Time to Stop Drinking! The KSK Sex & Fantasy Football Mailbag

05.10.12 6 years ago 91 Comments

My bachelor party was this past weekend. It was a great deal of fun, and also kind of disastrous. We started at 3 p.m. in a place in Brooklyn that has happy hour deals on oysters and whiskey, then did an early-evening cruise around Manhattan on a rented yacht with open bar. We gambled with dice raucously, and then my night got pretty blurry. I guess we also played some poker? And got into a limo and sang along to Pearl Jam’s “Jeremy”? And the limo broke down on the FDR, so we went to a bar in Alphabet City? Then apparently I disappeared for half an hour, and when I rejoined the party I was no longer blacked out. Nice! Memories!

But yeah, I woke up with this bad boy on my arm and countless bruises all over my body — I remember falling down the ladder on the boat (didn’t spill my drink LIKE A BAWSE), but I don’t recall falling face-first off a two-foot partition onto the West Side Highway. Also, the officiant of my wedding tried to walk home over the Williamsburg Bridge, fell onto his face and cut his chin open, and showed up at his apartment at 5:30 in the morning shirtless, bloody, and vomiting. His wife took him to the ER for six stitches and a tetanus shot.

Oh yeah, and there was also this:

So apparently these are the things that happen at bachelor parties that make The Hangover realistic enough to be funny. If that happens to you regularly, you should probably stop drinking entirely (more on that later, btw).

Thanks for indulging drunken story time. Let’s get to your questions.

Dear Pele of Pegging:
Football: Now that we know that Trent Richardson will be the feature back at the Factory of Sadness, in what round would you draft him?

I’d wait to see how he does in training camp and the preseason before I committing to a specific round, especially considering that he’ll probably get injured just before the season begins (because he’s on the Browns and they unnecessarily traded up to get him).

Sex: I’m a middle aged guy, and I’ve had ten or twelve relationships of varying degrees of seriousness over the years. All of these relationships have one thing in common. Each and every woman I date ends up gaining at least 30 pounds within the first six months after I start dating her — this in spite of the fact that they say that they made no changes to their diet/exercise routine. Two of them gained over 100 pounds during the first year that I dated them.

Wow! That’s incredible! I want there to be a simple yet awesome explanation, like you ejaculate frosting or gravy. Oh man, if I jizzed gravy, I would do nothing but yoga until I could suck myself off.

Are there other guys that this happens to? I know that lotsa skinny women exist, so it’s obvious that most guys aren’t having this problem, but please tell me that I’m not the only one. For years I’ve been asking myself if I’m doing something wrong to cause this, but I can’t come up with anything. Short of trying to date a personal trainer, do you have any advice?
My Wang Cured Anorexia

Before I get into this question, I do want to openly wonder about your own body mass index. I find it hard to believe that ten (or twelve) women who dated you would wantonly gain 30 pounds without you setting an unwritten precedent for being overweight. (Unless you live in the Midwest.) Is it at all possible that your women are getting cues from you? I assume that someone who values his own physical fitness would gravitate towards a woman who also cared about her body. Personally, I feel like a worthless fatass if my fiancee goes running three straight days and I haven’t gone to the gym.

Of course, if you’re a totally in-shape stud, please forgive my assumptions. Besides, what’s so wrong with dating a personal trainer? “Sorry, women with toned stomachs and muscular asses don’t do it for me.” If you date a personal trainer and she gets fat, THEN we’ve got a mailbag.


Captain Caveman,
Whenever I first get the opportunity to have sex with a girl, I can’t get an erection. The problem seems to get worse the more I like the girl. This has plagued me with almost every girl I’ve with whom I’ve ever had sex. I’ve only had sex with about 10 girls, so I know it’s a small sample size, but still. There was one girl I was really indifferent about and sex was no problem with her. In all the other cases, however, I usually can’t get it up for the first two to three times we try. Once we “successfully” have sex, I never have trouble getting an erection in subsequent encounters.

Doctors have told me the problem is mental, and I totally believe them; I’m in my mid twenties and in excellent shape; more importantly, as I mentioned above, the problem is always resolved quickly. But I’m obviously not satisfied with that: how I can fix this mental problem so that it doesn’t affect me again? EVER. Failing to get an erection didn’t cost me additional opportunities with any of these girls, but I feel mortified when it happens.
Cheesehead Errant

I apologize for using a baseball metaphor in a football & sex column, but here it is: you’re squeezing the bat too hard. (And not in an innuendo way — your dick is not a bat, and you are not gripping it too hard when you masturbate.) Baseball players don’t hit home runs by gripping their bat really hard and tensing up at the plate; they’re loose, confident. Relax: the girl you take home is not some fantastic unattainable goddess that you need to satisfy or else you’ll lose her forever. She’s just a person, with all the insecurities and desires and needs that comes from being a human being in society.

Of course, the alchemy of brain-to-wang function is better understood by professionals, so I’d recommend a licensed sex therapist or psychiatrist — maybe someone who might be willing to prescribe some Viagra if mental exercises don’t help. Then you can enjoy as many sunsets in side-by-side bathtubs as your dick can handle.


Dear Caveman,
Two weeks ago a girl and I broke things off after about four months of being exclusive, but not actually dating. The reason for said “breakup” was twofold:

1. She just moved here, so she wants to experience the city a bit before making a decision.

NOTE: I don’t know where “here” is, because you are a stranger sending me an email.

2. This is also her first time being on her own (she’s 22, lived with her parents then ex-fiancee up until she moved here). She wants to live on her own and not have to answer to anyone for a bit.

Well that sounds completely reasonable and you should probably give her her space. But hey, why don’t you go on for several more paragraphs? I’ve got nothing better to do.

She said we could still be friends after the breakup, but I know that’s not a realistic possibility at least on my end.

So don’t be friends. This shouldn’t be hard.

At the same time, the feelings both ways were (are?) extremely strong passionate, with her admitting to me more than once that she thinks about us being together permanently more than she likes to admit, and everyone—family, friends, etc.—thinking we have a stronger connection than some marriages, which in fairness is not exactly a hard standard to beat, nor is it something I especially value heavily since you hear all the time “OMG you two would be perfect together!” Nonetheless, I like to think the people I am friends with are smart and not yes-men, so their word does carry a little weight.

Are the friends who say “OMG you two would be perfect together” taking into account that she wants to be on her own in the city before dating anyone seriously? No? Then their opinions are shit.

We’ve both had very frank talks where she has said I am her ideal man, but the timing is not right. I get it—we need to check off four boxes, and only three are hit. She has said, however, when she is ready, if (and it’s a big if, obviously) I am there, we would try this again (and from the way she chats, it sounds like a foregone conclusion). This girl’s greatest strength is her honesty, sometimes at the cost of tears, and also in that she’s not one to say “oh we are definitely going to work out.” If she can’t make a promise, she doesn’t, which sometimes sucks not having a guarantee (see: exclusive but not committed) but is a quality I would think is admirable. For example, she’s said she doesn’t know realistically how long she will be single. It could be months, years or forever–she’s slipped and said “a few months” before but I’m not pinning my hopes on anything.

I understand she needs her distance right now, and I am doing everything I can to give it to her. My question is, what is the degree to which I give her space? Do I completely block her out of my life and go forward? Do I act friendly around her, be there when she needs me (and she’s not the clingy type, so she’s not going to call me up in a week because she’s desperate for sex; if she needs me, it’s because a family member died) and that sort of thing? One of my friends suggested I invite her out, but then give her the cold shoulder, which to me sounds fucking stupid since its back to high school games.

You’re correct. That’s really, really stupid.

I’m definitely not about to smother her, but at the same time, I don’t want to cut her off completely since, admittedly, I still care about her and would like it to eventually work out.

I’ll date around and not cry in my room every night, but in the long run I would like it to work. Thoughts?
Understanding yet unsure

I’ve dated a lot of people that I could have happily lived the rest of my life with if the timing had been different. In some cases, it was a serious relationship that left me devastated, and in others it was something casual that I never appreciated until after I had kissed it off and been a complete douchebag. “Hey, that person was GREAT, why didn’t you make her your girlfriend?” I dunno. Wasn’t the right time for me (or her).

So here’s how life shakes out. Now that I’m getting married, I’m not looking back on these other women I dated and saying, “Hmmm, I wonder if it could have worked out with Gisele or Marisa or Kate.” I’m looking forward to the life I’m building with this amazing beautiful woman who I wouldn’t have even appreciated when I was a dumbass 23-year-old. Those other girls? They’re absolutely wonderful human beings, and still beautiful, and I wish them the happiness that I’ve found. But I don’t regret moving on from so-and-so because she couldn’t make up her mind.

So get going, man. Ignore her and date other people. If you let her believe that you’ll always be there, she’ll treat as if you’ll always be there.

Don’t wait for her to put together the puzzle of timing — find another person who’s already got the pieces put together. If it’s meant to be, you guys will reconnect down the line. If it’s not, then you’ll end up with someone else who’s better suited for you.


Football: No specific roster question here, but where do you think the invisible cutoff — the place where you seriously consider picking Aaron Rodgers or Calvin Johnson — in running backs will be this year? I’m always torn when I’m picking late in the first round. I know almost exactly what I’m going to get out of Rodgers or Brees or Brady, but those guys aren’t winning me a fantasy league; striking gold with a running back like LeSean McCoy will.

I disagree. Aaron Rodgers WILL win you a fantasy league — or at least he did for me, last year. Of course, you need other players drafted in other rounds to win, and in my case having Marshawn Lynch step up when Matt Forte got injured was the key to winning the league.

What you need to win is to get value from your draft picks. I’d happily take Rodgers or Megatron at 7, maybe even 6. Better to get a guaranteed beast than “I sure hope Chris Johnson decides to be good again!”

Sex: Again, no specific situation here, just curious about your opinion — do you believe truly platonic friendships between men and women can exist?


A few of my friends basically rule out the possibility entirely; I tend to disagree (we’re juniors in college),

Oh, you’re 21? In that case, no. Platonic friendships are not possible.

but as much as I value the female friendships I have, it still surprises me when I hear a guy say his best friend is a girl.

Then he’s either deluding himself about a crush or he’s gay.

I could never see myself in that situation. (This is NOT meant as a friend-zone bitchfest; although if you’d like to remind everyone to stop giving attention to that special friend, go ahead.)

Girls are fantastic. They’re soft and they smell nice and are generally better at something called “emotions.” But if you’re a straight man in college, your best friend should be a man. If you rank your friends, there shouldn’t even be a girl in the top five. I mean, who else are you drinking beer and playing video games with?


Dear Denizens of the Drop-back;

Football first. My league is switching to a two-person keeper format this season. I’m struggling to nail down who I should keep. I was hoping you could swing some pearls of wisdom my way. Same situation as always, you lose the pick for the round you drafted your keeps. Here’s my team and where they were drafted:

Felix Jones – 1st
Dez Bryant – 4th
Shonn Greene – 4th
Jimmy Graham – 6th
Julio Jones – 7th
Reggie Bush – 7th
Steve Smith (Panthers) – 8th
Cedric Benson – 8th
AJ Green – 10th
Cam Newton – 16th (obvious lock)

I’d keep Newton and then… AJ Green? Did I really just type that? Obviously Jimmy Graham is also a stellar pick (hell, a lot of those guys would be worthy keepers on lesser teams), but I have a tendency to lean towards the guy in the lower round. You’re more likely to get someone close to Graham’s value in the 6th than a breakout WR in the 10th.

As for the sex life – there isn’t one. I work in a job which requires confidence, good looks, high dress standard. I’m 24 in a couple of weeks and am yet to have a relationship I’d categorise as serious. At max they will last two months before abruptly ceasing (the last one just came as a result of her just cutting communication). I’m not an asshole, I am polite and courteous. But I have no belief in my abilities to attract a woman and when I go to town now will pretty much just get drunk with friends and then a few hours later go home without talking to any cute girls. What would you recommend for a guy who has got the yips?
-Dirk Millicent

Step 1: don’t say “yips.” Also, nobody meets anyone of worth in a bar. Well, except for one friend of mine who met his future wife in a bar, but he’s tall and handsome and confident and at the time was the commander of the Marine Corps’s Silent Drill Platoon. So unless you’re on Marine recruiting posters, you’re probably not going to meet anyone while you’re drunk and desperate in a bar.

Here’s a crazy idea! How about — and I’m just spitballin’ here — instead of getting drunk and not talking to any cute girls, you try talking to some cute girls? Have a beer or two to loosen up, then walk up to an attractive woman and say, “Hi, I’m Dirk. Can I buy you a drink?” (PRO TIP: make sure her drink is empty or almost empty before walking up to her.) Offering to buy a woman a drink is especially successful in starting a conversation if you’re ahead of her in line at the bar: you’re saving her time and money, which means she’s indebted to you for her name and some amount of polite conversation. After that, it’s up to you. Ask her questions. Ask follow-up questions. Tell her that her responses are “cool” and/or “fascinating.” Like I told Mr. Softee up above: the women you find attractive aren’t special just because they’re in a low-cut top. They’re regular human beings with problems and worries who are flattered by attention (and, if they’re dressed slutty, probably really boring, too.)

In the long run, though, you’re better off meeting people through friends or kickball leagues or even the Internet.


Football: Your other questioners always give terribly boring backstories in this section.  I must know… Stafford or Cam?

I’m a little hesitant to say Cam because he has such a small sample size of fantasy success, but Stafford’s injury history forces my hand. Cam.

Sex: I need to quit drinking. Prior to the “incidents”, I had been blacking out an average of twice a week for the last 10 years. But, that was all happening at parties and bars with friends, so, not the end of the world. I recently got fired from my very high-paying job in finance, for reasons not at all related to drinking, and was given a one-year paid vacation to sit on my balls for a year due to some totally fraudulent practice called “garden leave” (lol 1%). Then, the troubles really started. Long story short, when you drink all day for multiple consecutive days, and then go cold turkey, your body misses the sweet, sweet booze, and can turn dead. I landed in the ER twice for withdrawal complications after trying to ween my body off the juice myself and going into seizures. No one in my life knows about this.


So obviously, it needs to cease. Getting back to full-time employment will help, but it isn’t the ultimate answer, as my drinking had gotten to problem levels well before the ER trips. My question to you, and the commentariat as well, is: how the fuck do you do sobriety? What do you even do on the weekends? How do you fuck random chicks? Or don’t you?  How do you fucking, well, have any fun? All I know is drinking. How do you say “water’s fine” to a waitress on a first date without seeming like a serial killer? How do you stay sober at a bar and hit on a girl without seeming like a creepy rapist? How do you stay sober at a bar, period?  If that’s not possible, then… what do you do? Find new friends?
Needs a Drink in NYC

Those are tough questions to ask of someone whose avatar has been a glass of whiskey for the last six years or so. But for as much as I celebrate drinking, I also try to stay away from its pitfalls — I never drive drunk; I don’t let it affect my work; and until this last weekend I hadn’t suffered a blackout for the better part of a decade. I guess you could say I drink in moderation excessively. But let’s address your questions one by one.

How the fuck do you do sobriety? 

I’d recommend starting one of those 12-step programs that are all the rage. Also, a proper rehab facility might help you cope with your disease. I’m guessing with these, by the way. No one has ever asked me about sobriety before. My fiancee, however, doesn’t drink, and she doesn’t seem to have a problem enjoying her life. She’s even outgoing and a lot of fun, believe it or not.

What do you even do on the weekends?

I dunno, hobbies? Carpentry, softball, kayaking, whatever passes the time and makes you feel good. A lot of recovering alcoholics become avid distance runners, because running is a relatively safe addiction that also produces a a nice little high.

How do you fuck random chicks? Or don’t you?

Craigslist, I guess. Frankly, if you’re grown up enough to say, “I need to stop drinking,” then it’s probably also time to take “fuck random chicks” off the to-do list.

How do you fucking, well, have any fun?

Dude, you live in NEW YORK CITY. Go to the best stand-up comedy scene in America (Comedy Cellar), go to the movies, play sports in the numerous urban parks, watch some Broadway shows, go to museums, ride a bike around Manhattan… ALL of those things are perfectly enjoyable without booze.

How do you say “water’s fine” on a first date without seeming like a serial killer?

You tell your date that you’ve already done a lifetime’s worth of drinking, so you don’t do it any more. And then you tell her to have whatever she wants, because it’s a long race and she needs to catch up.

Also, don’t say “water’s fine.” Ask for a seltzer with lime. Even though your date KNOWS that you’re not drinking, her subconscious will tell her that it’s a gin & tonic, and she’ll be more at ease. I know this because my fiancee did this same thing when we were dating (whether she intended it or not, that was the effect).

How do you stay sober at a bar and hit on a girl without seeming like a creepy rapist? How do you stay sober at a bar, period?

Okay, now the questions are getting out-and-out stupid. “How can I have all my faculties and talk to a drunk woman without her suspecting that I want to rape her?” Come ON. If anything, it will be easier to talk to pick up women at bars (if you’re still trying to fuck random chicks, that is), and nobody at a bar gives a shit what you’re drinking as long as you’re holding a drink in your hand. Hell, pick up an empty beer bottle, take it into the bathroom, and put some water in it. Ta-da, you don’t have to worry what other people think!

I’m not saying it will be easy. Hell, the only reason I don’t drink to excess is that I never want to get to the point that I have to give it up. There will be times when your social and even business life will be hampered by not drinking. But you’ll be healthier, remember your nights clearly, and get a clear window into how stupid you looked when you were blackout drunk. Not to get all serious on you, but I’ve met two different people who are in wheelchairs for the rest of their lives because of accidents that happened when they were drunk. In the grand scheme of things, this is a small annoyance, not a tragedy. Good luck.

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