Date Your Siblings’ Friends: The KSK Sex & Fantasy Football Mailbag

03.07.13 5 years ago 86 Comments


Hello friends! It’s another edition of the KSK mailbag to take you home on Thursday. Discussed this week: dreams about cheating, wedding dates with benefits, Wes Welker, ill-advised sibling pacts, Mallrats-era Shannen Doherty, and severe trust issues GOD JUST BREAK UP ALREADY.

On to your emails:

I’ve been dating a girl for the last few months. Going well, and things are great; it’s a very rewarding relationship, all that jazz. But I have had a few dreams in the past few weeks where I have been straight up cheating on her in those dreams. The first dream was me with Britta from Community, and Shannen Doherty, but Mallrats-era, not her doing TV commercials for online education-era. A one time thing, I’m not too worried about.

But then, the other night, I had another dream. This one was me cheating on her with my ex girlfriend from a few years ago. This is an ex who is married and with whom I haven’t spoken in years. The weird thing is, my new gf is in all these dreams, and usually finds out about the cheating before I wake up.

So, basically, my subconscious is fucked. But I can’t tell her about this, right? I don’t think she’d freak out too much, but it’s been on my mind for a few days now, and I’m still on the fence. Please, tell me I’m a dumbass for even thinking about bring it up. That or someone is Incepting me.
Yours in dick jokes,

Let’s put this in the simplest terms possible: you are considering telling your girlfriend that you have a recurring dream about cheating on her. That is unwise. Don’t do that.

Also, if you’d like your Britta sex dreams to have more detail, Google “Gillian Jacobs stripper Choke.” (It’s not as perverse as it sounds.)


Uffsies (Can I call you Uffsies?),

Ha ha! Sure!

Short question. I’m attending a wedding with a friend who is in the bridal party. Me and this girl were occasional hookup partners (she moved to Korea). Neither of us have a desire to date, but I want to do something nice for her (It’s going to be a very swank wedding and she didn’t have to bring me). I thought about sending flowers to her room before she got there, but she’s flying back the next morning so that would be a waste. Jewelry would probably be a little weird. Any ideas I’m missing (hour at the spa since she’ll be jetlagged?)

An hour at the spa is incredibly thoughtful and kind, and it trumps whatever I might have thought up in this space. You also stand to benefit from her being physically relaxed, so it’s a win-win.

Much appreciated. No fantasy question so here’s Joanna Krupa’s ass

I could go for something a little rounder, but I’m not one to complain about the sexiness of sexy women. So, thank you.


El Capitan,
Football first: Any thoughts on Welker’s value if he leaves the Pats? While most people agree that he’ll be less valuable fantasy-wise without Brady, I’ve seen some sites describe him as a borderline WR3/4 if he lands somewhere that doesn’t have a top-15 QB.

Danny Amendola manages to be pretty valuable without a top quarterback. Welker may not get 100 catches on a new team, but he’d probably still get 75 or 80, which is still more than your average WR 3/4.

Sexy time: My younger sister and I have a good relationship. A long time ago, we made a pact not to hook up with each other’s friends, and we’ve kept that through going to the same high school, college, and now living in the same city.

That’s stupid. Having a younger sister is a super easy way to meet girls. The two of you should be facilitating each other’s dating lives, not cock-blocking each other.

My dating situation has been in flux lately as I get into my late 20’s – I’m looking more for a meaningful relationship to replace the casual dating/banging that has filled the last few years.

I don’t need to read your email. Go ahead and date your sister’s friend.

A few months ago, a group of us were drunk and partying and my sister’s best friend (recently out of a long relationship) hit on me. I resisted, but she told me that my sister broke our pact a few years ago on a large group road trip with one of my closest friends. (I remember that night, they stayed up later than everybody else, drinking and talking, but both swore nothing happened (although I know my sister had a crush on my friend).

Who gives a fuck, your pact is stupid.

I trusted my buddy, as he has a younger sister himself and understood my situation more than anyone.) In my drunken stupor I was angry, wanted some payback, and was with a hot girl who was into me. We hooked up and it was awesome, but the next morning we promised not to do that again and to keep it a secret, which we’ve done. (As a side note, a few days later I confronted my friend buddy about what I’d heard, and he denied it again. At this point, either one of my closest friends lied to me twice to my face, or this girl made it up to make out with me. Still have no idea who is telling the truth.)

Here’s an idea: let adults sleep with other consenting adults if they feel like it.

Either way, I’ve spent time with this girl since that night, and it hasn’t been awkward, and we’ve actually had fun together. I’ve got to know her now that she comes out more (i.e. not in a long-term relatinoship sitting at home with the boyfriend), and her and I get along really well. She’s looking for the same things that I’m looking for, and in any other situation I would ask her out without thinking twice…execpt for the fact that she’s my sister’s (best) friend. Last weekend, we were at a bar with a group of friends, drinking and dancing. We were making eye contact all night and she routinely turned away other guys to continue talking and dancing with me, which I’ve read as her being into me.

My question – I like this girl. My sister and I have both turned down hooking up with each other’s friends, but I like this girl and am actually interested in dating her, not just getting laid. I’m kinda lost here Captain. Do I ask this girl out on the side to gauge her feelings before broaching it with my sister? That way, if it’s nothing serious, we can drop it and continue just being friends. Or, should I ask my sister permission (to keep my relationship with my sister honest?) Do I even bring up the fact that we’ve already hooked up, knowing that it’ll open up more questions about whether she hooked up with my friends?

Thanks in advance for your help.
-Brother from the Same Mother

Talk to your sister. Your pact sounds like the moronic concept for a shitty romantic comedy, and you should dissolve it sooner than immediately. Date her friend.


Dear KSK,
Fantasy: Our league is currently a 12 man keeper league (2 per team) that has been around for 5 years but our commish is pushing to get four more guys mainly because he has 4 more friends he wants to let in. Does something like this allow us to rightfully strip him of his title? Don’t get me wrong, he isn’t a bad guy, but the thought that 16 guys is acceptable leads a few of us to believe that more stupid rule changes are imminent.

My work league had 16 teams. It was dumb. Twelve teams is perfect. If your commish wants a league with the other four guys, he can start a league with them. There’s no need to stage a coup, but it may be wise to build a coalition that’s against expanding the size of the league.

Sex: My girlfriend of 2 and 1/2 years is always on her phone texting to friends family or whoever, and it has always been this way. Unfortunately it is starting to get to me that there is something wrong here with the fact that even laying in bed at night she is doing so. Sometimes it is guy friends that she has known longer than me, sometimes girl friends and sometimes it is family, but truthfully it doesn’t even matter.

I would argue that it kind of matters who she’s texting. I could understand her best friends and family warranting an immediate response, less so her guy friends.

This inevitably got my mind running down all the wonderful possibilities that I really don’t want to deal with and it got me worked up for a few days. She said I wasn’t myself, asking what she was doing and where she was and treating her phone like a leash but I can’t bring myself to drop it. It got so bad that the other night I drove past her place at like 2am and there was a car in her driveway and I nearly died.

The sad part is, that I trusted her completely and had no reason to really doubt her whatsoever, but the constant availability to everyone else while we would do stuff drove me nuts after so long. Now because of that, I have created an even bigger problem by both violating the trust of someone I love but also maybe actually finding out something I don’t really want to be true, even if it is.

We haven’t spoken in 4 days because she was pissed about the way I was acting and obviously we know why I haven’t contacted her. My question is how am I supposed to handle this? I don’t know whose car it was, but asking about it exposes that I don’t trust her and have become someone I don’t really like at this point either. Is there really any good way to do this? If I am right about what I saw, I’m done anyway, but if I am wrong then I become the bad guy.

There are three big red flags here.

1. Constantly texting other people instead of looking at the person you’re with is rude. I wouldn’t do it to an acquaintance, much less the person I love.

2. You don’t trust your girlfriend.

3. Dating her has made you someone that you don’t like.

Age and experience tells me that your relationship is fucked, but there may be a slim chance of saving it depending on how well you two communicate (and, of course, whether she’s having sex with other people). So lay it all out for her: explain how her texting makes you feel, tell her what you did (and what you saw), and apologize for your actions. And then try to feel out if this is a relationship the two of you want to save. If so, then you get to have a whole OTHER talk about the behavioral changes the two of you need to make to prevent this from happening again.

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