Oh No He Di-In’t! The KSK Sex & Fantasy Football Mailbag

04.04.13 5 years ago 111 Comments

“Iguana make it up to you!”

Welcome to another edition of the Sex and Fantasy Football Mailbag and Guide to New York City. Once again, dear readers, please write in with questions about sex and/or fantasy football. I’m happy to give my opinion on anything, and if I don’t know the answer to something, I’ll try to steer you in the right direction. Our email address is on the right side of the page here. Hit us up.

Your questions:

Dear KSK,

Fantasy: Does Kevin Kolb in Buffalo – just kidding. He sucks.

I’ve been dating a fantastic girl for a year and a half now, living together about 4 months. She’s great. The sex is amazing, we laugh at the same jokes and my family adores her and she loves them too. Ditto her family with me. Problem is, now that marriage has come up, money is an issue. We’re both 28. While I make about $45k, she’s under $30k.

What is she, a fry cook?

We live in a top 5 media market so that money doesn’t go nearly as far as it could in most areas (like Wichita!). I barely get by with all my student loans and crap and she loves what she does so there’s no changing that. As it is, she’s carless, walks to work every day and is still barely getting by. I worry if I marry this girl I’m sacrificing things I want in life (house, vacations, etc) to scrape by. I also work in the burbs and don’t wanna live in the city forever but she needs public transportation without a car. With money being the cause of many divorces it just seems short sited to ignore the fact that I’ll have to pull the weight with an average job.

Average job? YOU’RE POOR AS SHIT, TOO. I’m not even trying to bring you down, because I’m a barely-middle-class schlub trying to get by in a city I can’t afford, but still: what do you think you’re going to do if you’re unburdened of your girlfriend? Buy a house in the North Bay with a $45K salary? I think not, sir. (Aim for Stockton, and then you have a case.)

I’ve also brought up a prenup and got shot down really quickly.

This is a whole can of worms that I can’t go into because I don’t know your history, your girlfriend’s history, or your families’ histories. All I can say is that it’s legally advisable but often practically difficult — a technically smart move that often spoils the chemistry, like betting “NO PASS” at a craps table. So I don’t want to even wander into this territory.

What do I do here? I’ve dated lots of girls and she’s truly special. All things equal, I’d marry her in a second, no doubt, but I don’t know if I wanna give up the things her salary will force us to. Do I move on, bite the bullet and go in without a safety net or insist on a prenup? I figure I have a year or so max before I’m forced to make that call. I truly love this woman but man, I worry this has “bitter, divorced 40 year old man paying half his salary for someone else to live” written all over it.

-Sam in SF

There’s no delicate way to say this: if you make $45K a year, YOUR GIRL IS NOT MARRYING YOU FOR MONEY. You are not a baller. It is extremely unlikely that you’ll find someone better if you break up and move to the suburbs.

Furthermore, don’t try to drop this “I truly love her, BUT…” bullshit on a thinking audience. I truly love my wife, and if she got hit by a bus tomorrow and ended up in a wheelchair for the rest of her life, I’d still love her just the same regardless of her earning potential or ability to bear children. I’m wholly committed, period. And that’s crazy to actually put down into words.


Hey Ufford!
I’m an Aussie, so unfortunately I do not play Fantasy Football and therefore have no question. Please accept this video as compensation:


Sex (kinda): I recently booked flights for a 5 week trip to the States in mid-October (NY, BOS, CHI, MIA, Vegas, SF, SD) and I will be spending the first 10 days in NY. Being a local and something of a legend,

I assume that by “something of a legend” you mean “not a legend at all.”

I was hoping you could give me some pointers on good drinking/dining venues that would enable me and the couple of dudes I am travelling with to mingle with some young ladies.


For the record I will be 25 when I am there, and I am usually pretty good when it comes to women (being a career single will do that), so basically I just need to know where to go. I’m also hoping my accent may help.

It will.

Also any other general tips would be appreciated, but please be gentle, it’s my first time!

Hell I’d even be keen to grab a beer with you at your local watering hole if that’s not weird.
Oliver Clothesoff

First and foremost, I’m always happy to have beers with strangers, but you will almost certainly be disappointed with the Ufford Experience. I’m a decent conversationalist and hold my booze well, but you’d likely find me boring. I’d force you to come to Brooklyn because I wouldn’t want to travel “all the way” into the city, and the bar I’d pick would be some quiet place without any single women because they’re loud and annoying and get in the way of my drinking, and then I’d leave early because staying out late just fucks up my entire weekend. But if all that sounds like a good way to spend one of your nights in one of the world’s great cities, you have my email.

But onto your main question: tips on New York drinking and skirt-chasing, from a man who hasn’t picked up a stranger in a New York bar since  probably 2008. (Parties, yes. The subway, yes. Penn Station, yes. But not bars. By my late 20s, trying to pick up women in bars just made me depressed and cynical.) But hey! You’re a young Australian with a sense of adventure! Go chase those skirts!

So, okay. Here’s Manhattan by neighborhood:

In terms of nightlife, just cross off everything above 14th Street except maybe Murray Hill/Rose Hill/Kips Bay. Now, Murray Hill for someone like me is AWFUL, because it’s a bunch of Long Island bros and advertising or finance guys who were in fraternities at Big Ten schools — every dude wears a button-down shirt and a North Face fleece. For someone like you, however, this can be a great place to go, because the women are attractive and predictable.

For my money, though, the best places to go out are in the East Village/Alphabet City/Lower East Side. Check out the recommended bars and restaurants in New York Magazine for those neighborhoods, and you’re certain to have a good time. But, again, it’s a gigantic city, and I really only know two of the five boroughs well (not that anyone should go to Staten Island, but still). There are entire guidebooks and websites dedicated to this city, blogs dedicated just to the food scene… if you’re traveling halfway around the world to get here, make sure you’re thorough in your research.

Oh, and spend $20 to go to MoMA, the collection will blow your mind.


Football: My team has increasingly gone downhill the last 4 years. From runner up my first year, (4 years ago) to out of the playoffs last year. I am sure this is due to being a much better more productive human over the last few years, and thus having less and less time to read about fantasy football. What are the best, most time efficient ways to do research for my next fantasy football draft?

Watch my web series KEEPERS!

I don’t think there’s an efficient way to do research, except to not do it all until right before your draft. The research is a time-suck, a rabbit hole of information and opinion that produces no clear picture. The best thing you can do is make a sensible, ordered list of players right before your draft. And most importantly: make sure you have the most recent health updates. You don’t want to waste a second-round pick on RG3 if he’s not coming back until November.

Sex: I have been casually dating a great girl off and on for little more than a year. She is smart, funny, nice, actually a fun adult and not bitchy in any way. She has a great job, is really fun in bed, and overall has all the qualities that any guy would want in a girl.

There is a problem. She has one eye and is legally blind.

She is really attractive except for her eyes, which to be honest look really bad. Like “walking down the street random stares from strangers” bad.

“She’s really attractive, except for her face.”

The issue is this: while I am increasing comfortable with and used to her looks, it is really hard to square my self-image as a normal-looking reasonably nice/smart guy with the guy who is with the weird-looking girl.

I honestly care about her, but I have no idea on how to adjust to the situation. I would appreciate any thoughts you or anyone else has on the subject?

Hope this is more interesting than asking about tips on how to best visit NYC.
Drunken Koala

Don’t overthink this one. You either care enough about this girl to not give a shit what other people think when they see you with her, or you don’t. HINT: You can usually tell if you care enough if you don’t spend more than a year “casually dating on and off.”


Hey, it’s a lady reader!

Dear KSK,
I don’t have a fantasy question, so here is a gif of Kate Upton giggling about something.

Probably about a joke I told her. We have a natural, easy chemistry.

Sex question: I got out of a serious relationship a few months ago. It was one of those particularly shitty breakups where nothing was wrong, but he moved to Dallas (1,000 miles away) after he graduated from our grad school program in December. I wanted to do the long distance thing, but he was way smarter than me and said it wasn’t a good idea. I’ve been pretty torn up about it, but I’ve been taking your general breakup advice (your advice is way better than any on lady sites, btw) and have lost 10 pounds, started up some hobbies again, cut off contact, etc.

Even still, nothing really helped that much until I started hanging out with a new guy. We’ve hooked up several times, the sex was great — and just that had done more to put my ex behind me than anything else. UNTIL, last weekend, I was out at a bar with some friends and he was there with a different girl. Totally fine, we’re not dating, and I don’t even want to date him. But, he came up to me and introduced her as his girlfriend.

He informs me later that he has this long distance girlfriend who lives several states away and they’ve been dating for two years. I had no idea. He’s always been the one to initiate hanging out/hooking up, we don’t have a lot of mutual friends, and he doesn’t have any pictures of her at his house or anything.

He’s still texting and trying to hang out. I’ve been blowing him off so far, and I haven’t hung out or hooked up with him since I found out about the girlfriend. I guess I’m wondering if there is a way to still hook up with him so I don’t have to think about my ex without being a terrible person?

Not really!

Part of me is sure that it’s an awful idea, and the other part of me is like “well, anything that makes you forget about the other guy can’t be that bad.” Basically I am swinging between the extremes of “You don’t owe this girl anything, go have fun!” and “you will be a huge slut if you hook up with a dude that has a girlfriend.” Having written all this, I’m pretty sure I’m a terrible person. Thanks for your help/tough love.

You are correct in that you owe that girl nothing. But if we treated all strangers like garbage just because we owed them nothing, the world would be a pretty shitty place to live. And I don’t want to get too entangled in the web of feminist ideals, but I’ve read enough Jezebel comments to know that being a woman in the dating pool is hard enough without other women fucking you over.

And let’s talk about this guy who’s not only a big enough asshole to cheat on his girlfriend, but also shamelessly brazen enough to introduce his unknowing fling to her. He has to have balls like kettlebells to just assume that you weren’t going to say, “Oh, you didn’t mention you had a girlfriend all those times we fucked.” (NOTE: that would have been awesome.)

As you wrote above, The Matt Ufford Post-Breakup Plan works. Please note that fucking someone who’s in a relationship is NOT part of that plan. Not only is it bad karma, it encourages this asshole that his asshole behavior is okay. Have some self-respect; there are plenty of guys without wives and girlfriends who will be more than happy to have sex with you.

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