People In Their 20s Make Me Feel Old: The KSK Sex & Fantasy Football Mailbag

05.03.12 5 years ago 102 Comments

After a week off due to NFL Draft festivities, the mailbag is back. As such, some of the following questions date back to before the draft, so be nice to the people who write as though the draft has yet to happen. Being mean is my job.

Just kidding, I’m not mean. Merely old and grumpy and direct — and unwilling to publish submissions that are 1000 words long. ONE THOUSAND WORDS! Don’t do that to yourselves, people. Don’t write all those words just for me to say to myself, “This is an interesting problem, but good God I can’t possibly include this because nobody is going to read it.” Please: edit your ish before you hit send.

On to your questions!

Slinger of Seahawks Swag,
Now that it’s obvious that RGIII is going to the Skins, what’s a reasonable spot to draft him. Is he sixth round material?

Ladies and gentlemen: Redskins fans.

No, I don’t think RG3 is worth a 6th-round pick in fantasy drafts. I don’t trust any rookie quarterback to be a quality fantasy player, and the only person to disprove this theory, ever, is Cam Newton.

But for the sake of argument, let’s say RG3 and Newton have the same abilities and potential. Last year, the Panthers had a relatively solid offensive line, two quality running backs, and a star receiver in Steve Smith. The Redskins just let go of their best receiver, Jabar Gaffney, who is not the kind of player who should be a team’s best receiver. As much talent as RG3 has, I don’t think he has the players around him to bet on him being a fantasy success. If you want to make him a homer pick, get him in the 12th or 13th round.

If that FF question wasn’t good enough, here’s early 2000s Elizabeth Hurley.

That brings back fond memories of the first Austin Powers, when Hurley was the hottest woman on the planet and Mike Myers was funny.

Secondly, not sex but love. Ish.

I met a girl a month ago and thought she could be the one. I took her out a few days later. The first words she said to me were “You need to know I accepted a job in San Francisco. I leave in three weeks.” So naturally, I fell in love with her. 

She’s a whiskey-swilling, hard-partying hot ass girl. Now all I can think about is how miserable I’ll be when she leaves town tomorrow. I haven’t told her I want to move, but I totally would (San Fran’s the best city in America). I think she’s perfect, but how how do I separate my true feelings versus what may just be an emotional experience regarding “lost opportunity.” Also, how does one attempt to handle a casual long-distance half-relationship and make it grow into something larger. And, am I being ridiculous? She hasn’t met my dog and when my sister asked what I liked about her I responded “She drinks rye on the rocks.” Am I just smitten?

Short answer: yes, you are smitten, and you’d benefit from some time, patience, and perspective.

But the short answer never suffices, does it? There’s nothing wrong with being smitten or infatuated at the beginning of a relationship (which is what I’m calling your fling, for lack of a better word). In this case, your honeymoon phase — which is perfectly normal and the best part of a new relationship — is likely intensified by knowing that you’re losing Ryelene McPartypants just as you’re getting to know her. It romanticizes the time you have together and causes you to be nostalgic for the moments you share as you have them. Nostalgia is always a problematic emotion, but it’s especially bad without perspective.

So stay in touch with her — Facebook and Skype and Gchat make that easier now than any other time in human history — and if she still digs you from afar, go visit her in San Francisco. If the visits go well and you develop an emotional connection beyond “I swear this whiskey-drinkin’ broad has a microwave in her pussy!”, then hey: maybe you should look for a job in San Francisco. Focus on making smart decisions about YOUR life independent of love, and if she returns the feelings and fits into your life, bully for you.

And finally, because I’m a wet blanket: keep in mind her warning when she met you. Hard-partying girls who are incredibly charming are very easy to fall in love with, but very rarely “the one.”

(Also of note: the term “the one” forever annoys me. Unless you are a miserable asshole, you can fall in love and enjoy a long and healthy partnership with innumerable people on the planet.)


Football: I’m in an extremely competitive and active 12-team Fantasy football league. We all love this league, but the only problem is the Commissioner sometimes has a bit of an ego. For the last two years, a buddy and I have been leading a rallying cry to switch our league to decimal scoring. Right now, we’re using whole numbers so, for instance, 9 rushing yards = 0 points and 10 = 1. The rest of the league is either with us or indifferent but the Commish will hear none of it and trots out some really lame excuses like “it doesn’t look like a real football score” (because 130-119 totally does). How can we reason with him? Is there any reason not to use fractional points? My buddy and I have gone so far as to consider forming a new league with decimal points that we’d co-chair but we’re afraid this would splinter our league—which, again, rocks—irreparably.

I prefer decimal scoring simply because it’s more accurate. Why have a round number that approximates how your players performed when you can have a better, more accurate representation? The argument against decimals is like an argument against instant replay: “DURRR THIS IS HOW WE’VE ALWAYS DONE IT AND I LIKE IT.” It hinges on aesthetics rather than reason, and as a sentient being capable of critical analysis, that irks me.

That said, I’ve been in a league that used integers, and it was still perfectly fun. It’s not something that’s worth blowing up your fantasy league over.

Sex: I just moved to a new city a few months ago and decided to take my chances with online dating. After a few lousy dates I met this cute girl and we hit it off. We started seeing each other a few times a week, hooking up frequently, texting a fair amount… all things that would signify the start of a casual relationship. Then, about a month in, she rather abruptly broke it off, saying she wasn’t “looking for anything” and that we’d be “better off as friends.” I was bummed but handled it with class and told her I understood. (I didn’t.) About a week later, she starts texting me again and warns me that if we did ever meet up again she might try to make something happen physically. This sets off a conversation where she confesses that she thinks she made a mistake; that she misses me and doesn’t just miss the attention or the sex and wants to see me again.

I like this girl. She’s not the MOST attractive girl I’ve ever hooked up with but I’m attracted to her nonetheless and the sex is good. She’s funny and intelligent and apart from the whole breakup-out-of-the-blue thing, seems to have her shit together. Am I stupid for taking her back? I’m 24 and in a big city and feel like I would certainly have other options, but again, I like her and like having sex with her and she seems to be very honestly apologetic and ready to start a relationship. (Obviously, if she waffles again, she’s gone.)
BSJ, 1.0st time emailer

Ahhhh, online dating: where both men and women can see a whole bunch of people at the same time, prioritize who they like, break things off with someone they like but isn’t at the top of their list, then get ditched by the person at the top of their list and experience dumper’s remorse. I’m not saying that’s what happened to you, but it IS my working hypothesis.

You seem to have a pretty good handle on it, though, so go forth and enjoy the good sex.


Captain Caveman,
FF: I play in a 12 team league that turned into a keeper league last season. This year is the first time we are keeping. I can take up to 3 keepers but will lose a pick 2 rounds higher. My main options are Mike Wallace, (3rd), Ryan Matthews (got him in the 4th), Gronk (5th), Sproles (13th). Is wallace worth a 1st rounder? Im leaning towards gronk and sproles but how many should i keep and who?

Gronk and Sproles. That’s it.

Sex: I am about to graduate from college and have been with my girlfriend since pretty much the 2nd week. (yes, yes i know, didnt spread my seed around, missed opportunity blah blah). I am wholly committed and totally in love with this girl, and she is with me. Problem is recently we’ve been fighting a lot over lots of pointless stupid shit. Shes just started a job that works 9-5 and we only get to see each other in the evenings. Due to the fighting we’ve stopped having sex and a lot of things are starting to pile up.

Ive also had female attention from a few of my teams cheerleaders who i get along with like a house on fire, and flirt occasionally with. Drunkenly they have both admitted theyd like to jump my bones but i have stayed away and been faithful. I really care about her but am starting to wonder if its worth all the hassle and whether i should enjoy my last semester at college. Have i grown up too soon?
Cheers, confused small town footballer.

First of all, no: you have not grown up too soon. Grown-ups have jobs and spend two weeks doing their taxes and worry about their cholesterol. They  do not have drunk cheerleaders trying to fuck them.

I won’t discount your love for your girlfriend, but I also won’t discount that you’ve spent thee-plus years of formative emotional and sexual development with the same person, even though it runs counter to what everyone says you should do in college. But if the two of you are as in love as you say, then you need to do what grown-ups who are in love do: communicate like adults and work out the problems.

Again, I tend to be unsentimental because I’m old and all too aware of how immature I was at 22 (even though I thought I knew everything about girls and love back then), but if I had a choice between sex with college cheerleaders and no sex plus fighting over pointless stupid shit, I would choose the cheerleaders 11 million times out of ten. But don’t take my word for it, I’m just a crusty 30-something who would want to enjoy his final semester at college.


Dear Dukes of Docking,
Football: Last year was my first year playing in an auction league with some friends from college. I rode Breesus and Shady McCoy to the best record in the league and all the way to the championship before my entire team decided not to show up. Annoyed as I was at losing out on the top spot, I am debating going after both of them again. Shady is a no brainer, but I am concerned about Breesus. I got him at a steal for $25 last year (we have $200 to start), and I figure with everything going on with the Saints I should be able to get him around there again even though he was so amazing last year. Do you think he is still worth targeting or has Bounty Gate, losing his head coach and play caller, not getting a new contract and refusing to sign his franchise tag made Breesus worth less?

I think Brees will still be really good. All the hoopla surrounding the Saints should devalue him a bit, but he’s still the same player with all the same players around him. It’s probably reasonable to expect some regression (you can’t break the passing yardage mark every year), but he’s still going to be one of the best quarterbacks in the league.

Sex: A friend of mine posed a challenge. We would go from massage parlor to massage parlor, where I would get a happy ending at each. The only down time would be the drive from place to place. It ends whenever I give up, either from chafing or just plain hating myself from disgust. He thinks I’d get at least one in, and I doubt I could even do that. But I was wondering how many you think you could get done (from before you got engaged of course)?
Old Fashioned Fan

First, allow me to say that I’ve never been to an Asian massage parlor that offers this service, I don’t know where to find one, and I wouldn’t know the protocol to ask for a happy ending if I were to find myself in such an establishment. This isn’t due to any sort of moral uprightness on my part; I was simply never introduced to that particular skeezy-but-orgasmic world.

Indeed, the tactile intimacy and increased blood flow that result from a massage have definitely left me open to the idea of a handjob from a perfect stranger, but alas: it was never meant to be for yours truly.

ANYWAY. Let’s answer your question. I’m no longer in my teens, and thus I can no longer ejaculate every 30 minutes. But assuming that every happy ending is preceded by a 60-minute full-body massage and administered by a skilled and determined young Asian woman, I think I could go three rounds. After that, the only thing I’d be good for is a long nap.

(Chafing is a non-issue because masseuses have plenty of lotion, and I don’t understand your disgust. I mean, I understand it, but I don’t have the energy to pretend to have moral objections to paying for a handjob.)


To the most trusted name in football and sexual advice,
Do you have a general philosophy on when, after you start dating someone, it is no longer a good idea to continue to see other people? When is the right time to pull the ripcord on fuck buddies?

Background you don’t care about but will certainly up your word count: I’ve been dating a girl for about 8 weeks,

It is no longer a good idea to continue to see other people.

and things are going great, but it was pretty casual. We hadn’t had any sort of relationship talk and just enjoyed our time together when we could. However, a week ago a friend and occasional fuck buddy sent me a gchat saying “I’ll be in town for a conference in a couple weeks and I’m DTF” which is a term I didn’t realize people over 22 actually used.

I dunno, I think that kind of directness is refreshing. “Hey, if you’re available, let’s fuck.” (Worth noting: clear communication is one of my biggest turn-ons.)

I originally made plans but then that guilt and morality and conscience kicked in and started to think this would be bad. So I crowd sourced the dilemma to my friends who gave some varied answers:

1. It’s time to stop sleeping with anyone else when you would realistically be upset to find out she was doing the same.


2. It’s time to stop sleeping with anyone else when traditional Friday/Saturday date nights are assumed, going from “do you want to go out” to “what are we doing this weekend?”


3. It’s time to stop sleeping with anyone else when you refer to each other as boyfriend and girlfriend to your friends.

No shit.

4. It’s time to stop sleeping with anyone else when you have the explicit talk about formalizing the relationship.


Now it’s not relevant because all of those are true now and I had to cancel on DTF girl (by being honest, since she is also a friend), but the question has stuck with me for a while and I’d really like more opinions on this.

The answer to your question is “All of the above, plus plenty of other scenarios, too.” (I’m not such a prude as to say, “You can only sleep with one person and you must end things with that person before sleeping with the next person,” but I’m also old enough to be all, “BE CAREFUL KIDS! USE A CONDOM EVERY TIME!!!”)

Don’t overthink this. If you have to wonder, “Wait, should I be sleeping with another person?” the answer is probably no.


Football First: I won my fourteen team keeper league last year, which means I am picking on the turn this year. I already know one of my keepers is going to be Cam Newton for a 14th rounder, but I’m having some trouble with my other keeper though. Which of the following players should I hold on to: Megatron (lose first round pick), Ryan Matthews (lose fifth round pick), Gronk (lose an 8th round pick). Standard scoring with an additional .5 PPR.

Gronk. Megatron’s worth a 1st-rounder, but Gronk’s the better value.

Also: it is obvious why you won your fantasy league.

Sex/Relationship Stuff: I’ve been dating a terrific girl for about 5 years now. We met during my Junior year of college, and ended up moving to the same city after school. She’s beautiful, funny, sane, and our families love each other. As recently as earlier this year I had a frank conversation with my older brother about how I could see myself proposing to this girl. But something has happened recently (it started maybe 2-3 weeks ago), and I have found myself completely turned off by her for some reason. I still enjoy being around her and I still care for her immensely, but that sexual electricity has gone away for some reason. Nothing has dramatically changed in our relationship or in my life, I can’t figure out why all of a sudden I find myself completely disinterested in her physically.

I’ve had the occasional time over the past 5 years when maybe I wasn’t feeling up for sex, but it never lasted this long. I’ve been basically forcing myself to sleep with her just as not to alarm her while I figure this stuff out. I suppose my question is just whether these sort of lulls are normal, or if this is indicative of a larger problem that I need to address with her. Also if I am going to address it with her, how do I have that conversation in a tactful way so it just doesn’t sound like I’m saying, “I haven’t been attracted to you for a while and I don’t know why.”
Bombs Over Boston

I have no idea. I mean, no relationship has fireworks that last forever, but if you’re straight-up turned OFF by her, it’s indicative of a larger problem — and I don’t have the information to identify it. Are you not interested in sex with anyone – or just her? If it’s the former, then the problem is in your head, and some combination of a therapist and urologist can probably solve your problem. If you’re turned off by your girlfriend but find other women attractive, then something in your relationship has changed, and you need to identify it before confronting her about it. Good luck.


Dear Brighteners of my Otherwise Dreary Workday,
I’m writing in to obtain your guidance on how I should best proceed with regard to a very close female friend.

“I need help with a close female friend.” –Someone less long-winded

We’re both in our late 20’s and have been close for over 10 years. She’s a great girl who just so happens to be gorgeous. Way back when we first met in high school, she had a boyfriend and I was single. After a month or two of hanging out, she professed to having feelings for me to the point of considering breaking up with her then-boyfriend to start dating me. I decided not to pursue things romantically with her until she was single even though I had strong feelings for her. She stayed in that relationship for another year or so until just after I graduated and moved away for college.

During our college years and after, there were many factors that contributed to us remaining just friends (each of us had long-term relationships & a few hours of driving between us). Presently, she lives far away, but will be moving near me soon. That’s great, except for the minor issue that she has a live-in boyfriend that she’s been with for a few years.

Tough shit for you. Time to move on with your life.

I’ve never told her how I felt because we’ve never been in a position for it to really lead anywhere anyway and for fear of what it could do to our friendship. I suppose those same reasons for not saying anything apply now, but I’m getting to a point where I want to let her know how I feel instead of taking it to my grave. Everyone who’s known us throughout the years thinks we’d be a perfect match and there’s a history of mutual attraction despite it never leading anywhere physically for the aforementioned reasons.

“You guys would be perfect together!” This has been said by billions of friends throughout human history, many of whom have an emotional connection to Jennifer Aniston because of US Weekly’s coverage of her relationships since Brad Pitt left her for Angelina Jolie. Which is to say: your friends are probably great; they may also be morons.

I’m sympathetic to your plight: timing can be a real bitch. But let’s be real: if she REALLY wanted to be with you, she would have made sure to be single in the same place as you some time in the last ten years. If she desired you as much as you suspect, she would have broken up with that boyfriend of ten years ago before you went to college, or arranged to visit you sometime when you were both single. She didn’t — and you didn’t. Ergo: this is not a love that is meant to be, but a super-boring version of a novel written by a Brontë sister.

Should I risk messing with her head, complicating her current relationship and damaging our friendship to lay all my cards out on the table or am I better off keeping this to myself and continuing to be respectful of her current relationship as I have been up to this point? Is there a way to deliver my message with some tact so it’s more of an implication rather than a full-on declaration of my feelings for her?
Free Frogurt Enthusiast

Do yourself a favor: tell this girl that you don’t think you can be friends any more because you’re not interested in her friendship without a romantic component. Not only is it what you should have said ten years ago, but it will force your life forward in one direction or the other. Either she’ll decide that she wants you back and you can finally resolve this proto-Victorian melodrama, or she’ll be super-sad to not see you any more and you can move on with your life and date someone who’s, I don’t know, ACTUALLY AVAILABLE.

I’ve said this time and again in the mailbag, but when you want someone else to want you, the best thing you can do is to say, in essence, “You can’t have my time and affection any more.” That makes them feel rejected, which makes them want you. (And if it doesn’t work, you get to walk away with a clean break, knowing that you handled something like a BAWSE. Win-win every time.)


Master Chief Muff Diver-
Fantasy First-
What do you think of Michael Floyd as a late round flier? I figure with Fitzy being the golden god that he is, he’s going to command a lot of double teams, and barring any Crabtreesque contract clusterfuck, Floyd should be the #2. I am just worried about the QB situation out there. Thoughts?

Agreed. The quarterback situation is less than ideal, but a talented rookie WR behind a star receiver has been a good bet in recent years. Julio Jones had a pretty stellar season in a similar position last year, and before that Dez Bryant did relatively well as the #2 receiving threat. I should probably look up some other cases to back up that opinion, but… eh.

Ham Glazing-
I’ll try to make this, uh, brief.
I started seeing a girl about a month ago and things have been going pretty well. She’s smart, funny, great conversationalist, has an amazing body, and is an absolute fucking firestarter in bed.

Things are pretty great. I don’t know if she’s a keeper yet, but I’ll worry about crossing that bridge when I get to it.

“She’s completely ideal in every way, but I’m not sure if she’s a keeper.” –Someone in his early 20s, who will probably meet a comic book-reading bisexual Brazilian supermodel any day now

Heres the catch- I am in my first year of law school and with finals coming right around the corner, I have devolved into a sleep deprived, over-caffeinated, tweaked out shell of a human being. I have been studying for about 20 hours a day, I get no sleep whatsoever, and my life is a living hell.

While she knows that I am going to be slowly killing myself for the next two weeks or so, the prospect of us not spending much time (any) together is not sitting well with her. She’s been hammering me constantly about not hanging out and is always calling me at awful hours to try to hook up. Granted, under normal circumstances the latter would be pretty goddamned sweet, but I don’t really have the time or the energy right now to be her booty call (furthermore, the odds of me even getting it up are virtually nil, given the absurd amount of amphetamines flowing through my bloodstream).

What would be the best way to tell her that I need some SERIOUS me time right now (preferably without driving her away)? I like this girl, I would like to see where things go with her, and I’d rather not have to climb on the ol’ “get blacked out drunk and wake up in a stranger’s bed” horse once finals ends, but I got fucking responsibilities that take precedent.
Guide me with your wisdom, O Prince of Poontang,
-Tebow’s Circumcised Lover

Why are you studying so hard? So you can get ahead of two people in your law class and maybe beat someone out for an internship that hopefully leads to one of the dwindling jobs in the law profession, a suffocating indentured servitude that crushes the spirits of talented, competitive people?

Take a day off from the uppers, spend half of a day getting laid by this horny girl with an amazing body. Afterward, when you’re all sweaty and overloaded with endorphins, establish some boundaries. Tell her that you’ll take a half-hour break every day to talk to her, but that she should be prepared for you to be a little preoccupied mentally for the next two weeks — at which time, you want to take her out for a nice date to celebrate this mess being over. Something like that: set up boundaries, but don’t be as rigid as you are now. When you look back on your life, you’ll appreciate the times you had hot sex a lot more than the hours you spent studying.

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