KSK Mailbag: Looks Like We’ll Be Going Down Together

02.27.14 4 years ago 53 Comments


Oh, hello. Welcome to the mailbag. My apologies for not posting sooner — one of the letters this week features someone with an attractive co-worker he can’t date, which sent me down the internet spiral of reminiscing about “The Last Temptation of Homer,” one of the finest Simpsons episodes ever made. You can relive my reliving on Tumblr, if you’d like.

As always, thanks to everyone who wrote in. If your letter isn’t featured this week, don’t worry: it’s filed away for future editions. Want to write in? Hit us up here.

Let’s dive in.

Dear KSK,
Football: for the football fan, is there a worse month than March? Free agent signings are a giant cock tease.

Let’s not kid ourselves: anything that isn’t the season is all pretty terrible. Like, are we really getting down on March for not having the combine? The draft? Training camp? It’s not like those non-events are particularly bright spots on the calendar.

Personally, I’m okay with March: it’s so far removed from football that I don’t expect anything of it. Throw in “Archer,” “Justified,” and March Madness, and I’m generally sated in terms of entertainment. The REAL dark part of the calendar, for me, is after the NBA and Stanley Cup Finals end in June, right around the same time that the new season of “Game of Thrones” ends. July hits and all you’ve got is baseball (ugh) and boring news from your favorite team’s beat reporters about an undrafted free agent moving up the depth chart. That’s agony.

Sex: I’m single but no longer pursuing relationships. Without getting too much into it, I basically don’t think I’m good enough for a relationship with any person I’d want to date (ie unsuccessful, not a particularly attractive person who doesn’t know what they want to do in life at an age many of my peers have). Despite that, I actually am happy with no one and suspect that I’ll be happier if I never try.

So … do you have a question, Detective Cohle? Or am I just supposed to crack open this sixer at noon on Thursday and expound on the meaninglessness of human existence?


If you’re happy with yourself and where you’re at, great! You don’t need to be out chasing women just because society or your hormones think you should. But I don’t think that’s really the case here. I get the feeling that you’re not getting into relationships because you’re not happy with yourself. And that’s okay too, as long as you recognize that and take steps to become happier with where you’re at and where you’re going.

Not everybody has their life figured out at 22 or 26 or even 38. I was more than two years out of college before I realized I wanted to be a writer, and it would be another four years until I got paid a living wage to do so. In between, I worked some shitty jobs and ultimately went seven years without health insurance. This isn’t a path I’d recommend for anyone else, but I’m happy that I took the time to figure out a career that I enjoy, instead of, say, managing logistics for FreshDirect or whatever.

So define “success” by your own metric of life satisfaction, not by what other people are doing. If part of that metric is not being in a relationship, then good for you. Enjoy the extra money for beer. If not, maybe figure out your own life before writing off any emotional investment in the opposite sex for the rest of your life.


Mr. Bout-Dat-Action Boss,
Fantasy – Our 12 man, mostly standard snake-draft league has previously been under three-keeper rules, but this offseason will be moving toward a semi-Dynasty format. For the foreseeable future each owner will be keeping half of his roster (8 players), with no penalty for rounds kept. Our line of reasoning: we did not want to eliminate the draft entirely and in theory, this will still leave rookies, cast-aside veterans, and low-upside starters available for each year’s fantasy draft. Two questions:

1. Considering we are past the point of no return, how badly did we just screw up our league? The draft is near the top of everyone’s list each year of enjoyable things about fantasy football, especially since this league is a bunch of college friends that only get all 12 of us together once a year. Can we still keep this thing a huge event like it has been for us in the past?

Larger keeper leagues definitely take some of the excitement out of the draft — it’s inevitably less exciting when everybody has, say, four positions filled and you draft Jeremy Maclin in the first round. Your semi-dynasty league will likely see an exacerbated version of this phenomenon.

However, I think you can still have a highly engaged draft, thanks largely to your auction format, which requires more attention and investment. As long as everyone adjusts their expectations and attends for the camaraderie more than the fantasy implications, I’m sure you’ll be fine.

2. What would your strategy be in this (auction format) draft? This draft is obviously of greater importance because it will be the last draft where all the players are available. If someone drafts LeSean McCoy and chooses to keep him every year, Shady could retire on that owner’s roster. In addition, top rookies like Johnny Manziel will likely be coveted and thus overly expensive. Where do I find the value without missing the studs I want to go get?

I’d let everybody else overbid on rookies while I focused on young players who are already proven: Eddie Lacy, Keenan Allen, Andrew Luck, etc. They’ll still be relatively expensive, of course, but I’d rather have Russell Wilson with a decade to grow as a player than Peyton or Brady at the end of their careers.

Relationships – I am a single, 25 year old male making a decent starting salary in a major U.S. city near the university I attended. I am enjoying everything that situation entails to the fullest, dating a little but mostly being non-committal towards women. The issue: two women I really like and that I have been seeing lately know each other and one (possibly both) have some idea that I’m also hanging out with the other. I have a definite preference for girl A but I’ve known girl B longer and have been more involved with her. The ideal situation would be for me to keep dating both of them casually,

Haha, no shit. “I mean, in a perfect world, any woman I’m attracted to is available for sex at any time…”

while the more realistic scenario involves a crash-and-burn. Maybe we run into one while I’m with the other, maybe they exchange texts and figure it out, but this never ends well. The main thing in my mind is that I’m always honest about wanting to stay single and avoid being in a committed relationship, which they seem okay with. Do I need to pick girl A, or can I keep the dream alive for a little longer?
Maybe I’m Just An Asshole

If you suspect that your present arrangement is close to crashing down around you, let me assure you: it is EVEN MORE TENUOUS THAN THAT. I live in one of the largest cities in the entire world, and it is still not large enough to avoid running into exes or prevent jilted lovers from meeting by chance and comparing notes. If you keep seeing both of your women, it’s only a matter of time until the universe conspires to put you in the middle seat between them on a cross-country flight. And guess what? Your seat won’t even recline, because fuck you.

So yeah, date one girl at a time. Even if it’s just casual. I promise you this is the right decision.


Hey captain of courtships and ca…football,
Football: Any thoughts on Foles? His output seems unsustainable, but it was a surprisingly long stretch of good play with subpar receivers (Riley Cooper had some incredible luck with bounces). I’m thinking about him as a mid round QB, but I just can’t convince myself on him for some reason.

I dunno. I think that fantasy owners discount players in Chip Kelly’s offense at their own risk. Like, I don’t trust Foles as a fantasy quarterback if he leaves for Cleveland or Minnesota in free agency. But running Chip Kelly’s offense? He’s going to get yards and throw touchdowns. And while the NFC East won’t have QUITE the dogshit lineup of defenses every year — Foles’s TD-INT ratio of 2013 is particularly unsustainable — I think he’ll remain an excellent mid-round option.

Dating: I’ve only had 2 long term relationships, and both ended pretty acrimoniously. Since then, I’ve followed the captain caveman post breakup plan to a T. I’m healthier than I’ve been in a long time, and in some self discovery, came to the realization that I’m an alcoholic. I’ve spent some time learning how to live a sober and fulfilling lifestyle, and decided to start dating again. It hasn’t been a rousing success.

After a few dates, I told one woman that I don’t drink because I had some trouble with it in the past and I’m a lot happier and healthier this way. The date went ok, then after, she texted me and said to never contact her again.

Well, I guess that’s better than not hearing back?

Went on another date and took her to dinner and a movie. She asked why I wasn’t having a drink with dinner so I told her honestly, I don’t drink anymore. She said that was freakish and didn’t want to see me again.

Had that happen 2 other times and it’s shitty as hell. I’m a little chubby, but otherwise healthy, ok looking, sociable, have a steady, solid job and turn 30 in a month. I generally have my shit together, so this is a frustrating response. Any advice?
-True Defective

You have to understand that teetotalers are intimidating to drinkers. Most people — or at least your average twentysomething — relies on a couple of drinks as social lubrication on an early date. It boosts confidence and lowers inhibitions, which makes breaking the ice with a stranger a lot easier. It’s such a standard practice that it’s uncomfortable when the other person says “no thanks” to a beer. That tips the drinker’s social world on its head. Suddenly they become hyper-aware of their own drinking, and worried about whether the non-drinker is judging them. Your temperance makes them self-conscious, which isn’t exactly paving the way toward romance.

I’m married to a non-drinker, and it pains me to admit that I probably wouldn’t have pursued her if I’d met her a few years earlier, when I was more self-involved and less likely to understand such a minor foible. But she let me know up front that she didn’t mind me drinking, and I gave her the benefit of the doubt because she was pretty and made me laugh a lot. And now I have a designated driver for life. Sweet!

So, given my experience, my advice to you is (a) let people know up front that there’s no judgment that comes with your personal decision, (b) date women who are more mature, and (c) be patient. Dating sucks for everyone, and your personal horror stories, while definitively your own, aren’t any worse than anyone else’s.

p.s. As noted with other disclosure-related dating problems, this can be circumvented with an online dating profile, where you can screen the shallow girls who think not succumbing to alcoholism is “freakish.”


Hi Matt,
I’m a huge fan of your post-breakup plan and normally treat it as gospel, but unfortunately I’m in a tricky situation where I’m unable to get past the most important step: Act as if they’re dead.

Well, that’s an indelicate summation. Technically, the step is to “mourn the loss of your relationship,” but yes: I do recommend that you should move on as if your ex has passed away. (It prevents drunk texting.)

Long story short, I began casually hooking up with a girl about a year ago who I’d met at various industry parties, and not only did she end up leaving her job to come work for the same company as me (not something that caused any concern, considering the casual nature of our relationship and the size of the company), but after a few months she was transferred to a new group and now reports directly to me.

Ruh roh.

We stopped seeing each other a few weeks before she found out she was being transferred, so it wasn’t a situation where I had to worry about sneaking around with an employee of mine, but we now spend a ton of time together and my feelings have popped up again, stronger than ever.

Double ruh roh.

I’ve read enough of your mailbags to know that it’s a horrible mistake to date someone you work with, so I’m trying to go in the complete opposite direction and get over her as soon as possible. The question is: How do I successfully do this when it’s physically impossible to cease all contact with her? I love my job, so leaving or transferring isn’t an option I’d like to seriously consider. How am i supposed to get over someone if i can’t finish the first step of the plan?
So Screwed


Do you have any idea about how your co-worker — let’s go ahead and call her Mindy — feels about you? I mean, if you only ever saw each other casually, it’s entirely possible that she’s moved on and/or doesn’t see you as a viable emotional commitment. Because if doesn’t even want to date you, then you can just reside miserably in the Purgatory of Unrequited Love.

BUT, assuming Mindy feels the same way that you do, then you’re both looking at long work weeks of aching for each other with fiery loins until some business trip or late night at work ends up in steamy, illicit business sex. You know, the kind where neither of you actually get all your clothes off before going at it like animals because it’s all you’ve been thinking about every day for months? And if THAT happens, then you’re looking at (1) going to H.R. to get reassigned so you can pursue a relationship, (2) pissed off subordinates who think you’re giving preferential treatment to the woman you’re sexing, or (3) the turbulent waters of sexual harassment allegations.

Look, you dated this girl casually for several months without taking a serious move to seeing each other exclusively. That suggests to me that you were never THAT into her, and the only reason you are now is because she’s a forbidden fruit that you’d like to pluck again. So distract yourself with other women. Get on Tinder and start swiping.


Oh Captain my Captain,
Actual FF Question in February: Keeper league. I get to keep one player I drafted in the round I drafted him. Scoring: .5 pts per reception, 6 pts per rec TD, 1 pt per 10 yards rushing/receiving, none of that punt/kick return crap. I took Jordy Nelson in the 7th round and Percy Harvin in the last (15th) round, thinking I was shrewd. Should I even be considering Percy or am I totally overthinking this? Jordy seems like the obvious choice, but I hate having to root for a Packer and I drafted Percy (and kept him on my roster all season) specifically with an eye toward my keeper decision. Talk some sense into me.

Well, you’re asking a Seahawks fan, so I’m naturally a stupid homer who thinks Harvin’s injury woes this year are going to be oveblown in 2014 projections. So with that caveat aside, I think Harvin is too exceptional a talent to not keep for a 15th rounder. He had 11.5 fantasy points in the Super Bowl — on four touches. Sure, Nelson will probably put up bigger numbers over the course of the year, but Harvin’s the more enticing value.

(I’m a homer. Keep Nelson.) PERCYYYYYYYY!!!!! (Don’t listen to me.)

Relationship: I just went through a brutal break up where I was cheated on in a pretty devastating way. I have successfully completed stage 1 of the CC PBP, and find myself somewhere in steps 2 and 3. Steps 1 and 2 have been made slightly easier on me by the fact that there wasn’t great overlap with her friends and my friends. As a result, my friends/family got my back and cut off ties with her while her friends/family are no longer a part of my life. However, when you date as long as we did (the better part of a decade), there is bound to be some overlap in “our” friends.

I have a buddy who I knew before our relationship began who is currently dating one of my ex’s friends. I haven’t seen him since the break-up or talked to him about the break-up. I know he knows that we broke up, but I do not know exactly what he knows (i.e. he may just think that we are no longer together and split on amicable terms — any information he has came from my ex). I also know that he has hung out in a group with my ex since the break-up, which is understandable because of his girlfriend situation. I am telling you this because the details behind the break-up/cheating/betrayal are bad. So bad, that part of me feels like anybody who knows what she did to me and can still be friendly with her is not really stepping up for me.

I have gone back and forth on how to handle the situation. Am I being unreasonable about how much my friends should care about the situation? Do you have any recommendations on how to deal with this particular buddy, specifically? If I tell him all of the details, I’m afraid that I am indirectly asking him to pick sides unfairly. If I tell him all of the details, do I also tell him how I feel about him continuing a friendship with my ex? If I don’t address it, he might feel guilty later if/when he finds out details for acting friendly with my ex, who is truly a horrible person. If I act like nothing happened and never address that this is bothering me, this may just fester and kill our friendship because I may continue to resent him hanging out with my ex.
Clever Pun

Two things here.

1. Spread the facts of your break-up far and wide. You don’t even have to bad-mouth her; let her deeds speak for themselves. Your ex isn’t entitled to fuck you over AND keep her reputation pristine. Fuck her. Scorch the earth.

2. Don’t expect your friends to tell her off or shun her just because she treated YOU like shit. For example, your buddy is dating your ex’s friend. Do you think HE calls the shots about who they hang out with? Hell no! He hangs out with whomever his girlfriend wants to hang out with, and he’s probably going to be cordial to your ex because (a) it’s easier and (b) at the end of the night, he’d rather have sex than an argument with his girlfriend. It doesn’t mean that he approves of what your ex did to you — he’s just navigating life, trying to drive around potholes and speed bumps.

You are, of course, justified in writing off this friend if he makes that decision, but I don’t see why that’s necessary. He’s not the one who cheated on you.

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