I was pissed off by emoticons. They were an inexcusable shortcut, a replacement for words that would lend the message greater meaning.

But I’m a writer first and foremost — and writers have to accept two truths: (1) language is always changing, and (2) the primary objective for any written work is clear communication. And as texting and instant messaging became a bigger part of my life, I found that my sarcasm often didn’t translate in my messages, especially if I was talking to someone who didn’t know me well. So I’d occasionally use them in text messages. Then I started using them ironically in headlines – KARDASHIANS GO BANKRUPT, GET CANCER :'( — and eventually I just kind of accepted that sometimes, in certain media, emoticons were the fastest and easiest way to communicate responses.

In short, I fought it until I accepted that it made my life easier. Just don’t send me any winky faces, fag!


Im taking a drug that makes everything that comes out of my penis bright yellow, it is for a medical condition that isnt contagious and effects them in no way, do I need to inform any girls before I shoot my cryptonite at them?

It took me like 2 days to realize it was the drug doing it, it was kinda weird.
6 colors away from cumming rainbows

How about not shooting your jizz at them? Wear a condom, ass.


No sex question for this week, we have NFL ethics to tackle.

…zzzuh? That’s a new one.

Without going too much into my moral/ethical background (and I’ve left out a number of opinions/counterpoints/etc in subsequent points below for the sake of brevity), I am squeamish at the thought of continuing to support the NFL in a financial sense. I’m a huge football fan at all levels, but shudder at what the league has become and its current direction. Between the ridiculous lockout, Goodell’s missteps with the handling of the Saints, the oncoming train that is concussion lawsuits, the franchise operators er “owners” who continue to bilk taxpayers for every last nickel (see Drew’s Vikings), I have issues with continuing to feed the beast, aka consume the NFL product in its various forms. This includes fantasy football.

That’s admirable. Not anything I’d ever do, but still: good for you.

My question to you (and yes, I realize your schtick is to opine and provide entertainment on said NFL cartel) is what can I do as a fan to leave the least possible “monetary footprint” so that I can enjoy a sport I love while not stuffing the coffers of the Shield’s Partners? A friend said that I should cancel cable (so that ESPN has less to bid on football rights and the NFL Network loses revenue), and try to watch as many games at locally owned bars/restaurants, and obviously do not attend games or purchase merchandise related to the NFL. While I mostly agree, a point of contention however, was fantasy football’s impact. I view it no different than a board game or gambling with friends, whereas he thinks that somehow ESPN is monetizing my participation.

Fantasy sports are the single biggest cash cow for sports websites like ESPN, Yahoo, and CBS Sports. Clicks = ad dollars, and we all know that fantasy football users click around forever trying to figure out if Maurice Morris is a better Week 13 waiver wire pick-up than Brandon Stokley. (Side note: ugh.)

I participate for the camaraderie; a chance to win money, trash talking in emails, etc. Ultimately, it’s an innocuous decision but I’m leaning towards playing. With your knowledge of the biz, is my friend crazy to think that fantasy football’s impact is part of what’s funding $1B taxpayer-backed stadiums? Or is it such a small impact, that canceling cable is extreme enough?

You’re an ant to the NFL. Any and all actions you take to stick it to the Shield will negatively impact your life more than Goodell’s or any of his minions. Canceling cable is plenty.

Caveat for the commenters: Realizing that this is America, and there are tons of corrupt/morally bankrupt/deceitful industries throughout our nation, I find myself somewhat of a hypocrite for taking this stance because one could point to any industry that’s filled with similar (what I view to be) unethical practices in which we all continue to consume. And yes, I realize that I am but one person and it will not make a cent of difference to the estate planners of the Jerry Joneses, Dan Snyders, and Jim Irsays of the world. I will however, feel somewhat better about knowing I’m not contributing to an industry rigged to make TV execs and billionaires with a hobby even richer.


Hello Captain:
Fantasy: This will be my first year playing fantasy football. 12 person league, standard rosters and scoring. What are your top 3 tips for a successful fantasy season?

(1) Familiarize yourself with fantasy rankings before the season, then jigger the conventional wisdom to your beliefs — i.e., move up players you think will have greater value (talented players in good offenses), and move down the guys you think will have less (old running backs, Lee Evans, Tim Tebow).

(2) During your draft, find a balance between your roster needs and the talent available. You want a well-rounded roster, but you also shouldn’t pass over Peyton Manning in the 6th round just because you already have Drew Brees.

(3) With trades and waiver pick-ups, try to predict results rather than chase them. And don’t make any big moves until you’re four games into the season — you need that much of a sample size to make any kind of informed decision.

Sex: Lady reader here. I’m in my late 20s and have been with my boyfriend for 5 years. We would be talking about marriage by now if not for one thing: I absolutely do not want kids, and he is undecided. I love this guy and want to be together, but also don’t want to hold him back from something he wants (if that’s what he decides). Realistically, how long should I wait around until he decides one way or another? I don’t want to give him an ultimatum, but (if he eventually decides yes) wouldn’t it be less painful all around to be 28 and single coming off a 5-year relationship, than 38 and single coming off a 15-year relationship?
Many thanks,
No Bun In This Oven

Whoa, did you just reverse the polarity of the earth? This flies in the face of every question ever — well, except the part about the guy being indecisive.

I honestly don’t know what to do with this question. Sure, it would be easier to be 28 and coming out of a five-year relationship than 38 coming out of a 15-year-relationship, but I suppose that’s the price you pay for loving someone who can’t make a big life decision unless he’s cornered into it. Sorry, I don’t mean to give you a non-answer, but I just don’t understand how a man in his late 20s can date someone who doesn’t want kids for five years and still not have an idea about whether he wants to procreate. Fuck that guy. He’s not gonna make a decision until you MAKE him make one. Give him a polite ultimatum — or at least nudge him toward figuring it the fuck out.


Hey Captain Caveman,
Football: my buddy and I agree that Gronk is destined to bust this year. He’s coming off a record setting year, he’s been drinking nonstop since the season ended, and he alarmingly keeps wearing Zubaz pants everywhere he goes.

I don’t have proof to back this up, but I would guess that — in addition to legally consuming alcohol — Gronk has also been rehabbing and working out really hard. There are just fewer people with camera phones at the gym or practice facilities. I also don’t think that wearing Zubaz negatively affects on-field performance, although it should.

Do you think he will flop hard?

No. But any reasonable person should expect a regression.

When Antonio Gates was in his prime he was like, a 4th rounder as the hands down best TE, but the year Gronk had last season was worth a first round pick. Where do you think is a safe place to consider him for this year?

I don’t know. Never underestimate Tom Brady’s troll powers — he may decide that he wants Aaron Hernandez to break Gronk’s records just to fuck with fantasy owners, and then where will you be? I think I’d wait until the 4th round to grab Gronk. I suppose that’s too conservative, but I’d want to evaluate this year’s performance before I start using a 2nd-rounder on a tight end — even if it’s the tight end with the season in NFL history.

Potential sex: 2 part wedding based question. I am the best man in a wedding this weekend, I am single, and historically quite poor with the ladies. I haven’t been laid in ages and figure this wedding is probably a good chance to try and hook up with a lady. Any advice on using my best man status to improve my chances? Sadly all 5 of the attractive bridesmaids are spoken for.

Your best man speech is your chance to demonstrate what a caring, witty friend and upstanding gentlemen you are — aside from getting the groom to the wedding, that should be your #1 priority. Helpful hints:

  • Drink ONLY enough to loosen up for the speech, and not a drop more. Don’t be the best man who slurs his speech.
  • The purpose of the speech is to honor the bride and groom. Be sure that that takes priority over your own friendship with the groom.
  • Above all else, be warm and sincere. If you get some laughs along the way, that’s great — but you’re not there for open mic night. Genuine emotion will win people over more than humor.
  • Close by raising your glass and addressing the bride and groom: “To John and Susie [or whatever their names are] — I hope that I can one day be lucky enough to find a love like yours.” Boom! You just said something nice and heartfelt that also advertised directly to the ovaries in the house.

Next part. It’s an open bar,


I enjoy whiskey but haven’t had many interesting cocktails with it. I enjoy it with cola which probably makes you think I’m some sort of barbarian/heathen/mouth breather. Any cocktails you’d recommend that taste good and the bartender will know how to make?
-Best Man

If something can be enjoyed, there are snobs dedicated to acting like assholes about it. Beer, whiskey, wine food, whatever — snobs gonna snob. Don’t worry too much about what anyone thinks, even if that “anyone” is a really hot girl (She’ll be attracted to you not caring what she thinks!).

Anyway, as you surely know, there are gazillions of different kinds of whiskey. Single-malt scotch, blended scotch, Irish whiskey, bourbon, rye — it can all be delicious, but the best value buys tend to be bourbon and rye because the best ones are made in America. When it comes to whiskey cocktails, I like the classics: an Old Fashioned with bourbon, the Manhattan (with rye, neat, and for God’s sake NOT in a martini glass), and if the weather’s warm and the bartender looks competent, the Whiskey Smash. (I made a video about some of these, btw.)

That said, there’s nothing wrong with ordering a Jack and Coke, which is still my go-to (along with Jack & ginger ale) when I’m in a crowded bar and don’t want to trouble a busy barkeep. Just make sure you’re the whiskey you’re mixing with cola is a well liquor and not top-shelf bourbon. THEN you’ll qualify as a heathen mouth-breather.

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