It Takes Two To Tango, But 14 For A Real Fantasy League. It’s The KSK Sex/Fantasy Football Mailbag

05.20.10 8 years ago 98 Comments

Ufford is out this week, which means that you can forget about getting lectured on email length, or receiving any credible relationship advice. Ever notice that most of the people looking for advice aren’t really bad at something, but rather they’re just too afraid to try? Trying and failing is a big part of life, and it is an even bigger part of getting laid. The journey to a lady’s promised land begins with a single step. Unless you’re in a whorehouse in Thailand, and then it just begins with a single. And now, your emails, where I blow up on the first douchebag and do my best to exude benevolence upon all those who follow.


I have recently started dating a girl and am noticing something that’s a bit worrying.

She has a penis? Sorry, I’m still getting warmed up…

When she gives me a blowjob, it’s like, i’m numb and don’t really process the feeling or something. It almost seems she’s using too much saliva or something and not enough friction? I don’t really know, but I’ve gotten blowjobs before (as recently as a week ago from a diff chick), and they feel more enjoyable. Hers just feels like a warm wet cloth and it makes me limp out. I’m trying to get an idea what to tell her to differently, before I try to tell her to do it, so I don’t make her worry she sucks at bj’s. I thought about getting her a book on giving bj’s, but well, our 3rd date isn’t until Sunday, and that might be too fast for that sort of thing. Any thoughts?

Well, let’s recap. You’re complaining about this girl, with whom you’ve been all of two (2) dates. She apparently has so little to offer you that she has resorted to oral on the second date in order to win your affection. And she’s not doing it the way that pleases you.

And you know that it’s not your fault, because some “diff chick” played a couple slides on the pink trombone last week and you thought that went pretty well. And now you’re asking us for advice on how to coach this original person on how she can deliver in a way that you find more satisfactory. And you’re considering buying for her, a girl that you’ve probably not even bought so much as a cheese steak sandwich, a book on how she can better meet your fellatio needs? And you’d like to know our thoughts?

My thought is that you should fall into an open sewer and choke on America’s shit.

I am enjoying the Tebow articles. Seriously, i can’t wait for his future scandal to break. What do you think? Is he a homo? (i think so)

If he is, maybe he could give you decent head. Fucking asshole…



We’ll start with Fantasy Football. This isn’t a player question, but just a general fantasy football query.

Works for me.

I play in a 12 team, H2H points league. We’re all extremely competitive, and it’s a ton of fun. Last year, I finished the season 6-11, but first in the league in points, by a wide margin. How is that possible, you may ask? Simply put, for the first eight weeks of the season, every team I faced had a career week. I’d lose 148-140, and then the team that beat me would put up 90-100 point weeks after that. Never have I felt so unlucky in fantasy football.

It happens to lots of guys.

So, my question is, why do leagues continue to use H2H matchups? I had a solid roster (AP, Welker, Rivers, Favre at flex), and would have killed in the playoffs (we mirror our playoffs with the NFL playoffs; there’s a whole re-draft process that isn’t worth getting into). But because of those “career weeks” I faced, I had no chance. What’s your preferred league setup?

Head-to-head is the only way to do fantasy football, and unless you’re starting up another boy band, don’t ever use “H2H” ever again. Just looking at it makes me feel gay. In the bad way. This will happen a lot when you’re in a 12-team league, because the talent is more evenly distributed, which means more of your games will be left in the hands of variance. Put me on the record as being anti-12-team. Their outcomes are totally arbitrary. Next year it’ll be some other whiny bastard in your league getting everyone else’s best shot. Now is a good time to prepare funny, demeaning things to say to that person. Consider your current strife to be your inspiration.

On to sex. Not really a question, just some general advice. My girlfriend and I love sex; I mean love having sex. For me, I find it difficult to…ahem…”finish” with a condom. I don’t complain, I don’t bitch. But after two weeks, I finally said something to my girlfriend, and she and I have been able to work out alternate arrangements. She won’t budge on the condom issue (and I haven’t pressured her to do so, because that’s a dick move). But, after sex, she pops it off and goes to town. The point of this is that I see so many questions in the mailbag that could easily be solved if both people just talk about the problem. Why is this so hard?

Here’s one opinion. It’s hard because we want sex to be perfect. We want it to be great every time. We want to look great and smell great and the other person to not complain about the handcuffs digging into her wrists. Sex has long been purported as a leading indicator in the health of a relationship, and rightfully so. When the sex starts to dry up, the relationship tends to follow suit. When you’re laying on top of your partner in a fit of sweaty, naked coitus, your shaky trust and communication issues have nowhere to hide.


Sure, man.


Dear Masters of Telling people to nut up or shut up,

You may remember me as the lucky bastard who had a Domincan beauty way out of his league interested in him only to be foiled by the language barrier and the fear of the older gentleman who lives in her apartment.

Let’s say that we do [second item]

I learned how to ask who he was, he is her uncle. Things aren’t too shabby, she thinks I am cute, she thinks its cute I am learning Spanish just so I can talk to her, She likes my cooking and she tolerates my ganja smoking which she partakes from time to time. Oh and she calls me Papi in bed which is just like goddam catnip. We hang out pretty frequently, I might even go so far as to say we are dating. My Spanish still blows but between my learning Spanish and teaching her English we can communicate using broken sentences and lots of gesturing.

Hey, prick? I’m not hearing a problem in any of this.

Anyways, I figured I should have a question and here was all I came up with. I found out the other day when I went next door to see if she was home that she wears glasses. I love glasses, I think they are one of the sexiest things a woman can wear.

I know what you mean. I used to be an optometrist’s assistant before I got fired for masturbating to a Luxottica poster.

She thinks they are ugly, and whenever I try to tell her I like them, she thinks I am making fun of her and/or her specs. Any advice? Also feel free to use this question as an opportunity to publicly make fun of me for trying to gild the lily.

Your quest for unnecessary adornments aside, it’s my experience that you can’t force a mindset onto a woman. About anything. If she thinks XYZ makes her look fat/ugly/unable to be taken seriously at the office, then perception is reality. And yet we let these people vote! That’s a joke, ladies. You know that we’re crazy too, only for much more time-honored and awesome reasons.

Anyway, your best play here is to make one more solid push and then drop it. Plan a dinner date and suggest that she wear her glasses there. It would help if the menus at the restaurant had very small type (and, from the sound of things, in Spanish) Give yourself a forum to express yourself that she’ll take as being sincere. Even if that push fails, you might get a comment six weeks later to the effect of, “Do you really think these look good on me?” Plant the seed, brutha. Plant the seed.


Dearest Pussy Pundits,

Hey, don’t forget Kogod! Sorry, Maj. That’s just a little pussy pundit humor.

Sex:. I’m 30 years old, had my ass handed to me by my only serious girlfriend about three years ago after she declined my marriage proposal SIX YEARS into the relationship.

WOW. Six years and she shot you down?! I’ve never heard of that before.

We tried to remain friends because of an unusually large circle of

Hang on a second. You. Dated her. For six years. You proposed. And she…she said no? That’s unreal. And brutal. Brutal and unreal. I honestly don’t know how I would react to that. It would probably involve a chainsaw and a few dead convenience store workers, though. Anyway, sorry to interrupt.

We tried to remain friends because of an unusually large circle of tight friends, but ultimately I gave up on that about six months ago. Dating was not agreeing with me for the past three years since the split.

Seriously, that is horrible. I feel terrible for you. See? I can be nice!

About a month ago, I met a beautiful young woman age 26, two kids from a previous marriage that ended last year. We’ve been dating for rather casually since then, the sex is great, we enjoy being around each other, we have mutual friends, interests, etc. etc. I haven’t met her kids yet, and she’s been pretty keen on moving slowly on that front, which is fine by me, however…

/puts on Hurt Locker bomb squad outfit

During the past month I was away on business when I met another friend of a friend who I got along famously with. She’s 25, doesn’t have kids, is adorable but slightly less attractive, and has my identical sense of humor. I’m sure you can tell where this is going.

Sorry, I’m still putting on my bomb suit. I hate breaking in new pants.

Both potential relationships could be fatally flawed (long distance, maybe not ready to be the father of someone else’s kids), I’m just not sure which one to pursue. When I returned home, I figured I would just casually go with the flow assuming an answer would present itself. Instead it’s just gotten cloudier.. I see the potential for something meaningful with both women, but I also see a recipe for disaster…

Difficult to see. Always in motion is the future…

So do I press to move things forward faster with the one in town, or try and make the long distance thing work with someone I may be better matched with?

Let me start by saying something that’s not at all helpful.

I’m sure that both of these women are wonderful people, but I personally hate both of these types of relationships for different reasons. When a guy dates a woman that already has kids, that guy has to realize up front that he’s never going to be the most important person in that woman’s life. And I can’t fault that mindset at all. If I had kids and I was dating, I’m pretty sure my type would be another weekly paycheck wearing red pumps. You’ve probably figured out a lot of this already. Like I said: not helpful.

And somehow, long distance might even be worse, because you share even less with that person. Most of it is phone calls and IMs and the occasional happy-faced rendezvous in alternating cities. That’s nice, but that’s not a relationship. If you’re looking to build something meaningful with someone, stick with the person in your own backyard. You know, the one you’re already having sex with.

By the way, how stretched out is it? I’ve always wondered.

Football: Doesn’t it seem like every couple of years there’s a team that makes a lot of flashy off season moves, gets predicted to make the super bowl and then subsequently shits the bed? Are the Jets the new Redskins?

Eric Mangini had a lot of success in his first year as Jets coach. After winning the division in 2006, he stood pat in the offseason and went 4-12 the following year. Most of the Jets’ moves this offseason have been relatively sound, and indicate that they won’t be resting on their laurels this fall, and they need to stay busy if they want to keep selling those PSLs and season tickets. But I see your point. Cutting Alan Faneca when he’s owed $5 million in guaranteed money this year seems a little nuts.


No time to make up a bullshit header.

No time to reply to your jizz-swallowing email. Ah, I’m just kidding.

Football first.
For the past 4 years I have ran a fantasy football league that consists of my friends

Actually, I wasn’t kidding. Fuck you.

Ladies First: I am 23 years old and just graduated college last year and moved to Chicago.

Very cool. I’m going to be in Chicago in three weeks. Can I sleep on your couch that Friday?

Needless to say, the dating scene is a little different in the real world. I have never dated an older woman but recently met a 27 year old yoga instructor that I think is into me and the vice versa.

Yoga instructor? Excuse me for just a second.

/unzips pants

She has a great personality

/zips pants back up

and better physical features.

//keeps pants zipped up

We’ve gone out for dinner twice. I kissed her following the second dinner. Having never been with a woman 4 years my senior, let alone one, I have no idea what to expect psychologically from her. Any big differences I should be considering? Seeing as how its been two dinners and I have yet to make a serious advance sexually, where do I stand now and any tips on fixing this? I need work on making moves, particularly while sober.

You just touched on a good point there. It’s better to be sober and nervous than to be drunk and charming. Because drunk really isn’t charming in real life as it is in college. I’ve been out of college for a while, and I still occasionally act in defiance of this principle. But that’s really how it is.

So number one is don’t get drunk. Number two? Well, I need more info. Are you going back to her place and just watching TV? She’s going back to yours? This should be happening after two dinners. One person sits on the couch while the other person (the host) pours a couple drinks (this is why you shouldn’t be drunk). You take the drink. You make a nice toast (“To yoga!” or some shit). You take a drink. You smile. You say, “I just love being around you.” And then as you move in for a gentle kiss, hold your index and middle fingers together on your free hand and jam them into her pussy as fast as you can.

It helps if your apartment is clean.

On a related note, I am struggling to find mutually enjoyable things we can do together besides eat. Movies are a little cliche, and I don’t think there is a ton of crossover with interests besides exercise in general. She has mentioned biking and I’d like that but I was wondering if you could help me with some ideas for fairly original/inexpensive things to do with a 27 year old girl.

I have a lot of ideas. Unfortunately, none of them involve living in Chicago. Okay, being helpful here…you’re new to the city. You should ask her to show you the sights. It’s getting warmer outside–go to a park. Ask for a “private yoga lesson.” Actually, don’t. She’s probably heard that 100 times.

Onto Business: I am the commissioner for a league of long time high school friends. We are going on 7 years now and currently have 11 remaining original members.

Color me impressed.

One guy dropped (read: forced) out in season 3 due to lack of participation. The last couple of years we have tried to find some subs and its gone less than stellar. Last year in particular we had a friend of a friend join. He didn’t show up for the draft, made a few picks via phone, didn’t pay, and went 0-13. So this year, I’ve asked the original 12thmember if he would come back. He agreed, so we have the whole crew back.

Oooh, I smell trouble brewing! Wait, that’s just me.

However, I gave a league member the go ahead awhile back to ask one of our mutual friends if he wanted to join. I know this kid personally so I knew he wouldn’t be a bust like the guy last year. After awhile I hadn’t heard back so I asked the original member, only to hear a few days later mutual friend said yes and is esctatic. How do I handle this tactfully? Keep season 3 member or mutual friend?

Well, you’ve already made your decision. I don’t know how long ago “awhile back” is, but it sounds like your acquaintance is just a few days too late. This is what happens when you miscommunicate (which should and does include “not communicating in a timely fashion”). This is a good reason to have one guy handle filling vacancies in your league.

That said, do you have any hope of bringing in a 14th guy? It would make your league a lot less gay.

Also, the quality of our league posts has been dogshit for a few years now. How do I bring back the fun in posting? I liked the idea of AB a few weeks ago about having the lowest score each week having to recap (in Sex Machines and Seahawks) but that could become problematic because those who get the lowest scores are typically the most apathetic. Any thoughts are greatly appreciated.

I don’t see the point in forcing the worst player in your league to do the recap. That guy sucks. Why would I want to read his takes on fantasy? Doing the blog post should be a reward, and an opportunity to call out all of the dipshits that stood in his way. Fantasy football league posts should be shit-talking, a couple stats, maybe a picture of a panda, and that’s it. And those posts should be fronted by someone that gives a rat’s ass, with all league members contributing in some way.

But seriously, how comfortable is your couch?


Sex… erm, well, not exactly. About 6 months ago, my 6-year relationship with my college girlfriend ended in fiery wreckage (I’ll skip the details, though they’d be great for another mailbag entry).

Not to make light, but I wish I had a joke for “fiery wreckage,” but it’s too close to lunchtime. Anyway…

The breakup has been tough, but I’ve been trying to move on and get back on the horse. Over the past couple months I’ve gone on a couple dates (thanks, internet dating!) but nothing of substance… until now. I’ve met a cute girl who’s definitely interested in me – we’ve gone on dates the past two weekends, including watching a movie at her place last weekend, and she’s made it very clear that she wants to see me again (we’re doing dinner and a movie tomorrow), even though we’ve not had even the remotest romantic/physical interaction.

Patient broad you got there…

I share many of [Ufford’s] thoughts about gentlemanly courtship – my basic approach toward women and dating is to be genuinely friendly, interested, conversational/engaged, affable, etc. I think this approach helps me get women’s interest, such as in the current case, and I enjoy their company. However, I don’t know how to parlay it into a romantic encounter. It’s not helping that my skills in this area are so damn rusty, nor that I’ve always been a serial monogamist and not a ladies’ man.

“I’m so terrible at seducing women, because it’s been so long since I never tried!”

I’m not saying that I want to start having one night stands, but a makeout session and trying to steal second (head first… like Pete Rose), laying the foundation for more in the future, would be nice. For instance, I can’t help but get the feeling that having me over last weekend as a not-so-subtle invitation for some sexy-time, which I completely squandered – we had a great time and she wants to see me again, but all we did was talk and watch the movie.

You really need to learn how to take the next step while still being a fun and sociable date.

So, I guess my question is: How I can take the next step while still being a fun, sociable date, especially if she wants me to initiate (which I think she does)? I know this should be easier than I’m making it.

This is what I like to do. I like to get dinner, and then tell her that we have tickets to some event. Only…you don’t. So after dinner, you go, “Oh, crap, I left an item pertinent to this event in my apartment.” So you both go to your apartment. Since you have no clue how this works, I’ll continue.

You both walk in and you offer her a drink. She sits on the couch. You pour. She takes the drink. You make a nice toast (“To yoga!” maybe). You take a drink. She takes a drink. You smile. You say, “You’re just so much fun to be with.” And then as you move in for a liplock, reach behind her head with her free hand and yank the shit out of her hair while screaming “GIMME THE FUCKING LAUNCH CODES NOW!”

It helps if your apartment is clean.

Football: I don’t play FF, but I am a Bills fan. I don’t really have a question, but I can’t help but feel that all the hate for Marshawn Lynch/BEEF MOE from the fans has a slight racist tinge. Thanks for running out of town a star athlete and the only player on the team who was lovably insane, rednecks.

“He totally would have stayed here if it wasn’t for all of those mean things you guys said!” You just know that Marshawn was dying to run through a brick wall for…

/checks Wikipedia

…Chan Gailey.


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