Dating Unemployed People Sucks: The KSK Sex/Fantasy Football Mailbag

06.02.11 6 years ago 66 Comments

Aw, crap. Mailbag’s late again this week. Sorry about that. Let’s get right to it:

Good afternoon (I’m guessing you’re doing this in the afternoon),

Actually, I review the mailbag questions and format them on Wednesday night. The responses get crafted throughout the day on Thursday, which is why the mailbag sometimes runs late. The mailbag also runs late when nude photos of Blake Lively show up online and I spend the morning saving the high-res images to my hard drive and staring in blissful wonder at the fulfillment of so many wishes.

Some Fantasy/Sex Mailbag questions for you. Sex first: A few weeks ago, I was out at a bar and started talking to a girl. Things went well and we exchanged numbers and texted each other the next day. Because I’m a dumbass, I didn’t really follow up with her and try to secure a date of some sort. We’re still friends on Facebook and she’ll occasionally ‘like’ a picture or status update I have, so I’m guessing there’s some interest from her. But I’m unsure of how to re-establish contact. I know calling her is the best way, but I’m unsure of what to say. I’d like to avoid “It’s [NAME], from [BAR] a few weeks ago. Um, call me!”

Do you have any pointers or advice on what my first few sentences should be?

There are going to be differing opinions on this one. Some of the older-school folks will claim that a phone call is most appropriate, because it takes more balls and is the most direct form of communication. But what happens if she presses “ignore” on your call? You go to voicemail and stammer out something that’s either too long and apologetic or too abrupt and uncaring, and then she doesn’t listen to it for two days because, honestly, voicemail is a fucking pain in the ass that everyone with text messaging has grown to hate.

I think a simple text message along the lines of “Hey, sorry I messed up and never asked you out. Can I buy you a drink/take you to the movies this week?” is all you need. If she responds with a yes, you text, “Excellent, I’ll call you tonight.” If she ignores you, oh well. Lesson learned.

Another option that I like is the Facebook message, but that’s because I like to communicate in more detail when I’m wooing a woman. If writing is one of your strengths, that may be a better option.

Fantasy Football: I’m in a keeper league and we can keep four guys. Your four keepers are effectively your first four picks. My team made the playoffs so I’ve got some options. Phillip Rivers and Michael Turner are the ‘duh’ keepers. But I’ve also got Jahvid Best, Marques Colston, Hakeem Nicks, Kenny Britt, Marshawn Lynch and Shonn Greene as options.

My gut says to keep Rivers, Turner, Nicks and Best. Thoughts?
The A-Train

I’d probably lean toward Colston over Best, but Jahvid is the bolder choice.

I really like all of your players, though. They’re not keepers, but I think Greene and Lynch could be sleepers next year: Greene is massively talented but devalued after a disappointing 2010 season, and Beast Mode is still young and playing for a Seahawks line that was young, injured, and playing in a new scheme last year.


This next letter made the mailbag for its pure swagger: part life coach, part asshole, all confidence.

Cut the music,
Sex/bragging: I’ve anxiously awaited the mailbag every week, it’s hysterically funny and actually pretty great advice. But the whining has got to stop from some of you. It’s getting worse each week and I’ve noticed a trend where it gets real bitchy in the offseason which is ridiculous because it’s Spring/Summer and if you’re not busy pulling wool out of your teeth, then what the fuck are you doing? Life definitely sucks at times no doubt. I was on the verge of marriage with a looney bird (albeit a looney bird with amazing boobs, low self esteem and issues with dad, aka jackpot!) who called it quits with seconds to spare. Of COURSE she was fucking my friends, SURE she was fucking my coworkers, YOU BET she was fucking her coworkers, that’s normal crap to find out after a break up. But, don’t mope around when shit like this happens! Share sex stories and send naked pics to friends, family or random people and have fun with it.

Sure shit can seem real rough but it shouldn’t take long to realize how easy it can be to either go out and find some strange to take to pound town OR to find a non slutty girl to date, which is definitely the harder of the two. If you actually pay any attention the advice is always the same whether it comes from your buddies or the Don Juans at KSK: sit up straight, lose some weight, don’t be an asshole, don’t be a douche bag (they’re different), have at least one interesting thing to talk about, find your balls and then shave them because it’s just common fucking courtesy (get it? like literally ‘fucking’ courtesy, like sex, get it? fuck you, i don’t have to impress you). It really doesn’t take much to make this shit happen.

Also, stop asking about how you can stick your penis in some poor girls fart box! If you ask me it always ends shitty (pause for laughter) and don’t be a puss, if they like you enough for you to put them through that pain then be a man and let them stick a finger up your poop hole. I promise, you’ll never ask for anal again.

I don’t think I’ve answered an email about anal in at least a year. Those questions were browbeaten out of the mailbag ages ago.

By the way, screw your long-distance relationship moratorium, being in one is the best thing that’s happened in awhile.

Better than Osama bin Laden getting killed?

I’m going on 6 months in an LDR and it’s awesome.

“Hey everybody, go to hell with the repetitive subject matter! Now listen to me bring up the most worn-out mailbag subject of the last six months.”

Every week or two I get on a plane, have a ton of awesome sex, have someone tell me how handsome and fun I am and then fly home where I don’t have to deal with anyone’s day to day bullshit and they don’t have to deal with mine. Maybe it’ll work out, maybe it won’t but right now all I’m worried about is that this girl is the nicest and coolest person I have ever met and without a doubt it’s the best sex I could ask for. She lets me do things to her that would make her father cry but at the same time she’s so cool that I couldn’t wait for my mommy to meet her and really what more do you want?

Well, bully for you. Scroll down to the comments to read what I’m sure will be nothing but praise and compliments about how awesome you are.

Football in the groin: There better be a GD season this year, I’m primed for making fun of Brady (because of how jealous I am), listening to Joe Buck (seriously can it get any better than this guy?) and critiquing everything my favorite team does (because, how the hell could they not have gone for two?! those freakin’ idiots). If there is a season, shortened or not do you have any advice for either trying starting a league or an approach to take for weaseling into an existing one? I just moved and I don’t like playing with people that I can’t harass in person but I don’t know how I should bring it up to people I barely know or gauge how seriously they would take it because FF is serious business.
Smash dem’ guts,
R. Goodells Weird Neck

Step 1: Lay off the Red Bull, Macho Man. You’re scaring away what few women read the blog.

If you want to be in a fantasy league with people in your area, spend your summer making friends. Go to the local sports bar tonight; if there are guys in tank tops yelling at the TV and cheering for LeBron in the NBA Finals, chat them up. I bet y’all will get along just fine.


Dear KSK,
Sex: I really love my girlfriend. We’ve been together 3.5 years and now live together (after 2.5 years of long distance). She’s in med school and I’m graduated but have been unable to find a teaching job. I work a shitty job that pays me very very little and I can’t stand it anymore. This has caused no small amount of doubt (from me) about our relationship because my hatred of my job has sort of spilled over into hating everything about my life, including my girlfriend.

Seems healthy.

I moved to her city to be with her and hopefully start my career and then things would just progress naturally from there. But things haven’t happened that way and I find myself waking up everyday thinking about how I should quit my job and break up with my girlfriend and go somewhere, anywhere else and start over. I, for a while, felt like this feeling was solely generated by the hatred of my job/life but now I’m not so sure. I also feel like, after 3.5 years, she should have some sort of say and understanding about this decision. We’re both adults and we both should be able to sit down and talk about how our goals for the next five years (her: get married, have kids, become successful doctor. me: find a job) are totally different and how we have two different views on what everyday life should be like (her: I’m the stay at home dad. Me: I’m NOT the stay at home dad, in fact I’m not a dad at all).

Jesus, dude. She wants kids and you don’t. And you’ve been together 3.5 years.


NOTE TO KSK READERS — This dude is too late to help, but here’s a handy guideline: it is best to discuss whether you and a potential partner share the same goals for having a family sometime BEFORE you embark on a long-distance relationship for two and a half year, then move to a different city to live with that person, then live with that person for a year. And remember, this helpful advice comes totally free of charge. What a deal!

I honestly just don’t know if I have the stones to have that conversation because she’ll cry and I’m not very good with sticking to my guns when a woman is crying. But, if I know I’m going to say, at some point, “I think we should separate/break up” shouldn’t I just open with that? (We’ve already had one conversation involving how unhappy I am here and how I was going to look for jobs (including ones outside of teaching) in other cities and how that might make me unable to move/live with her for multiple years and that might cause us to break up. So this isn’t coming out of the blue.) I really do love this woman and want nothing but the best for her. I just feel like I am so unhappy that whatever I bring to the table isn’t good for either of us anymore.
-Sad Wagon

That’s tough, man. Being unemployed or employed at a shitty job for any extended period of time can be absolutely crushing. I feel you: I went through some lean times when I moved to New York City, burning through my savings and feeding on Ramen noodles and slices of pizza before landing jobs that sapped my spirit and barely paid the bills — and I didn’t even have a loving, caring girlfriend to help pay the rent and direct my unhappiness at.

Whoops, sorry. I was trying be sympathetic, you miserable son of a bitch. Given the tone of your email, your girlfriend has to be a goddam saint to put up with the dark cloud you must cast over the apartment.

We’re all responsible for our own happiness. Love, work, home: all that shit is ultimately controlled by you. You sound like someone who needs a change in at least one of those three categories. If you and your girlfriend can’t have a mature conversation about the future because you can’t handle the sight of a woman crying, you’re only sentencing yourself to a whole fucking ocean of tears down the road.


Dear KSK,
Some eight years ago, give or take, a student at my school built a service into the school website called “Hookup.” People can log in using their school usernames, and can enter another student’s username into a list. Those students receive an e-mail telling them that someone has entered their name, but they can only see who it is if they enter the same person’s name on their own list, at which point both people get notifications that they have a match, and then awkwardness ensues. Like I said, the site was built years ago, and while apparently it was popular for a little while, its fell off the map pretty quickly, for fairly obvious reasons.

Flash forward to this winter: That same former-student is back at school as a guest lecturer (he turned out to be a pretty successful dude) and some idiot on the school paper (me) decides to write up a feature about his work, mostly because we needed to get some filler copy. One of the things that comes up in the article is “Hookup.” The site’s usage explodes immediately after the article comes out – keep in mind no one knew about this for years – and just as rapidly dissipates once people get bored guessing who added them, or realize it was just their roommates messing with them.

If I may:

Another rapid transition: Back in the fall, I met a girl at a party who I hit it off with surprisingly well – this is not something that happens to me all that regularly keep in mind. We didn’t hook up, mostly because her friends decided to be buzzkills, but shit happens. We flirt briefly on Facebook after that, but after a few days of radio silence the connection seems dead, and since we crossed paths maybe once for the rest of the semester, nothing came of that.

Coming back in the spring though, suddenly our schedules are a little more compatible, and we run into each other a decent amount. It’s all very flirty, and shit is going nicely. I keep hoping to run into her at a party, but no luck, so eventually I invite her to a party at my apartment. She doesn’t show up, and I’m sufficiently disappointed, etc. This is the same week that the article about “Hookup” comes out though, and I wake up the next morning to an e-mail saying someone added me. In my hopeful (and I think still slightly drunk) state, I add her name and, what do you know, it’s a match.

I don’t have her number at this point, so I have to find an opportunity to talk to her in person.

Or you could have contacted her on Facebook, smart guy.

It takes a few weeks (this happened just before spring break) but eventually I find the opportunity and the balls to ask her out, and she says yes. Victory for me, it seems, but when I try to actually have a date of any sort, she either is busy, or ignores my messages completely. I try a few different times, doing my best to avoid being annoyingly persistent, and eventually the semester ends with no success, and no real indication from her that she has any intention of ever going out with me.

My question is this: What the hell happened?

She wasn’t interested and/or you blew it.

Was she messing with me from the beginning?

I doubt it. She might have liked flirting with you when she was drinking, but then wasn’t interested in you when she was sober.

Did I do something wrong and scare her off?

It’s possible. You’re a young journalist, which means you’re probably an awkward weirdo with no game.

Do I owe the guy who built “Hookup” a high five for creating a good lead, or a deadarm for creating such a confusion (keeping in mind he was my professor this semester)?
Not Getting Laid Via Journalism

It wasn’t a good lead at all. The good lead was you hitting it off at the party last fall. The “Hookup” part of this story is just a big red herring and waste of column space.

Forget the girl; it’s not worth the brainpower trying to figure out what went wrong. Just be more confident. Try to find a happy medium between your email and the rant above from the Coke Bandit, whatshisface, Goodell’s Neck or whatever.


Dear Stone-age Swami:
FF first: I am the commissioner of a 16 team league comprised of mostly guys from college with a few random friends thrown in. About half the league lives in the same city and the other half is spread out throughout the country. Now that we are entering our second year, I need some advice on how to approach setting the league when its almost impossible to get a consensus amongst all the players. I don’t want to be a tyrant but it seems like the easiest thing to do is just set the rules myself to prevent an endless debate on the details. Some things that need to be decided are: Draft order (Random, inverse order of last years standings), Where to have the Draft (we did all online last year and I thought it sucked but it would be nearly impossible to get everyone in the same place), Keepers (yes/no, if so what round), Fees, Trophy ( I was thinking title belt at the start of last year but I almost don’t want to do it now b/c everyone will think I am copying Aaron Rodgers). Any advice would be greatly appreciated.

In order:

  • Draft order: Random, decided ten minutes before the draft.
  • Draft location: Online if you’re spread over the country; in person if you can get 75% of the owners in the same place.
  • Keepers: Your job as commish is easier without them.
  • Fees: Yes, variable depending on people’s employment. $20-$50 is normal for us middle class folk, though people with better jobs and gambling addictions may scoff at those numbers.
  • Trophy: No. You’re adults. Money is your trophy.

Sex: My GF and I have dated for almost a year and a half, and we have lived an hour and a half apart the entire time (not really long distance but annoying non the less). She just lost her job and is talking about looking for work in my city. I am very excited about being in the same town and getting to see her more often. But, in order to move here she is going to have to live with me, at least temporarily, and I have never lived with a girlfriend before.

I love her but we have never been able to spend more than a week together because of our work commitments and I am a little scared about what would happen if it went south and she didn’t have any other place to go (right now her only friends in my city are my friends). I truly think this is the girl I am going to marry, but I am not the type of person to jump blindly into any situation. Am I wrong to suggest that she should try and find her on place as soon as possible, or should just man the F up and let it ride and deal with the fallout if it ever goes south.

I sincerely hope I don’t come across as a whiny lil bitch.
-Clever Pseudonym

I don’t think you’re a whiny bitch; your concerns are perfectly valid. The situation you’re in is like having a romantic picnic on a beautiful spring day in a flowery meadow that is littered with anti-personnel mines: it’s possible that you’ll have a wonderful time, but you’re right to be worried about losing your legs or ending up a bloody mist.

Obviously, having your girlfriend in the same city as you would be a great step forward for your relationship, but having her in the same apartment may put undue stress on you two, especially if her unemployment streak stretches longer than anticipated.

The best thing you can do is be open and honest about your feelings right now: tell her that you love her and you’re excited to have her closer to you, but express that her living with you might be too big of a leap and could actually hurt your relationship. Explore other options, like helping her find her own place, or seeing if her parents will help financially, or allowing her to crash at your place during the week while she interviews for jobs. IMPORTANT: you need to get her to see eye-to-eye with you on this, because if you let her move ANY of her big stuff in — table, books, armoire — be prepared for the possibility of her staying with you a LOT longer than planned.

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