Old Questions Answered In New Ways! The KSK Sex & Fantasy Football Mailbag

04.05.12 6 years ago 84 Comments

Good news and bad news, folks. The good: the mailbag’s done early today! Yay!  The bad: the mailbag is slightly shorter than usual because of it. Sorry.

Nevertheless, I think we dig deep into a couple of good questions regarding cheating, drafting on the turn, a certain STD (read on to find out which one!), cutting ties with exes, and the worst case of “friend zone” I can ever remember answering (see the banner image for a preview). Let’s get into it.

Dear Mailbag Master,
Sex: While this is not a personal situation of mine, I wish you would arbitrate the matter. My girlfriend’s roommate (let’s call her Michelle) wanted to take a cross-country flight to see her best friend over the summer. HOWEVER, her best friend just so happens to be a guy who she used to hook-up with and still has feelings for. Even better, this guy has a girlfriend, and he already cheated on her once early in the relationship with Michelle.

Whatever Michelle wants to do: NO.

The girlfriend found out that Michelle wanted to visit and stay with her boyfriend while her and all of his roommates would be gone for Summer break, and told him that she most certainly COULD NOT visit. He then passed along the bad news to Michelle and she was LIVID and in tears. This girl has no right to be upset, right?


Is there any possible situation where it’d be alright to visit a past flame (no matter how good a “friend” they might be) and share a room AND a bed?

No. And old flames aren’t “friends” — they’re old flames. Occasionally, you can move towards a platonic relationship where you’re happy for the other person’s success in employment and love, but this generally isn’t the case when you’ve cheated on your present girlfriend with said old flame who wants to fly across the country for some quality time in bed with her “friend.”

What I’m saying is, Michelle is seriously retarded.

Football: A few of my friends have recently thought about “retiring” from the league due to new commitments they didn’t have last year. One of them became a father, and some of them are starting post-grad schools and think they won’t have enough time to put in the effort they think they need. Mind you, none of them have ever won this league in the 5 years it’s been run. As the commissioner I’m going to stall as long as I can so that they can realize that it only takes 5 minutes to set up your lineup. My question comes if they do decide to quit for good. Is it my job to find people to replace those who leave, or should it be the responsibility of those who leave to find their replacements?
Thanks Again,
Clearly Confused

They gotta find replacements. I mean, they don’t HAVE to — it’s a fantasy football league, not the year 1863.

/crosses “Civil War draft joke” off to-do list

But they’re already abandoning an incredibly simple method of interacting with friends; they could at least have the simple human decency to find an upright person to take their spot.


Hey Captain,
FF: Don’t have a pressing fantasy question, but I’m curious about your thoughts on draft position. When you pick later on during the snake, do you shift your strategy? Last year I picked 10th out of 10 and was extremely tempted to gorge on WRs by taking both Megatron and Andre Johnson. I didn’t end up doing it, making this question much less interesting, but I am maintaining in the face of continued mockery that it COULD have worked out well.

Not with Johnson’s hamstring.

Do you see any unorthodox pairings this year that might be good value for someone drafting at the turn?

I really don’t like drafting at the turn. Even when you have that first overall choice, it’s a long-ass wait until pick #24 (or 20, in your league’s case) for your second player. I’m much more likely to reach for a player I want when I’m on the turn, and that’s not good strategy.

However, in a ten-team league, drafting at the end of the first round isn’t a bad spot at all. You’ve got a great opportunity to draft a great QB/WR combo that will end up being a safer bet than most of the running backs available in the middle of Round 1. At nine or ten overall, you’ve got an outside chance of Calvin Johnson or Aaron Rodgers being available. Okay, probably not Megatron. But a boy can dream, right?

Sex: Not to get all the-bad-way intimate on you, but I recently went to the doctor because I had some mild skin irritation down in the nether regions. It didn’t seem like a big deal, but whatever, I have good health insurance so I got tested. Lo and behold, I am positive for HSV-2. Fucking herpes.


This shocked the shit out of me. At 25, I’ve only ever had sex with a few people, and I’ve always used a condom. I have no symptoms besides the above. Now, there are a few silver linings. I’m probably not all that contagious — due to my lack of gross-ass blisters. You can apparently take drugs to lower the odds of passing it on even further. And it’s more common than I had thought (though most have no idea they have it).

These things are all true. Also, the chance of outbreaks drops sharply about a year after infection. So while you WILL have herpes the rest of your life, it won’t necessarily affect you the way you think it will. Kind of like Magic Johnson’s HIV.

But the obvious and crushingly terrible downside is that I now have to tell people I want to have sex with that, “Hey, so, there is a non-zero chance you will get an incurable disease if you keep going.” I am going into a depressed kamikaze tailspin just thinking about it. I can’t even FATHOM how that conversation will ever go non-horrendously, much less, you know, intercourse. What the fuck do I do? Not that I have many random hookups, but is this the end of that happy possibility forever? When do you tell someone something that… off-putting? Should I only date people who have this condition that even I think is kinda gross? Can you talk me off the goddamn ledge?
– Apparently It’s Not Courtesy That’s Contagious

We revisit the herpes question every couple months in the mailbag every couple months, and the answer is always the same: it’s not as big of a deal as it feels to you after getting the diagnosis. Here’s what Drew wrote back in 2009 when a dude wrote in about hooking up with a girl who admitted she had herpes:

At this point, it’s less a disease than a cool genital accessory (oooh look! Spots!). She’s right about it not being that big a deal. If you use a rubber and never hook up during outbreaks, you should be fine. But you should ALWAYS wear a rubber, because the truth is that herpes can indeed spread even when she is not breaking out if you aren’t using protection. CRIMINY! Sly little virus, that herpes…

The real issue is down the road. If you end up getting married and wanting to have kids with this girl or something, at some point you’ll have to risk riding bareback. Is it worth the occasional breakout of dick spots to have a happy relationship with a woman you find extremely attractive? I say yes. Getting a hot girl with herpes is like getting a Corvette at government auction. THAT’S GOOD VALUE FOR YOUR PENIS!

Personally, I think Drew’s underestimates the “spots” but overestimates the chances for infection. Regardless: it will be okay. I can’t imagine that the “I have herpes” conversation will be fun, but it will be a lot better to get that off your chest BEFORE sex than to be the kind of weasel who doesn’t mention it.


Good Day CC,
Football: You think with the Bills adding Mario Williams, Mark Anderson, getting back a healthy Kyle Williams, and having Marcel Darius in his second pro year actually translate to wins? The two Superbowl teams had shitty defense so I’m not to sure how improved the team is as a whole BUT the Giant’s line is awesome.

I’ll be convinced the Bills are a real team when their Ivy League quarterback turns in a solid season from start to finish.

Sex/Relationship: I just broke up with a girl I’ve been dating for just over a year in the same city and for about 6 months long distance before that. It sucks. I’m best friends with her brother (that’s how we met), love her family, shes smart, hot, funny and has a great job. I’m still hopelessly in love with her but it just wasn’t working anymore. She has some anxiety and depression issues that she wasn’t dealing with and it began affecting our relationship a ton when she got forced to go on the overnight shift. It was stressing me out, depressing me and just consuming my thoughts so I needed a break. The point of this break is to let her focus on herself, get healthy and possibly resume our relationship at a later date.

I moved from Southern California back to Rochester in part to be with her but mostly to be with a family member that got a pretty grim health diagnosis.

That’s bad.

That particular family member is doing very well (in remission) which I am very happy about.

That’s good!

However, now that I’m single and closer to 30 than 20 with a shitty job in Rochester I feel like the last year took my life backwards about 4 steps.

That’s bad.

I have been working on fixing the job thing by actively looking for new opportunities.

That’s good!

“The new opportunities have potassium benzoate.”

“That’s bad.”

While looking, I asked my former market director in SoCal for an employment reference and he told me just to come back out and work for him again. It’s super tempting but I don’t want to keep uprooting my life. I also know that if I leave I am not coming back, there’s no chance of us rekindling our relationship, I’ll miss my family and longtime friends. If I stay, there is no guarantee of us getting back together, not as many career opportunities, no sun, no fake boobs. If she gets healthy and we do end up back together I’m positive we would be on the path to getting old and fat and having a couple wiener kids ruining our lives for 18+ years. That’s a BIG “if.” Any advice/insight helping me make a decision would be much appreciated.
Knifey McStab

So… stay unemployed in Rochester, N.Y. for the possibility that things will work out with your ex who’s dealing with depression and anxiety, or move back to southern California for your old job and date women who spend weekends on the beach. This is the choice you’re having trouble with.

Love is a wonderful feeling, but it can also make you stupid. I’m sorry for being more pragmatic than romantic, but there’s more than one woman you can spend the rest of your life with. I’ve dated a couple different women that I thought I could marry, and when I look back at those relationships, I generally think two things: (1) “Aw, kind of a bummer it didn’t work out,” and (2) “You know, I’m a lot better off with who I ended up with.”

Some things are meant to be, and some aren’t. If it were my decision, I’d put my own happiness first and move to California. Later, if my ex got her mental state together (depression and anxiety often get worse, not better) and took a job in SoCal, THEN I’d start thinking, “Hey, this could really work.”


Dear Suppliers of Dick Jokes and Sexy Fridays:
Fantasy: My league’s switching to a keeper format, and I only have three options even worth considering: (1) Demarco Murray for an 11th; (2) Dez Bryant for a 3rd; and (3) the 49ers Defense for a 13th. I’m leaning towards keeping just Murray, but there was a huge run on receivers in the third round last year (Fitz, Nicks, Wallace, Wayne, DeSean), and the 49ers D is pretty damn good. So, should I just stick with Demarco? Is Dez worth the price? Is it nonsense to keep a defense?

Murray’s a no-brainer. As long as the ‘Boys have Miles Austin, Dez Bryant’s not worth a third-rounder. Hell, Laurent Robinson finished the season as a better fantasy option than Dez. I might consider keeping him for a fourth-rounder (definitely a 5th), but a 3rd is simply too valuable.

As for the Niners D… why not? You know it’s gonna be a great defense in a weak division, so you may as well keep it. What else are you going to get for a 13th-rounder? A 4th-string running back? Randy Moss?

Sex: My sophomore year of college, I fell pretty hard for this girl. She was a freshman, knew my roommate from home, and stayed at our apartment most weekends. We seemed to really hit it off; so, I told her how I felt. She turned me down. After that, we continued spending time together, and she continued to be gorgeous and hilarious. So, I went for it again. And she turned me down again.

Because  men are stupid and women are needy attention vampires.

We kept hanging out after the second rejection, but I did my best to move on. Eventually, it worked well enough, and we got along just fine. She transferred to a new school for the next year,

Good riddance.

but we kept in contact, occasionally exchanging phone calls or meeting with each other.


It’s about five years later now, and I ran into one of her friends at the bar. The friend tells me that this girl started to fall for me after she turned me down, regrets never giving us a chance, and still talks about me along these lines.

Yeah, she fell for you so hard that she transferred schools and never hooked up with you even though you kept meeting with each other.

/bangs head on desk

PLUS, she just finished school and moved back into town.

Fucking yay.

My interest was piqued; so, I called her. We met at the bar, things went well, and she offered to come with me when I told her I had to get going. We came back to my apartment, had another drink, and went off to my room. Before things got anywhere of substance, though, she says she’s happy this is finally happening, but she’s exhausted and needs to get to sleep. I was, you could say, pretty damn confused.

The next day, she texted me to say what a good time she had and that we need to hang out again soon. She’s beautiful, hilarious, and has been my ideal girl since I was 19 (despite the next sentence). But, she’s turned me down several times in the past, started to like me only after I moved on, and left me fairly confused the last time we hung out. Is it a bad idea for me to get back involved in this? Should I ignore the past considering we’re both adults now and a lot of time has passed? Or is my hesitancy here just my pride saying not to give this girl another chance after she turned me down back in the day?

Ordinarily, I’d say tell this girl to fuck off, and then let her be some other poor sap’s problem. But HELL, at this point I’m just kind of curious to see if she’ll actually sleep with you, or if she’s just hellbent on seeing how many times she can play Lucy and whip the football away before you can kick it. I mean, after five years of leading you on and leaving you hanging, forget pride. That train left the station years ago.

I say fuck her and never call her again. I doubt you’ll follow through on that, but you’ve certainly earned that heel turn.

Everyone other male on the planet: don’t be in love with a girl who likes you as a friend. You’ll get played every time. EVERY TIME. Stop it.

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