On Trust and Break-Ups: the KSK Sex & Fantasy Football Mailbag

02.21.13 5 years ago 51 Comments

Hi everybody! Sorry for the slightly delayed mailbag today. After a lifetime of 20/20 vision, advancing age and years of blogging have made me near-sighted, so I had my first vision test in eight years today. And if you go the better part of a decade without getting your eyes checked, optometrists can be pretty persuasive about needing to dilate your pupils to check inside your eyes. So I spent most of the afternoon with blurred vision. It was like being drunk, only with balance and without feeling handsome and funny. I still prefer whiskey.

ANYWAY. On to your questions.

This first one was submitted last week for the Valentine’s Day ‘bag, but I didn’t have room for it. So it’s a bit dated, but he’ll just have to deal with it.

No fantasy for a while unfortunately. How long do you think it’ll be before Trestman gets my Bears in order/or is fired? The organization isn’t typically known for being progressive or especially fast moving so I think he’ll have plenty of time to succeed or fail. People say good things about him but they also said great things about Raheem Morris.


Sexy: So just my luck: I moved to a new town 6 months ago and the pickings have been slim, dating-wise (I work a lot of hours, it’s a weird place to meet people for things other than work), so I’d been hanging out, staying in shape, drinking and partying and taking it easy. It’s all picked up though very quickly in the last week though.

I went on a date this past weekend with a young lady and she was okay (calm, easy going, cute) and we agreed to meet again this weekend when she’s back from a work trip.

Another works at the same newspaper as a friend, is gorgeous, seems to be sexually confident, and kind of a badass professionally and personally. She works around my field so we’d probably understand each other. I asked her out for this week but she’s not free until next. I’m a little excited to see her (and I caught her checking out my linkedin and doing other research so I think she’s interested in me too)

The third messaged me over the holidays on an online dating site and our schedules are finally aligning. She ordinarily wouldn’t be my type but who knows.

What do I want?

The second one, as she’s clearly the one you’re most attracted to.

I’ve been single since I moved and the breakup was at least partially based in seeing what else is out there and growing up a little on both sides. I’m ready for a relationship and it’d be neat to have a partner but don’t want to take myself off the market prematurely.

My question is 2 pronged: A) How can I get as much as I can from this abundance of interest (that is likely Valentines Day-related) without hurting anyone’s feeling or Archie comic-esque shenanigans (while the city has a large population it’s a very small area geographically)?

Don’t even try, man. Because here’s the thing: what if you end up REALLY liking one of the girls? Do you really want to endanger something that could be special by fucking around, just so you can feel cool for dating more than one person? Trust me on this: you’ll need to tell all sorts of white lies to make it happen, and they end up being a huge pain in the ass to keep track of. Just date one person at a time.

B) Can I get it while avoiding the faux sentimentality of the holiday (and the $120 prix fixe dinners that come with it) or do I man up and use this to really impress the date I like the best? My thought is to just throw it out there and say make jokes about it ‘Ok, let’s meet. Hey girl, what’s your ring size?’

Do not joke about that.

‘How do you feel about white doves?’ Present them a card that says: ‘I choo choo choose you’ Thanks a lot,
Eating pizza in his underwear

Welp, too late now! Hope you had a good Valentine’s Day. With one person.


Greetings Certified Purveyors of the Miller High Life,

Football first: I finally nabbed my first fantasy championship last season, and man, that shit felt good. For next season, I can keep the Muscle Hamster for a 5th rounder or Dez Bryant for a 4th. For most of the season I thought I would certainly keep Martin, but Dez was an animal down the stretch, and there’s a part of me that thinks he’s finally figured it out. Thoughts?

Most of my rational bones say Doug Martin is the better value — a premier back for a lower pick — but I have an anti-Buccaneer bias, and with Miles Austin and Jason Witten starting to decline, I see Dez emerging as a top-3 WR next year. I’d probably keep Dez because I like his ceiling better.

Sex next, although it’s more relationship/life advice than actual sexy time. Sorry :(

Here’s my post in a nutshell because I think I might get a little long-winded once I start talking about it: My girlfriend of four years, who I loved very much and thought I would marry and blah blah, left me three months ago. It completely fucked with my head, and I’m having a difficult time moving on and being happy with myself.

Please don’t be long-winded. Please don’t be long-winded.

[scrolls down]


Some probably pertinent background information: This girl was my first long-term relationship, and I also lost my virginity to her.

So you wanted to marry the only person you’d ever had sex with. Buddy, she did you a HUGE favor by breaking up with you.

Neither of my parents finished school because they chose to get married and have kids at an early age, so they raised me to put my education first and typically disapproved of me dating throughout grade school,

Bold parenting stance, that.

so my relationship experience prior to this latest one was next to none. I had some girlfriends, but sex always scared me a little bit, so even though I came really close sometimes, it just never happened.

I met my ex my third year in college. We hit it off right away, and ironically, I had just about lost interest in school and was just all around screwing up, but she saw god-knows-what in me and helped me re-focus and graduate. She definitely was more into me than I was into her that first year of our relationship, and I took her for granted and was a bit of a jerk, but she stuck with me. Time passed and we fell in love and talked about getting married after we both graduated and landed jobs.


That landing jobs part took a lot longer than we expected, especially for me, but those plans remained. Fast forward to nine months ago,

You know what? I’m just gonna delete the rest of that paragraph, because it goes on too long and sounds just like every other breakup where the other person is clearly dying to get out of the relationship. That sucks for you and I’m sorry, but that’s no reason to bore the readers. Back to you:

Now, I’m 24 years old, single and still living with my parents. The latter is less because I’m some bum–I have a well-paying, secure job that, coupled with the fact that I have zero debt and only a few minor bills to pay, affords me the luxury of having a lot of expendable income and quite a bit in savings–and more because my parents are very conservative and traditionally Mexican and believe that sons and daughters shouldn’t move out until they’re married. I started working out and am in the best shape that I’ve been in since high school; I’m spending more time trying to be the best I can be at work and on my hobbies (cooking, playing music, reading, writing); I’m taking dance lessons; I buy nice things for myself; none of this helps. I think about my ex all the goddamn time, my self-esteem is at an all-time low, I don’t know where to meet girls, and even if I did, I wouldn’t know the first thing about talking to them because I haven’t talked to one in that way for four years. I go out every weekend, but I think this hurts more than it helps because there are all these hot girls everywhere and none of them are interested in me at all, and even if I got the opportunity to put my penis in another girl’s vagina, I think I would break down and cry beforehand. HOW DO I UN-SUCK MY LIFE?!

Fuck Love.

Well, you seem to be following the Ufford Plan pretty well — that is, distracting yourself from heartbreak by going to the gym and focusing on creative endeavors, hobbies, and/or volunteerism. There’s a lot to be depressed about during a breakup: loneliness, rejection, longing, et cetera — but the real killer is the surplus of time and emotional energy that your girlfriend used to occupy. Redirecting that into new activities and new friends is the healthiest and fastest way to get your life back on track.

But it’s not an overnight cure. It’s essentially physical therapy. And just like you can’t recover from a torn ACL with a week of resistance-band exercises, you’re not going to bounce back from a four-year relationship in three months. The rule of thumb I generally hear is that it takes half the length of your relationship to get over a breakup. And I know two years sounds like a long-ass time to be heartbroken, but it won’t always be as bad as it is now.

I hate to bring up Swingers, because it was released 17 years ago and got quoted to death throughout the back half of the ’90s (not to mention the awful swing music revival), but there’s a scene that’s useful for any broken-hearted man who’s acting like a pitiful stupid baby (emphasis below is mine):

Mike: How did you get over it? I mean, how long did it take?
Rob: Sometimes it still hurts. You know how it is, man. It’s like, you wake up every day and it hurts a little bit less, and then you wake up one day and it doesn’t hurt at all. And the funny thing is, is that, this is kinda wierd, but it’s like, it’s like you almost miss that pain.
Mike: You miss the pain?
Rob: Yeah, for the same reason that you missed her… because you lived with it for so long.

You go through the ritual of working out and being a decent citizen with interesting hobbies, and you put on a happy face while you’re dying inside. And eventually you’re not pretending to be happy, you’re just happy. Then you meet Heather Graham in a bar and make millions of dollars directing the Iron Man franchise. It gets better.


I would just like to say that an ex bf of mine turned me on to your column and I can’t get enough. You can run with those puns however you please.

Puns, no. But double entendres? Always.

I skip over the fantasy football questions as fast as possible (and for that I have attached a pic of the most attractive female I could find–I’m at work, that’s why she has so much clothing on).

No one need ever apologize for sending me photos of Doutzen Kroes.

I play in a spread league however, and I am TERRIBLE. Every week there is a winner, usually pans out to be about $100 (a $40 season buy-in) and I have never won once. Any advice for picking teams based on spreads? Both college and pro.

I’m shitty at gambling, so no. But I talked to a couple people who do bet on games, and a common refrain was “If a line seems too low, take the points.” Without scrutinizing that too much, I’d have to agree — I thought the Niners were two touchdowns better than the Ravens in the Super Bowl, and the line was only 4 at game time. (See also: I’m shitty at gambling.)

Here goes my relationship story: I have been seeing a great guy for almost a year who for de facto lives with me, though it just sort of happened about three months in. I have no issues with it–except for the fact that I think he’s an alcoholic.

“I have no issues with my boyfriend, except for maybe a chemical addiction that has ravaged families throughout history.”

We met during the summer, when drinking every night was totally fine, it was light out, people were always out and always having a good time. But at 2am, when we were wasted, he would go for another beer. Or a shot. Or anything that had alcohol in it. I called him on it and he said he had some issues with needing to stop, but that because he was aware of them, he was ok, he could keep them in check. My bullshit meter has been going off since then, but I’m rolling with it.

After the summer he most definitely cut back. He is not the type that needs to drink every day, at all. But if I want to stay in on a Friday night for whatever reason (mostly because at 28, I am still a competitive athlete)

he will have the itch to go get a drink “because it’s Friday.”

Yeah, him and like 98% of people who work from Monday to Friday.

He is a blink shy of 30 and I just think he needs to either grow out of it, or go get help. I have stopped going out with my friends because I don’t want him to tag along and get wasted. He sometimes leaves my front door unlocked, or doesn’t have any recollection of what he does. Or wants to take four mile walks to get weed. But like I said, it’s gotten better. Rather than once a week, it’s once a month.

I still have issues with it.

Yet my friends, who used to go out with us, just think it’s normal. “People get wasted, even after 30.” Which is totally true. And I drank enough Jack in college that I am sure people thought I had a drinking problem. But there is something in the look in his eyes that just tells me there is more to it than just having fun. He has had some traumatic things happen to him and I just don’t think he has ever truly dealt with them.

He thinks I keep raising the bar higher and higher, which is definitely something I worry about.

And something that appears to be true. Not that that justifies leaving your door unlocked or blacking out, mind you.

It also makes me wonder if that just means he’s not the guy for me. I wonder if I am just raising the bar so that I have a reason to break up with him. I don’t see myself marrying the guy just yet, but I am also wondering if it will take time.

One other thing weighing on my mind: he’s never said ‘I love you’. They aren’t hard words for him, he tells his mom, his dad, his sister, his aunts and uncles. But he has only ever told two women he has ever been in relationships with. He considers it the last step before getting engaged. He knows it bothers me (I have told him so)–he lives in MY house and has been for the better part of nine months and has never said it while sober. He says just because he doesn’t say it, doesn’t mean he doesn’t feel it, but that to me is such bullshit.


Arrelious Napoli

Before I answer your question, I need to give full disclosure: I have an alcohol habit. I have a couple drinks every night, and while I don’t get drunk very often, I do lean on alcohol to treat an insomnia that is likely tied to PTSD and which I should probably get properly diagnosed and treated with real medication. This is my own problem, and until I feel like braving the VA, it’s on me to manage it responsibly.

But that’s not the point. The point is that my wife doesn’t drink. Like, at all. And I love her and accept that she doesn’t drink just as much as she loves me and accepts that I do (and, as part of that deal, I try not to get so drunk that I black out or leave the door unlocked).

So I don’t think it’s an issue of your boyfriend being an alcoholic (FWIW, I don’t think he is). It’s an issue of whether you love each other enough to accept each other’s lifestyle preferences. And it seems to me that that’s not the case for you.


Dear KSK,

Been dating “Tammy” for 3 weeks

Tammy 1 or Tammy 2?

we seem to do great when we see each other which is 2-3 times a week so far. We’re 25 and 26 years old We seem to be able to talk about sexual history openly and most other things. I’m not quite as experienced as her, she had a MFF threesome a year ago

Ah, Tammy 2 then.

and seems to show some interest in wanting to again, I was going through a drought, but we seem to enjoy similar things in and out of the bedroom. Tammy has told her parents about me already which she said she usually doesn’t cause she thinks this “feels special”, I would be glad to meet them.

Unfortunately that is not why I write in,

Excellent! Thank you for the unnecessary background information!

it is because she lives 45 minutes away and my friend and his housemates live 5 minutes from her and Tammy sometimes hangs out there. One housemate who sleeps with anyone (with pretty good success) was trying to get with her this past weekend, nothing happened but I wasn’t thrilled to see this guy trying, but she is still friends with him. Not worried about him wanting a relationship but I am sure he will try to fuck with her when he is drunk.

Today she told me the housemate invited her over to watch a movie with all them, so I said go hangout with her friends cause I can’t really do anything else. She let me know there was a bunch a people there (I could easily verify with my friend but I’ll trust her) cause she knows I don’t trust the housemate. So do I play this cool, be hard on this subject or a balanced approach which I’m not really sure how to do.

Guys will fuck anyone

There’s no gray area in trust. Anything less than 100% is a slippery slope towards a miserable, broken relationship. And none of that “I trust her, just not the guy who wants to bang her.” That’s the sort of thing needy, insecure people say to obfuscate their distrust.

Also, I think it’s a little early to go into defensive Alpha male mode. I mean, three weeks isn’t exactly the longest relationship in the world; when the horny housemate hit on your girlfriend, he either didn’t know she was dating you, or he was drunk and considered it negligibly short. Yes, that’s definitely dickish, but it’s not outside the realm of typical dude behavior, either.

If you need to make it an issue, let your girlfriend know upfront that you don’t like Horny Housemate, and — should he hit on her again — you’d feel better if she turned him down cold and demanded that he respect your relationship (rather than, say, politely laughing off his advances). Sometimes a relationship involves exposing your fears: all you can do is lay them bare, and hope the other person doesn’t betray your trust. It’s scary, but it makes for better relationships.

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