‘How Can I Get Better At Kissing?’: The KSK Sex/Fantasy Football Mailbag

04.15.10 7 years ago 82 Comments

Unlike one of our emailers, this guy didn’t meet his girlfriend at church.

I love you readers. You know that, right? I love you. I sincerely care about your problems, and I want to help. But, you know, sometimes you make it difficult. For example, when I explicitly state that a 700-word email is too long to print in the mailbag, that is NOT an invitation to submit a 1,283-word email. I simply can’t publish that. People’s eyes will glaze over. Even if you have some very sad circumstances and happen to be a disabled veteran, the only thing you accomplish with something that long is making me feel guilty for excluding your letter.

Please. Help me help you.

Anyway, this edition of the mailbag runs a mere 2796 words, which is a little thinner than some of you might like. That’s life for ya.

Howdy, Caveman (or random other person who is filling in for the Cap’n)
Football first — I’ve been the commish of a 12 person fantasy football league for about 10 years. We’ve had steady membership throughout the years, and we’re all pretty good friends. Lately, we’ve talked about the idea of switching to a dynasty league. I love the idea — I dig that the draft is almost all rookies, and owners are rewarded for figuring out which prospects will ultimately make good professionals. The problem is that one owner doesn’t want to make the switch. We decided long ago that we wouldn’t change anything about the league unless everyone agreed. His reasoning is pretty solid — he was in a dynasty league a few years back that ended up having a juggernaut of a team that won the league for 3 straight years, and nobody else could compete. I’ve suggested trying the dynasty format with a kill-switch option after 3 years. He still won’t budge. At this point, I think we’re forced into staying status quo, but was wondering if you had any sage wisdom or ideas that could sway my friend to try the dynasty league.

Nope. I’ve got your friend’s back here. He’s already tried a dynasty league and hated it. And look at your meager enticement to him: a kill-switch option after three years. “Hey, c’mon man, it’s only three years of something you don’t like, even though that’s the same amount of time you spent hating your previous dynasty league.” What you’ve got is a fantasy football version of 12 Angry Men. I hope your friend makes a good Henry Fonda.

Now, I’m not saying a dynasty league wouldn’t be fun, but this insistence on tinkering with what works is the same kind of habit that makes casual drug users full-blown addicts. “I enjoy smoking pot, but I bet it’s even better when laced with acid!” “Drinking sure is fun, but it’s even more fun after I’ve taken three Percocet!” “Why no, I’ve never tried an 8-ball, but I’ve always wanted to.”

Fantasy football is FUN. It’s already fun. It will be fun again next season. Don’t get too caught up changing what works.

Sex – Well, not really sex, but dating. I’m soon to be 34, and very much single. Unlike many that write in, I’m quite happy being single. I date when the mood strikes, but at this point have no desire for a serious relationship or children. I assume that when I meet the right girl, I’ll change my mind on this. My issue comes from my friends. All, and I mean all of my friends are married, and most have kids. I’m fine with this, but as I’m sure you can guess, I find myself spending less and less time with said friends. They frequently have ‘couples outings’ from which I’m excluded. I’m not upset with my friends for this, but I feel like I’m drifting away from my friends because I don’t have a girlfriend. I’ve tried the 3rd/5th/7th/9th wheel thing, but it doesn’t really work for me. In fact, the only time we’re all together is during the previously mentioned fantasy league. My question is whether I should start dating a girl just to spend more time with my friends. I realize this would be very unfair to this hypothetical girl, but I just don’t see other options. Any advice?

Hmmmm… I keep looking for some other response besides “Tough titty,” but that’s all that comes to mind.

The short answer is “DUH. No, you don’t date someone so you can hang out with friends.” The long answer has to do with the nature of life, growing older, and accepting change. You know how often I see my best friends? Once a year, if I’m lucky. I recommend a large dose of “suck it up.”

Dear Punching Bags of douchenozzle commenters:

Sex: My neighbor is a lovely young Puerto Rican lady, who doesn’t speak a lick of English. But she is sexy as hell.


She looks young (old enough to be legal but probably at most 22, I am 29). One night we ran in to each other coming in to the building after a long night out drinking on my end and what by the looks of things was an equally boozy night for her. We made out a little on the elevator. A few weeks later, same thing, except she came to my apartment to continue to make out and let my hands wander underneath her garments. They liked what they felt. So I naturally would like to have sexual relations with her. However, yesterday I saw her leaving the apartment with a man who looked to be in his mid-late 40s, and two younger kids, I would guess 4 & 6. Being a divorcee who was cheated on I have no desire to put this man through that. However, I have talked my way in to thinking that maybe she is his daughter or some kind of relative. How do I go about finding this out? I would ask her, but yo no habla espanol, and asking this man if the sexy young thing he lives with is his kid or wife seems a bit awkward.

Oh, for God’s sake. Learn some fucking Spanish. If hot Puerto Rican ‘tang can’t get you motivated to do something about the language gap, then you’ve gotta be one of the laziest people on the planet.

Football: As a Bengals fan, I am curious, do you see last years semi-success as a flash in the pan thing or do you think we can be competitive again in the coming years?
– John John

As a Bengals fan, you should already know the answer to that.

Fellow Douchers,
Football: No question, just want to say how thrilled I am that Rex Ryan is the HC of my NY Jets. HOW THE FUCK YOU DOIN’, BOYS?

Ugh. I’m so jealous of Jets fans. I wish I could be one-tenth that excited about Pete Carroll. *drinks bleach*

No Pants Dance: I really dig this girl at work and we talk/email all day. She texts me a lot too while not at work, but nothing more than random stuff. Naturally, she has a BF. The main problem is that she moved from a couple states away to live with him so obviously it’s serious. Even if they break up I imagine she would just move back home (recent college grad). Should I just give up hope and be glad I have a cool friend at work, or keep plugging away and perhaps eventually tell her how I feel?

No way, keep being her friend. Every time I’ve been in love with a girl — like, stupid in love — after the break-up she’s started dating her closest male friend. Those three girlfriends have now been dating that rebound friend for one, three, and six years, respectively. Do I hate those guys? Why yes, yes I do. I’m pretty sure I always will.


Sex (kind of): I asked out a girl I know from church a few months ago, and she turned me down. Recently, she told me that no one had ever asked her out before, so she freaked out and turned me down. Basically, she asked me to ask her out again so she could say yes. So I did.

Ooh, a retro question! It’s like watching a black-and-white movie from the ’30s!

I’ve never really been in a relationship that lasted longer than a month, nor one that didn’t end with one of us saying “This isn’t going anywhere. Let’s try to go back to being friends.” Before this girl, I had only been kissed once (at 20) when the girl I was seeing was drunk and feeling guilty about using me to get to my roommate. (She confessed this less than an hour later.)

So after our second date, I give her a hug, and tell her “You have to look up so I can kiss you goodbye.” She looks up and smiles, and I move in for a kiss.

The kiss lasts a second or two, and I feel like I fucked the kiss up COMPLETELY. I feel like this is something I should know how to do. Given that she’s inexperienced too (so I can’t ask her to teach me,) how can I get better at kissing?

Um. *scratches head*

I’ve been answering questions about how to get a girl to do anal for so long, I don’t really know what to do with this one. And I’d feel really weird giving another man kissing tips. All I can say for certain is that whatever you’ve seen in porn, DON’T DO THAT. But if you need to turn to movies, I’d recommend being like George Clooney:

Fantasy: A buddy of mine from high school wants to run a fantasy football league in our circle of friends. Three people have committed, and realistically, one of them is incredibly flaky and will probably not make it 17 weeks. In your opinion, what’s the minimum number of teams required for a successful league?
Inexperienced at two things I’ve heard are great

Twelve is ideal, 14 is slightly too many, ten is slightly too few. Eight is the smallest acceptable league, and even then every team will be stacked to the gills.

The next question is a tough one from Drew’s Deadspin submissions:

Next month I am going to a wedding of a mutual friend of both mine and my current girlfriends. I know there is going to be a girl there that I got drunk and cheated on my girlfriend with. She is borderline crazy (which is part of the reason we hooked up in the first place, she is one of those girls you can tell from looking at her is crazy in the bed). Anyways I have a feeling she will get drunk and either:

A. Become flirtatious with me (and anyone else with a pulse and a dick)
B. Bring up our past discretions in a loud annoying drunk girl moment and people might hear.

And this is why you only cheat with hookers.

My worry is my current girlfriend may find out.

Ya think?

So should I do a pre-emptive strike and tell my girlfriend this chick was psychotically obsessed with me (which is borderline believable at best, I do drive a Dodge Stratus) and then I have the upper hand should something happen or should I roll the dice and play it cool and if something does happen deny, deny, deny?

Oof. Having been the victim of a crazy stalker attack at a wedding — albeit one I didn’t cheat with — I can confirm that this can really ruin a night. Is it possible for you to play it off like you didn’t realize she’d be there? Like, can you be sitting in the church, and then be all, “Oh shit, that crazy bitch is here!” Then there’s some immediacy to the two of you avoiding her all night.

If not, do a preemptive strike. It’s the closest thing to honesty, which I suppose is the next best thing to actual honesty in this case.

Dear Japs,

Note: This is from someone with an Asian last name.

Football first of course: I am most likely keeping Fitty and Turner, but could potentially slot G.Jennings or Slaton in there… are either of those better long term options, or should I just try and grab them in the draft?

Keep Fitty and Turner.

Sex: Is there ever a situation where nailing a good friend’s GF is acceptable?

Nope. Well, unless he just died, and she needs to be comforted. With your dick.

On a related note, one of my good friend’s GF has been coming on to me on and off the past few months. We almost got together before they did, but I kind of had a GF of my own at the time, a minor issue. We are fairly close now, she tells me about her sexual frustrations, we flirt, and I think something happened one night where I got blacked out. On the other hand, I know they love each other,

Oh yes, it’s very easy to tell from her flirting with you and admissions of sexual frustrations.

and I completely respect him,

Fuck you, no you don’t.

so nothing will probably happen. I think I just need someone else besides my conscience to tell me to pump the brakes before it gets out of hand.
Thanks all,
Probably A Bad Person

You want to actually be a good friend? Don’t be close to your friend’s girlfriend. Just fucking DON’T. She sounds like a scheming tease, but you’re the one who’s REALLY in the wrong here.

Level with her and tell her that the flirting is inappropriate, and that you’re not going to be her confidante any more. And if she does it again, tell your friend about her inappropriate behavior. Sell that bitch out.

Hey boners,
So I got dumped by my ex about a year ago- we’d dated for over a year, and everything seemed to be going swimmingly, but then she witnessed a girl drowning firsthand (she lifeguards during the summers). Needless to say, it fucked her up emotionally for a while, to the point where she had to go to therapy. I was happy to support her and help her out, but I guess she felt she needed professional help, so she went. The therapist (fucking quack) told her that she needed to focus on herself and being a college student (I was older and thus graduated before her.) So, she dumped me.

You got dumped because your girlfriend’s a crappy lifeguard. That sucks.

It took me a while to get over it; in fact, I’m still not completely over her. For a while, we didn’t talk at all- I didn’t want to be in her business, and she was busy with her own stuff, I guess. Recently, though, I was on a date and she texted me (I have a feeling she knew I was on the date, since the girl I was with had written on my wall on Facebook about coming to visit), and since then we’ve spoken a few times. I’m going back to school this weekend for an alumni event and I’ll probably run into her- problem is, I want to tell her that I still really care about her, but then I risk not hearing what I want and potentially ruining my weekend. Is this advisable, or should I just enjoy myself and ignore the impulse?

Go ahead and tell her. Telling an ex that you really care about them and still have feelings for them isn’t that huge of deal; it kinda happens all the time. And since you’re sharing positive emotions, it will probably be received warmly, even if she doesn’t feel the same way. Either way, getting your feelings off your chest will feel better in the long run.

Football: I might be in a FFB league with my mom next year. Probably what I deserve for being a Patriots fan.
Help would be appreciated,
H. Alvardro

Hahahahaha, that’s awesome. IS YO-WAH MUTHAH GONNA BREASTFEED YA THROUGH THA DRAFT? I have never before heard of such ripe ground for shit-talking. Good luck with that.

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