‘Can I Date My Friend’s Ex?’ The KSK Sex & Fantasy Football Mailbag

07.11.13 4 years ago 51 Comments

If you get this reference, I am so, so sorry.

I got married a year ago this week. A few days after the wedding, I wrote about how my wife and I endured a bout of food poisoning while traveling home from Mexico. It was well-received, but it ended somewhat abruptly because I had to publish it during a layover on a cross-country flight for work. And ever since then, that essay laid out my wife’s sickness in great detail while barely mentioning my own.

So, to commemorate the occasion, I’ve updated and expanded the story to include the gory details of my own illness. I hope you can find the time to read it and laugh at me. Otherwise, please continue with today’s mailbag, which skews slightly towards fantasy football. It’s just that time of the year.

I previously wrote to you about my idiot friend Greg and his rebound relationship with his hot, younger girlfriend. The good news is that they’re still together and going strong. The bad news is that my idiot friend Greg showed his hot, younger girlfriend my question and your answer in the Mailbag, and now she hates my guts as she thinks I don’t think very much of her. While she’s wrong (I called her “hot”, “younger”, “more grounded than her friends” and said I was happy for him), I have no quarrel with her. However, I think my idiot friend Greg was a real idiot for showing her the Mailbag, since he had no way of knowing how she would react–that’s part of the charm of these hot, younger types. While my idiot friend Greg knows he is an idiot for showing his girlfriend the Mailbag, can you please confirm that my idiot friend Greg is an idiot?

Yeah Greg, what the fuck? “Oh, hey, here are some people talking about me having a mid-life crisis and topless Jacuzzi parties on ecstasy with my new young girlfriend and her wild friends! I should probably show her this discussion!” As we say in the Marine Corps, “ENGAGE YOUR BRAIN HOUSING GROUP!”

Hot Young Girlfriend: if Mark continues to be an idiot and shows you this mailbag as well, give Mike some slack. He’s old and married, and thus confused by the idea of sexy young people enjoying casual drug use and mind-blowing intercourse. If you feel judged, it’s only because ALL old people judge ALL young people. I’m 34, married a year, and already I can barely hang out with my twentysomething single friends from work. “Why are they so loud? And laughing so much? Pull those pants up.”

So be patient with Mike. He thinks of you as a beautiful curiosity.


Oh Captain, my captain,
Fantasy First; I’m managing a 12 team league that has decided to switch over to a keeper league last year, and due to several REALLY overenthusiastic owners (myself included) we developed a rather byzantine set of rules for valuing keepers. I wont bore you with the details, but its more complicated than just “lose the pick you drafted the guy at,” so the free draft provided by the website we’re going with isn’t going to work for us. I don’t know why I’m still surprised that ESPN disappoints me.

It’s been doing that since AT LEAST 2006. It’s why sports blogs became a thing.

Anyway, it won’t let me selectively delete certain draft picks to take into account the special keeper valuation rules we’ve decided upon, it insists upon valuing keepers like everyone else. Obviously, an offline draft is the simplest cure for this, but the league is spread out across the great state of California, and many of the owners are unwilling to come to San Diego for a draft weekend vacation. So, my question is, do you know of any software out there that will let me run our draft the way I want to online, or at least something that could keep everyone keyed into an offline draft without having to have a conference call or massive skype conversation going on?

I know of no such software. However, Yahoo’s fantasy football has that function. Ditch ESPN, there’s still plenty of time before the season.

Sex: Sorry, no real question here. I’m happily married to a very pregnant woman and deeply buried in Bar studying so I don’t have time for it anyway. I’ve attached a vintage picture of Jennifer Connolly without very many clothes on,
ESPN, go fuck yourself


Several years back, when she and Paul Bettany still lived in my neighborhood (Park Slope, Brooklyn), I ended up eating lunch at the same cafe as them. This was just before she got so frightfully skinny, and I can confirm that she is jaw-droppingly gorgeous. Surprisingly tiny, but one of the most beautiful faces I’ve ever seen. Very difficult not to stare.

(Bettany, in contrast, is surprisingly big — six-three or six-four — and he kind of galumphs around by contrast to Miss Perfect up there. Lucky son of a bitch.)


Dear Caveman,
Happy NFL doldrums.

Not doldrums. Merely the calm before the storm. A calm that has frequent updates about a star tight end who allegedly murdered a guy, so, you know, we could be worse off.

Fantasy first- What are your recommendations for larger leagues? I’ve had a 12-person league of Vikings fan-friends the last number of years but we added a bunch of guys who we’d love to find a way to incorporate this time. Problem is I’ve never had good experiences with 14-person leagues, let alone 16 or 18 (if it comes to that).

I was in a 16-team league last year. Do not be in a 16-team league.

We typically play with 10 starting (QB, RB, RB, WR, WR, WR, TE, Flex, DEF, K) and four bench spots. One thought I had was eliminate the flex and two bench spots, meaning we could add four teams and still maintain nearly the same depth of quality–although obviously this would change the add/drop dynamics significantly. Could also drop one of the WR slots? Would love any thoughts/innovative ways you’ve come across to make this work.

From what I’ve seen, in a 16-team league, there are really only enough decent players for four starting RB/WRs. I’ve seen 2 RB/2WR, and I’ve also done 1 RB/2 WR/1 Flex, which provides some flexibility but dramatically impacts your drafting strategy.

Sex/whatever- Let me be the 3,000th person to say to say your official break-up guide works. Three quick questions:
1. Do you judge people if they get a new girlfriend who’s the same ethnicity/body type as their last one? I feel weird about it, especially since I didn’t think I had a “type.”

I try not to judge people at all, unless they’re wearing Toms. Date whoever you find attractive and likes you back.

2. In the early stages of a relationship, the woman tells me her mother is going through chemotherapy. Obviously I need to be as supportive as possible, but any particular tips for something so serious this so early?

Nope! A lot of hugs?

3. She’s completely football illiterate but (at least at this point) willing to learn. What’s the best way to try to interest her without overwhelming, toward the idyllic and unlikely goal of her actually enjoying it as much as I do?

Thankful Emailer

For a lot of NFL neophytes, fantasy football is the best way to develop an interest in the league. If your girl has a competitive streak, this may be the way to go. She can study up on the players before the season starts, and having a fantasy team will give her an automatic rooting interest in almost every NFL game.

If that’s not really her style, you can always show her handsome players (WELKER’S DREAMY!) to give her guys to root for. I’ve done this with the U.S. men’s soccer team and my wife. She hasn’t taken to watching games with me, but she IS devastated that Carlos Bocanegra lost his spot on the team.

Personally, I wouldn’t push her one way or the other. If she’s interested in your interests and picks the game up, cool. You get to watch your favorite sport with someone you also have sex with. If not, then Sundays can be your day to hang out with friends and watch the game. Time with the guys becomes rarer the deeper you get into a relationship, so it can be nice to have that programmed into your schedule.


Hello Captain!


I have a lot to inquire about fantasy wise so I am skipping the sex question and including this picture which depicts where I would immediately go if I had a time machine and a get out of jail free card (I’m happily married).


Ah, trashy era Christina Aguilera, we hardly knew ye. Let’s add a GIF for good measure:

FF! Our league is entering its fourth year, and we drafted last year knowing that we would be starting keepers this year. The agreed upon format was that you could keep anyone drafted in rounds 3 or later for a two round penalty this year. As we are getting ready to prep for the draft this year a few issues have come up with this format I would like your advice about.

Issue 1: We have always drafted in a snake format generated in a random order about 30 minutes prior to the draft beginning. We are a 12 team league and we usually get about 7 or 8 guys together live and the rest is a mix of remote live drafters and auto-drafters. Due to the introduction of keepers this year some people in the league feel that a reverse order of last years standings draft order is appropriate. I understand the NFL works this way, but with fantasy there is so much roster turnover I don’t really see how it means enough to order the draft on it. As such I lean towards keeping the random ordered snake draft. What are your thoughts on this? 

You can keep random order, but you need to determine that random order BEFORE keepers are decided, not 30 minutes before the draft. With that two-round penalty for keepers, people need to know whether or not their third-rounder is going to cost them the #1 overall pick.

Keeper question: The keeper options I am considering – I get to keep 2 for the cost listed. Peterson for a 1st, Colston for a 4th, Demarius Thomas for a 5th, RGIII for a 6th. Peterson is a lock right?


I’m super worried about RGIII who through most of last season figured to be sticking around on my squad (Did I mention I lost my 1st round playoff game?). I’m thinking I go with Thomas and snag a QB and another RB in rounds 2-4. I could also keep Peypey for a 4th but that’s just crazy. Right? (Standard PPR but 6 points for passing TD’s).

Love the column, keep up the great work.
LeSmarius McSkittletron III

Whoa, Manning for a 4th in a six-point passing TD league? I’d say that trumps keeping Demaryius, which is a shame, because you want that top-flight WR in a PPR league, plus the QB-WR double-tap is nice for touchdowns. I say keep Peyton for that 4th, and use rounds 2 and 3 for a WR1 and RB2/WR2.


O Captain My Captain,
Fantasy First: My league switched to an auction last year, with $200 budget (standard scoring). The only keeper I have right now is Doug Martin, who would cost me $55 to keep ($50 original price, $5 keeper fee). As a general matter, how much is too much money to devote to one player on your team? I know you’ve mentioned Martin is probably a top-5 RB, but is it a good idea to tie up 1/4 of my payroll on one player?

Standard caveat: I shy away from auction leagues myself, but I don’t think I’d go for for broke with Martin. As I noted in my 2013 fantasy football preview with Anita Marks, the first round is stocked with more quality running backs than any time since Mike Shanahan introduced running-back-by-committee. If you want, you can watch the whole thing; I’ll give the “tl;dw” below the video.

Basically, here’s a list of running backs I’d be perfectly happy with if I got in the first round: Adrian Peterson, Arian Foster, Doug Martin, Jamaal Charles, Marshawn Lynch, CJ Spiller, LeSean McCoy, Alfred Morris, Ray Rice. I’m not huge on Rice in 2013 — I suspect Bernard Pierce will continue to get a bigger workload —  but that’s a nine-deep list of robust running backs. Let people break the bank on Peterson, Foster, and Martin. I’d aim for Charles, Spiller, or McCoy at a slight discount.

Sex Second: A good friend of mine, Mike, broke up with his girlfriend of six years just about a year ago. They broke up for a myriad of reasons, including the fact they lived on different coasts, one person didn’t want children, etc. He’s now engaged, and very happy (or as happy as you can be while doing wedding planning). His ex just moved to the city I live in, and she and I have always gotten along.


As you can probably tell where this question is heading, I’ll cut to the chase – when, if ever, is it OK to hook up with a friend’s ex? Does it make a difference that he is now in a happy relationship of his own, and that this wouldn’t just be a fling on my part with his ex?

-Bro Code Violator

I’ve never cared for the meatheaded bullshit required to act like you maintain ownership of a person’s genitals after a break-up — as if an ex-girlfriend is a tree that the alpha dog peed on. As with most ideas that fall under the term “bro code,” that attitude is more macho posturing than actual manhood, an approximation of masculinity in lieu of the real thing.

Nevertheless, six years is a LONG-ASS time to date someone. And though the passage of time and his engagement to someone else SHOULD preclude him from getting pissed off, feelings have a way of circumventing logic. Assuming he’s a reasonable person, and assuming you DO hook up with his ex, I think you can expect him to (a) be initially upset, and (b) get over it. Life’s too short to spend your marriage being upset by who your ex-girlfriend is dating.

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