KSK Mailbag: Just F–king Go For It

05.01.14 3 years ago 51 Comments


I meant to recommend this the other week, but neglected to do so because I was whining about dental work: The Toast’s Lessons I’ve Learned From Being a Therapist. It has some similar viewpoints to what we talk about here in the KSK mailbag, but it’s generally more circumspect about life and has the added bonus of coming from an actual therapist, rather than a football blogger. Give it a read — but only AFTER absorbing all of the fantastic life advice below.

I don’t have a fantasy football question. I offer my current clone crush, Tatiana Maslany.


I would just like to state for the record that I’m not watching “Orphan Black” and you can’t make me. I don’t care that it’s good. #BoycottCanada

I have two other questions however:

1. I found out yesterday that one of my oldest friends is engaged to be married next year. His fiancee is great and I am very excited for their wedding.

Conflict: He mentioned that their plan is to get married on Pi Day next year (3/14/15). Six months ago, my cousin, who I held when she was an infant and is practically a sister to me, got engaged and planned to get married that day. I have not been in a scenario like this before, and I cannot imagine missing either wedding. How in the shit-bitching ass-bastard hell am I supposed to choose between the wedding of one of my best friends and the wedding of a close family member?

I dunno, you just do. You go to the wedding that’s more important to you, and if you can’t decide, then you go to the one that’s going to be more fun.

Weddings always shake out this way. When you plan one, there simply isn’t a time or place that works for everyone you want to to be there. Someone will inevitably be nine months pregnant or at another wedding or in Africa with the Peace Corps. It’s just the way things go, and the people getting married will always understand. (Unless they’re assholes, in which case fuck their wedding anyway.)

2. My brother has been dating his girlfriend for six months. Recently they took me out to thank me for taking care of his dog on weekends when they are away, and I spent time with the two of them and her sister. I am single. Her sister is single. Her sister is smart, funny and attractive. I do not often meet smart, funny, attractive women, and I am usually too shy around those I do meet for the first time to do anything about it, but in this case I thought we got along incredibly well from the start. I am also fairly confident that my brother will eventually marry his girlfriend, so her sister and I could be aunt and uncle to their theoretical children. Is it too weird that I am interested in her sister? My initial thought was that it was too strange to pursue anything, but one friend (who has not met her sister) encouraged me (“Just fucking go for it” = flawless logic) and now I’m not sure whether to pursue her or let it go. Does my presumption that we will be family in the future make a difference here?

These are two scenarios I never thought I would have to wrap my brain around, and so far I cannot. Please assist.
-Conway Stern

One of the minor headaches of being in a relationship is that you tend to hang out with other couples, and it can be hard to find another couple where the two women get along as well as the men (or vice versa). So potentially dating the sister of your brother’s girlfriend isn’t weird, it’s SUPER CONVENIENT.

The only hitch would be if/when one of the couples break up: it will be considerably more difficult to get a clean break, but I think the upside is enough to warrant that risk. So I’m on Team Just Fucking Go For It. Actually, that’s pretty good life advice in general — “Just fucking go for it” could probably be a decent answer for 90% of the questions in the mailbag.


Greetings Uff Daddy (bet you’ve never heard that before, right?)
First off, fantasy: Haven’t really got anything for you there because, being Australian, the time difference meant playing fantasy football at an ungodly hour on a Monday morning. NO THANKS. I’m a recent immigrant to the US though so maybe next season? I play fantasy hoops but, despite being the commish of our league, I haven’t won since our inaugural season in 2008. In short: I stink. So in lieu of that, here’s a gif of Christina Hendricks since I’m binge-watching Mad Men.

Welcome to the USA! If your new American friends aren’t referencing the image below, then you need to get new friends.


SEXY STUFF: Since I’ve been binge-reading KSK sexbags, I’ve become very familiar with the Matt Ufford post-break-up plan of late. I’ve adhered to a pretty similar strategy most of my adult life anyway, especially the gym part. I moved to the US last November, and had to end a great relationship because 10,000 miles and an indefinite end date aren’t the cornerstones of a successful LDR.

No. No, they’re not.

So to recap: I’m 28, Australian and in a small town that doesn’t see a lot of either young men or guys with accents. I have a job in decent standing in a fairly poor community, and without getting into specifics I have a little bit of a growing profile in the local media and get recognized now and then. Even individually, these factors tend to attract a solid amount of female attention, which honestly I’m thriving on. I used to do pretty well for myself back home but this is a whole other level. Talk about first-world problems right?

All you really need is your accent. The fame is just gravy.

Anyway my problem is this. I get talking to a girl, we flirt a bit, I get enough signals to roll the dice…and then I don’t know what to do next. Especially sober. My instinct is to ask them out for a drink, but then I freak myself out like “shit, what if we go out a couple of times and she wants to get serious, and I want to continue to flirt and date around, and the girl gets pissed at me?” This has already happened once, thankfully with a girl who lives in the next town over, so it’s not like I have to see her every weekend.

Sorry to ramble. I guess my question is, is there a way to play a small-town field without a) scorching the earth, b) painting myself into a relationship corner or c) trying to avoid any form of drama or crossed paths at all by just taking a vow of chastity until I get a job in a bigger market (hopefully early 2015)?

To make up for the obnoxious word count, here’s a photo of Hayden Panetierre that I’ll most definitely have to scroll past quickly when I’m reading the mailbag at work. 

I Come From A Land Down Under

You’ll pardon me for not bleeding sympathy here, Mr. Handsome Australian Who Wants to Freely Sleep Around With Anyone He Wants To In A Small Town But Worries About His Conquests Wanting A Relationship To The Point That It Inhibits His Ability To Ask Out The Very Girls He Only Wants To Sleep With.

Just be clear about your intentions from the earliest stages. Frame it with your situation: “I’m probably leaving here next year, so I’m not looking for anything serious.” Also: you’re looking to leave this place in less than 12 months; exactly how many scorned ex-lovers are you worried about accruing? Stop worrying  about it and ask out whoever you like. Or, put another way: Just fucking go for it.



My best friend eloped after dating a guy for three months. And now, after a couple years of marriage and an unexpected pregnancy, she’s wanting a divorce. How can I be supportive in her time of need even though I think she’s a dumbass for needlessly creating this situation in the first place?

– A Girl

Just fucking go for it! (Hmmmm, nope. That one doesn’t work this time.)

You  really just have to bite your tongue while you give your friend support, then drink some wine and complain about it to your mom. Or, if your best friend can handle REALTALK, maybe you can say, “Listen, I’m going to give you all the love and support I have, but can I just say one time how fucking stupid it was to elope after dating for three months? Because that was really stupid. Okay, I feel better now. How can I help?” But frankly, I think that helps YOU a lot more than it would help her.

I have a Marine buddy who didn’t respond all that well to coming back from war. Personality-wise, he was fine, but when we got back from the invasion, he immediately married the first girl he dated. They had two kids over the next couple years, then broke up when it turned out she was having sex with another captain in his unit. Anyway, when that happened, I said things like, “Aw shit man, I’m sorry” and not “I always knew you rushed into it!” A divorce is hard enough; stick to love and support.


Hope the offseason is treating you well.

It is, thank you.

My league usually makes a weekend out of our draft with golf/dinner/casino/whatever (it’s mostly local guys), but the only weekend our out of town friend can make it is the last one in July. He’s drafted online a couple times in the past without complaint (including last year), but he has 3 kids, the draft is usually his only visit of the year, and he enjoys catching up with us, as we do with him.

So I thought of doing our draft that July weekend with these rule changes to account for the earliness: 1.) extending our usual 14 round draft to 18 rounds (or maybe do those last 4 rounds by email a few days later), 2.) unlimited first come first serve adds and drops throughout the entire preseason with the maximum roster size staying at 18, and 3.) two required roster cuts down to 16 at some point in August and back down to 14 by the Monday before Week 1, similar to the real NFL. Then, our normal free agent bidding system would start with all those dropped players back in the pool. This way, you have plenty of room on your roster for injury/position battle insurance plus it could bring a fun dynamic to watch your roster during the preseason. Good idea or too much of a hassle?

It sounds pretty cool to me, actually. My only recommendation is skipping Step 1 above — nobody wants a fantasy draft to go four extra rounds, and it will take forever and a day to do four more rounds over email. Just let people expand their roster to 18 with the adds and drops.

As for women, I recently reached out to someone I went out with a few times about a year and a half ago. It fizzled out for mostly dumb reasons on both sides and we lost touch. She replied quickly and agreed about what happened last time, but said that she had just started seeing someone and wanted to find out where it went. I figured that she wasn’t interested and made it up. But since she didn’t make it sound ironclad with the other guy (nor did Facebook tea leaves indicate as such), I thought I’d test it out at some point.

A month later, I asked her out with the caveat that I didn’t know if she was still seeing someone. She said she was, but that it was “a little complicated” because she and the guy had mutual friends and had known each other a while. She also said she would be at a party thrown by my and her mutual friend (who set us up in the first place) and “maybe I’ll see you there?” I still thought this was a nice form of rejection, but I don’t know this girl very well and was a little puzzled why she’d offer up any details beyond “yep, still seeing someone.”

Maybe she just isn’t comfortable rejecting someone. Maybe she’s looking for something on the side. But if I had to bet on it — and I’m I don’t — my guess would be that she wants you as an option if things don’t work out with the guy she’s presently dating. Even the pot on the back burner needs stirring occasionally, you know?

I would just go to that party and see how she acts toward me, but I’m not as close as her with the mutual friend and wasn’t invited. So I guess my question for you is when a girl you don’t know very well possibly leaves the door open like that, is it on me to reach out again after some more time passes? Or at this point, should I just assume that if she’s at all interested, she’ll talk to me?
-Mario Lemieux

If you follow up again a month or two later, you’re verging on “creepy guy who always randomly asks me out” territory. Just write her back now and tell her that you won’t be seeing her at said party because you weren’t invited. Then tell her that you’d like to see her if her situation ever clears up, and that she should get in touch when that happens.

What that message accomplishes is perfect clarity, but also a healthy dose of self-respect. You don’t want to get strung along by a series of soft rejections from someone who may or may not be available and may or may not be interested. Getting strung along is NOT just fucking going for it.

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