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Dear KSK,
our fantasy baseball draft is coming up.

Football. You meant to say football there.

which means i have to pick a new “team logo” for this season. is it going too far to use my league commissioner’s DUI mug shot photo as my team logo?

pertinent facts are as follows:
1.) it’s a DUI mugshot photo
2.) the DUI was well over a decade ago;
3.) last year’s league winner STILL hasn’t been paid yet b/c one person in the league is being a deadbeat. so rather than just pay out the 11/12 of the winnings that have already been collected, our league commish insists on collecting ALL the money first, & then paying out. so i’m pretty sure our league is actually a ponzi scheme;
4.) it’s a DUI mugshot photo
5.) my league commissioner is a friend AND he works at my firm, so i’m gonna have to see him every day
6.) it’s a DUI mugshot photo.

i think it’s f’ing hilarious. but… our league commissioner can be kind of an overly sensitive princess sometimes, and does not possess the ability to laugh at himself. so i don’t want to be a dick but at the same time… it’s probably the best idea ever.
please advise,
-Kellen Homer

Regarding #3: Why hasn’t the rest of your league stepped on the deadbeat’s neck yet? Peer pressure/berating your friends gets results.

I’d say it depends on the availability of the photo online. Like, if it’s already showing up in image searches for your friend’s name, it’s fine. But you don’t want to be the first asshole to put it online, because that shit seriously fucks with people lives. Otherwise, I say go for it. Overly sensitive people need to be publicly embarrassed the most.

**********

Dear KSK,
I don’t have a fantasy submission, I’ve been too out of the loop over the years to play fantasy football. but I do have a sex query. I know you’ve addressed these types of questions in the past but I’d like to throw out my situation to see what you think. I’m a 31 year old virgin. In case it makes a difference I was a pretty late bloomer and had only made out with a few girls by the time I graduated from college at 21. Three weeks after that I moved to a Buddhist monastery where I’ve been for the last ten years.

How in God’s name did you end up at an NFL dick-joke blog?

I’ve decided to give life in the world a try and dating is definitely a big reason. First, do you have any advice for meeting people and/or going on dates other than online dating?

Yes. Extracurricular activities such as kickball leagues, running clubs, cooking/bartending classes, and general volunteerism (your local animal shelter likely needs people to help walk dogs). You can also meet people at most jobs that aren’t “Buddhist monk,” though I don’t recommend that.

And also, once dating someone, how/when do I broach the subject? How interested is a single woman in her 30’s going to be in a guy with not only no experience for the last decade but extremely limited experience in his life at all?

“So the good news is I don’t have any STDs! The bad news is it’s because I’ve never had sex.”

I think you may be surprised. A lot of women are more interested in finding someone who’s kind / thoughtful / funny than the perfect dicking. Not that inexperience is an asset, but it’s pretty easy to learn.

I suppose there may be some women who are like, “WHOA! Too much pressure, I don’t want to be your first!” If that happens, just say,”Relax, I’m not going to fall in love with you, I just need to get this out of the way. If it makes you feel better, I won’t even call you again.” Speaking with confidence is sexy, and she will have no choice but to sleep with you in the hopes that you DO call her! Ha ha! She fell for it!

Also, I have set up an online dating profile. Right now it’s just my attempt at being witty and intriguing, but I’m wondering if you would see any merit in having a profile that just comes clean that this is my status and back story and I’m interested in having sex with someone even if it’s a totally one off affair just to get it out of the way.

I would recommend against saying you’re a virgin in your profile. The most important thing is getting your foot in the door.

I’ll link my profile here because maybe that won’t be the biggest mistake I’ve ever made in my life.

I’ve done you the favor of removing that link. If you REALLY want to go splashing around the crocodile pit with chicken cutlets tied to your ankles, you may put the link in the comments yourself.

I don’t know how long I’m even going to be on this dating site, I don’t find it that fun. But if you have any female readers in the San Francisco area maybe someone’ll be interested. I’d like to be in a relationship, but also, as I said, I’d be happy to have someone just give me the best 30 seconds of my life with no obligation afterwards. [Feel free to advise here as well. Do you think it should be with someone I don't know and won't ever see? someone who wants a relationship with me? an otherwise platonic friend who I have a good relationship with but with whom I won't be getting involved (not too far fetched it's california after all)?]

I’d love to hear what you have to say.
-Pussy Monk

Have sex with the first available woman you’re attracted to. Just get it out of the way. One time and you’ll lose the dreaded Scarlet V and become merely “inexperienced.”

One critique of your dating profile, though. The very first thing a prospective date sees on your profile is:

Too smart for my own damn good. Looking for someone who can keep up.

So, a couple things:

1. This may be part of the reason why online dating isn’t that fun for you yet.

2. Would you want to go out with a woman who claimed to be “too smart for her own good”? Would you believe she was super-smart if she bragged about it up front?

3. Your ass spent a decade of prime youth meditating in a forest without ever getting laid. You are not THAT smart.

**********

Dear KSK,
In the spirit of being completely off-topic, I have neither a fantasy question nor a relationship question. I’m on hotel internet so I can’t even offer a sexy pic or Ufford GIF as consolation.

These are the questions that make the mailbag when no one writes in with questions.

Some high school friends are reuniting for Memorial Day weekend in New York. What are some places we absolutely have to experience? Some pertinent information: we’re in our mid-20s, and not completely poor for being relatively recently out of college. Not fans of Broadway shows or clubs. Recommendations on good bars would be much appreciated, as would any notable restaurants or non-touristy daytime activities.
Much obliged,
Xmus Jaxon Flaxon-Waxon

Asking the internet “Where should I go in New York?” is like saying, “I have never seen a movie. Please recommend three.” You’re going to get such a wide scope of responses that you’ll end up with too much information.

New Yorkers deal with the immense size of New York City by partitioning it into neighborhoods. If you’re young and you want livelier nightlife, I suggest staying below 14th Street for food and drink — the East Village and Lower East Side, in particular. The West Village is a little more upscale but also great. If you and your friends were in fraternities or sororities on Long Island or in the Big Ten, then you should enjoy the attractive but bland people of Murray Hill (East side from about 20th and 40th).

So find your little sector (or sectors) of the city that you want to explore, and THEN find the best bars and restaurants in the area. Go to New York Mag’s Dining and Nightlife sections, select your neighborhood, and then sort by “Critics’ Pick.” It’s the best way to filter out the noise.

(Also, if it’s sunny and warm, grab a frisbee/football and go up to Sheep’s Meadow in Central Park. Some of the best people-watching in the city.)

(I also recommend going to Brooklyn Heights/DUMBO, eating pizza at Grimaldi’s, then walking back into Manhattan via the Brooklyn Bridge. A terrific combination of food and views.)

(There are entire guidebooks dedicated to the city for a reason.)

**********

Dear KSK,
Football – What free agent acquisition is most likely to see the biggest jump in production thanks to his new surroundings? Any initial instinct on who biggest free agent bust will be (I’m thinking Percy will be overvalued…)

Well Percy Harvin was acquired in a trade, so let’s just call it “new offseason acquisition.” I DO think Harvin will be overvalued come fantasy draft season, but that doesn’t mean he’ll be a bust. I mean, Fred Davis is a free agent. Chaz Schilens is a free agent. DAVID AKERS is a free agent. Harvin could be completely average (for him) and still outperform those guys in terms of draft value.

The free agent I’m most wary of is Mike Wallace in Miami. Wallace, I think, benefited greatly from Ben Roethlisberger’s ability to extend plays and find Wallace downfield. In the three games Roethlisberger missed in November/December last year, Wallace averaged less than for catches for 26 yards per game. Maybe Ryan Tannehill’s better than the Steelers’ backups, but he’s certainly not Big Ben. I plan to steer clear.

[*Wallace has breakout season*] DAMMIT!

Sex – I am self destructive and stupid. I’ve recently started a fling with a coworker who I work very closely with. We share the same title; however, our team consists of 2 other people and we share a cubicle space. We became close friends a few months ago and discovered we were great drinking buddies. Pretty obvious to see what happened there.

Truth of the matter is we are both fairly intelligent and like minded people who like to talk about literature, politics and real life issues. We share similar tastes, and senses of humor. We’re falling for each other. We’ve both said as much, both drunk and sober.

She’s also married. 

I know, I know. There is no possible scenario where this turns out good for either of us. I’ve brought this up with her and she agrees. However, we keep ending up going out after work or making plans or sneaking in a makeout in an empty conference room.

My question for you and the kommentariat is more of a request. Please outline in graphic detail how horrible this is going to turn out for me so I can visualize it and rally some willpower.
– unsigned

Who’s to say what the exact details will be, what with so many different possible outcomes. You could get fired. She could get fired. You could both get fired. Her husband could find out (and likely will, eventually). She could spin your trysts as sexual harassment to save her marriage (do NOT underestimate what people will do to save a marriage). You could get your nose broken when her husband finds out; your tires slashed, your car keyed. Does he own a gun? You better hope not.

And I write all that ASSUMING she doesn’t have any kids with her husband, in which case you DESERVE awful shit to happen to you. I mean, you kind of do anyway, but at this moment you at least have the opportunity to disentangle yourself with your job and your life intact. If she wants to get a divorce and pursue you, let that be her business.

Think with your head, not your dick. Oh, and try masturbating right before work. That should lower your sex drive a little before the work day.