Frank Sinatra Approves of This Sex/Fantasy Football Mailbag

06.23.11 6 years ago 72 Comments

Whew, sorry about the lateness of the mailbag, as usual. Strap in, everybody. It’s a long haul to get to the end of this week’s mailbag. On today’s docket: Michael Vick, smack talk, group sex, harlots, the 37th iteration of my standard dating tips, Joey Porter, and more. Enjoy.

Dear Copernicus of Copulation,
Fantasy first: I’m in a league with good friends, it’s casual but competitive. One glaring shortcoming is the lack of creative shit talking. Instead of one-liners, my chosen method of shit talk is in the form of weekly press releases. I’m pissed because I put some thought and effort into the releases, but nobody puts anywhere near that effort into their banter. How can I get these guys (who are generally smart and funny dudes) on the Shittalk Express?

“I work so hard at being a dick to my friends! Why won’t they put a little more effort into being dicks to each other?”

For a lot of people, talking shit to their friends is one of the highlights of playing fantasy football. Other people don’t feel the same way. Some folks (me)  just like the additional rush of weekly gambling. Some people are too busy with work or family to dedicate time and effort to shit-talk. And some people wish that the guy who talks smack non-stop would just shut the fuck up and act like an adult.

Now, I’m not saying that all of those possibilities apply specifically to your league-mates, but it seems likely that not everyone enjoys the shit-talking as much as you do. Or perhaps they read it and enjoy it, but don’t feel the need to engage. Last week, one of my buddies bragged that he’d never lost a Words With Friends game, so I picked up the gauntlet and positively crushed him — he resigned after I hit 500 points, and I was still holding the X — so I posted a screenshot of the game on his Facebook wall with the caption “Do you know where you are? YOU IN THE JUNGLE BABY.” I thought it was funny. 

It got zero comments and zero likes.

Internet interaction is often one-way like that — a lot of people consume but don’t engage. Try getting together some of your league-mates to watch the games together. Trash talking in person is a lot more fun — and less likely to be ignored.

Seximus scandalous: I’m divorced and I’m now dating a fantastic woman who is beautiful both inside and out. Bonus, she’s also a divorcee and makes a solid living as a doctor. Everything is right about this woman, everything. We recently had the talk about past sexual experiences, she asked point-blank if I’d had experience in a group setting (she has not, btw). I said yes, and explained that after my divorce I was in an exploratory mood and had an arrangement with a married couple – I didn’t name names. She was amused but not outwardly bothered by it. By “arrangement” I mean that the three of us would plan dates for the specific reason of having kick-ass sex. Nothing gay mind you, but this woman likes a LOT of attention, simultaneously from her husband and me.

“Okay, team. I want a good, clean, non-gay MMF threesome. No eye contact, and no touching dicks. Now go out there and stuff that bird from both ends!”

Now that I’m in a relationship, we no longer have our threesomes (it’s been about 5 months). Outside of occasional sexual encounters, the three of us are pretty good friends. As I enjoy hanging out with them socially, the time has come to introduce my girlfriend to this couple. So, do I tell her before we go out that this is THE couple? If I do so, do I risk putting my girlfriend in a bad spot because we’re sitting across the table from a beautiful woman whom I’ve… well, you know. My girlfriend’s not the jealous type, but that’s no reason to push it. Or do I not tell her at all, hoping she doesn’t connect the dots? She’s very observant, and I’m worried that she’ll figure things out and feel that I haven’t been honest with her. Also, my swinging friends are in professions where this kind of information could be devastating to their careers. One more thing; if she were agreeable, I know that this couple would probably be open to including my girlfriend (she’s fucking hot), but I don’t think I could handle seeing another dude’s dick in her mouth – does that make me a big hypocrite?

Thanks for your advice –

Whoa, okay. Can you maybe ask some more questions next time?

First of all, if you don’t want to see another dude’s penis in your girlfriend, then you’re not going to have a four-way. Period. If the idea of a sexual situation makes you uncomfortable, DON’T DO IT. (Seriously dude, that’s like the first thing parents tell teenage girls.) Is your feeling hypocritical? Maybe, maybe not. A lot of male fantasies are built on double standards, which is one of the reasons why porn is so awesome. Regardless, it’s not unusual for a man to not want to see his girlfriend penetrated by someone else’s penis.

So, given that you’re not going to engage in a foursome, you just need to gauge what your girlfriend wants to know or is comfortable hearing. Personally, if it were me, I’d talk to the threesome couple and ask for discretion on their part — they should be good with it given their careers — and then I wouldn’t tell my girlfriend. If she asked, I’d tell her the truth. And if she followed that up with “Why didn’t you tell me?,” I’d tell her the truth again: because it was in the past, and it’s not applicable to our relationship now.

Honesty and disclosure are good for a relationship, but that doesn’t mean you need to point out every woman you’ve seen naked, or every dick you totally haven’t touched during a threesome.


Dear Cap’n Crunch,
I prefer fantasy first: Is Michael Vick your ultimate late first round pick, or should you reach for him even at three or four if you have it?

Eeeessh. I wouldn’t feel comfortable using a three or four on Vick. In a twelve-team league, I might go as low as 7 or 8 for Vick if Aaron Rodgers went off the board early.

Now for the business: This question is mostly subtlety and not so much straight up sex. I worked with this girl that ended dating a good friend of mine, but initially we flirted a lot and still sort of flirted on the side while she was dating my friend. I have a solid relationship with my girlfriend but this other girl would come out to trivia night with her boy (my friend) and rub her leg up aginast mine under the table and stuff like that.

Stuff like what? Stuff like touching your shoulder when she laughed? Or stuff like putting her tits in your face when she got up to go to the bathroom?

I went abroad this past year (with my lady) and she kept e-mailing me, and when I got home she had sent me in the mail a hand-written note seeing how I was doing, wanted to keep in touch etc. My question is, have you ever seen this angle before? Is she just trying to be friendly or she (as you say) keeping me in the wings? I see her as a real straightforward kind of girl, and I’ve only been in two long term relationships (one for five and this current one for three) so I just don’t know what she’s playing at. Am I getting played?

Making it Happen

The very last thing that girl is is straightforward. Ask yourself this: would you be comfortable with YOUR girlfriend doing flirting with your buddy that way?


Dear Caveman,
Dating: Each of my last 3 girlfriends suffered a sickness or injury that ended the relationship. The first (1.5 years) had been in therapy for years for depression, OCD, and had a overall traumatic past with several “hard hitter” medications to keep her head straight. I finally reached a boiling point when she started accusing me of causing her additional depression and other outlandish made up things. The next (2-3 months) came down with a brain tumor. Her father basically told me we weren’t in love and this was a family matter and he’d like me to leave the scene and if perhaps after her surgery we wanted to reignite things maybe we could (we didn’t). The latest (7 months) tore her ACL playing sports and her stress level exploded and she was boiling over in rage when intoxicated (usually blaming it on liquor). After 3 drunken rages lasting for hours I had to cut her for my own sanity.

Why do all of my partners keep getting sick/injured/losing it?

Because of you, obviously. “WARNING: Dating this man may cause mental illness, knee injury, or cancer.”

These females are all middle class late 20s to early 30s healthy looking girls with professional occupations and health insurance. I’m not the easiest person to date, but I don’t think I cause enough stress to be causing such ailments.

Oh, you’re actually taking the possibility of being a carcinogen seriously. I did not see that coming.

But 3 in a row and I’m starting to really wonder if karma is after my ass or something like that. Its to the point where after I give an attractive girl a quick up/down, I wonder to myself what ailments she might have and include that in my mental assessment. It’s hard to spot the crazy though.

And even harder to tell which ones have bad knees! That’s why you should ask every woman you’re interested in to bring her medical chart with her on your first date.

Do you have any tips for meeting healthy girls with no mental issues, healthy bodies, and non-brittle bones?

Sure. Move to Fantasy Town in Shangri-La. I’m told the Unicorn District has a thriving singles scene.

I was in a running club but it was mostly dominated by socially awkward dudes.


Do I take up yoga? I’m 28 and I live in a medium sized city. There are alot of random attractive females roaming the streets during a workday but what on earth to say to a girl walking in the other direction is beyond me. Or how to break the ice with a cute girl in front of me for my morning coffee.

Stop sweating it. Girls can smell desperation and desire, and it dries their vaginas up. What you need to do is just focus on improving yourself: get a library card and read more / find a new exercise regimen (yoga might be nice; I of course recommend CrossFit to anyone with extra funds and a masochistic streak) / volunteer at an animal shelter / take a class / whatever breaks you out of your routine. After a while — maybe a month, maybe six months — you’ll look better, you’ll feel better, and you’ll carry yourself with something women won’t have noticed before: a certain air of confidence that tells them, “I’d be lucky to have a guy like that” rather than “I bet he wants to fuck me.” When that happens, the girl getting coffee in front of you will be the one to start the conversation.

Football: I’m heated an 8 game season is even suggested. After such great NBA and NHL championships too. Get it together NFL. The owners obviously don’t want to open their books since they are making plenty of money off their investment in buying a team. It infuriates me.
Sick of Sicklings

I will make sure that the NFL hears of your unhappiness.


Dear KSK,
Football first: Ahmad Bradshaw. Hang onto him? Or shop him around?

Every player is worth shopping if you think you can get someone better for him.

Sex: After a long, shitty dry spell for a while when I took a friend’s advice and gave online dating a shot. I lucked out, met a fun girl, and we’ve dating for about two months now. The sex has been great and she’s a blast to hang out with, so i’m happy on the whole. However, during a more recent round of Tumblr-trawling, I found a picture of her beating around the bush rather enthusiastically, along with a link indicating that she spends her free time working actively as a camgirl. I’m curious, and a perv, so I followed the trail, and yes, indeed, she is apparently augmenting her income working as a camgirl.

Hard to believe that a camgirl would turn to online dating.

Now, I don’t have an issue with her doing it

Wait, what? Really?

(as long as the closest she’s getting with these dudes is the distance between modems), but I feel like this is going to be screaming around in the back of my head the next time I see her. Should I let her know I know what she does? Or should I just wait, and see if she decides to tell me? I like her a lot, and I feel like it might screw up the relationship at an early stage to just blurt out “oh I saw you taking pornographic requests online last night”, but pretending I don’t know seems even harder.

Okay, to each his own. Me, I’d have a problem if my woman was taking money from strangers to masturbate on camera so said strangers could masturbate to her. It would be like dating a stripper, only without the good parts (cocaine and body glitter).

However, since you’re more open-minded, why not just talk to her about it? She’s secretly doing something pervy online, you found out because of your own pervy inclinations — why keep it under wraps? If you want to make her more comfortable about the conversation, make it an admission of your secret: “Listen, there’s something you should know about me. I spend a lot of time on Tumblr, and that’s where I get a lot of my porn…” If she doesn’t react to that, then she should be on the World Poker Tour.

One more thing: make sure — like, one million percent sure — that it’s really her, and that she doesn’t have a secret twin or anything. Because EMBARRASSING.


Dear Licensed Professionals,
Sex: I am a 38 year old male divorcee currently in a relationship of 4 months. I have been divorced for 3 years now. The current girl is attractive, funny, and much more sane than the ex wife. Sex has been fantastic and I could be any happier until I recently got a phone call from her. She told me that she is pregnant. All of our sex has been protected although just last week she pulled a condom out of the trash and told me it was broken. This would not have been as much of a problem except the fact that I had a vasectomy at age 33.

Oh man. Fucking BURN! Destroy that cheating harlot!

This is the kind of things that a wife makes you do when she is done having kids. I agreed to this before the relationship started to deteriorate, but this was definitely the start of it. I have kept this secret from my current girlfriend because to be honest, it’s pretty embarrassing. I realize this was a stupid move now.

Are you kidding? If she’d known about your vasectomy she could’ve gotten a secret abortion and stayed with you and kept fucking other dudes unprotected until you got an STD. Stupid LIKE A FOX, maybe.

(NOTE: I’m going to answer this question under the assumption that she is indeed pregnant, and not just saying she’s pregnant.)

As you have probably figured out, this created plenty of problems, all that I’ve kept to myself for around 4 days now. Im the type of guy who likes closure and I would like to find out everything. How do you suggest I go about this without completely fucking up my life, her life, and maybe even the kids life. I also realize there is probably no way this relationship continues.

“Probably” no way the relationship continues? You, sir, must be the chillest man alive. Do you even have a pulse?

Let me put this in very clear terms: women are much more cunning than men. It’s not our fault; our brains are no match for our dicks, and our dicks are terrible at thinking. By not telling your girlfriend about your vasectomy, you have the rarest gift a man can have in a relationship: a position of strategic advantage. So if you want to truly “find out everything,” ask her the questions you want answered without revealing how you know the baby isn’t yours.

Sit her down and say, “I know the baby isn’t mine. Whose is it?” She’s going to try to redirect the conversation — outrage that you don’t trust her, how dare you, why would you say that, etc. Don’t flinch. Stay on point. Ask again and again until she breaks. When you get your information, tell her, “I had a vasectomy! Now get out, whore!”

Oh, also maybe check with your doctor to make sure that you’re shooting blanks. Might be tough to repair the relationship if the baby turns out to be yours by some miracle.

Fantasy Football: Picked up Vick last year so i automatically won. Somewhat skeptical about drafting him in the first round because he is not going to play all 16 games. I usually have good luck in the draft order so who are the top 5 picks this year?
-Max with No Manhood

I haven’t finalized my top five order yet, but these are the likely names I’d go with: Chris Johnson, Arian Foster, Adrian Peterson, Jamaal Charles, and… either LeSean McCoy or Andre Johnson. MJD falls from the top five because I’m worried about the knee surgery he had, and I’ll take McCoy over Ray Rice because he plays in a better offense and seems better at finding the end zone (or at least gets the red zone touches to do so).


This has been bugging me for a couple of years, and I just wanted someone else to weigh in. I got a Joey Porter jersey for my birthday in ’04, and then he was shot in the ass, and I thought, wow, he’s very lucky. Then the Sopranos aired an episode where a “football player” pays a guy to shoot him in the ass to make him look tough. And I am now certain that’s what happened since Porter never, to my knowledge, had a Pacman-type reputation for hanging out with unsavory characters, (alleged) rapists not withstanding. Should I throw out the jersey in shame?

No. Throw it out because he’s a loudmouth jackass, or because he left your team for a conference rival, or because his dogs kill horses, or because you don’t approve of what you suspect is his closeted homosexuality. Hell, throw it out because it’s a Steelers jersey.

Fuck Joey Porter.

As for the other thing – I work in the political field as a researcher. My job every day is to dig up dirt, analyze records, and essentially compile dossiers on all the good and bad things people have ever done — all of it free and available online, if you know where to look for it. I’m good at it because this kind of stuff fascinated me. This makes me very cautious of people I associate with, but I still do manage to go on a couple of dates when I find the time.

However, after I explain to a girl on the first date what I do, there’s about an 80% chance she’ll ask “so, did you look me up?” I don’t want to say “yes, I know about your speeding ticket, made sure you didn’t have a drug habit in college, looked over your friends, pulled your voter registration, made sure you weren’t a hardcore activist or ideologue who might try and steal my laptop if you spend the night, etc.” (that last one has happened to a friend of mine in the same field, these aren’t paranoid suspicions, just necessary cautions). However, I also don’t want to lie and say “of course not” because a) I wouldn’t want to lie to someone who may turn out to be the real thing, and b) it wouldn’t even sound true. Any ideas on how to thread the needle?

I can’t help but wonder if the woman who tried to steal your colleague’s laptop did so because he went through the “necessary caution” of doing an in-depth background check on her.

We’ve all got dirt, Alex. Run-ins with the law, unsavory behavior at casinos, drugs we shouldn’t have done, people we shouldn’t have fucked, things we shouldn’t have said. What allows the average person to have a romantic relationship with another average person is that most people only judge their partner on their actions since they met that person. Granted, I don’t want to date someone who’s cheated on every boyfriend she’s ever had, but I also don’t give a shit if someone had a drug habit in college. THAT’S WHAT COLLEGE IS FOR, YOU ASS. I mean, you’re judging people based on paperwork filed by government employees. Have you ever met a cop? My friend got ticketed for an open container violation last month as he was walking to throw away an empty bottle.

What I’m trying to say is, relationships are about trusting someone. When you do an in-depth background search on someone — not just a standard “Is this person a murderer?” Google search — you violate that trust before it even has a chance to form, and you’ve already formed opinions about someone who very likely has changed and grown and matured since they did whatever you dug up on them.

My recommendation, obviously, is to not do the background search on women you might like. Instead, turn it from something creepy into something intriguing. When your date says, “So, did you look me up?,” you say, “No, I like to form my own opinions about people I’m interested in.” And THEN you hit her with this: “Why? What would I find out about you?” See, that shows that you want to learn about her from her. If the date goes really well, you can invite her back to your place — “I’ll show you how to do a background check” — and you can dig up the dirt on her as she watches. She gets to see how you do your job, she can explain why she attended a communist rally when she was 19, and you get verification that she doesn’t have AIDS before you sleep with her. High five!

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