What’s the Best Holiday for Sex? The KSK Sex & Fantasy Mailbag

11.27.13 4 years ago 74 Comments



Happy Thanksgiving, friends of KSK! After last week’s trickle of letters, you all stepped up with a flood of emails that I couldn’t possibly keep up with. I apologize to those that went unanswered, but I hope our discussion of sexy holidays is enough to distract you from family commitments for a little while.

Have a great holiday, and if you’re traveling, please be safe. On to your questions!

Hey Captain,
Fantasy first. I’m in a 12-team PPR league with only 4 playoff spots, and I’m currently in 5th. I pretty much need to win out to make the playoffs, and the waiver wire is barren. I need to decide between two of these three for my RB and flex spots: Ben Tate (vs NE), Ray Rice (vs Pit) and Coby Fleener (vs Ten). My 1st RB and TE are solid (Jamaal Charles and Gronk). Who should start?

Fleener is an easy choice for your flex — he’s been a reliable option since Reggie Wayne went down. At running back, I absolutely LOATHE Ray Rice this season — and he’s not even on any of my teams. I’m inclined to say Tate, even with Dennis Johnson producing well in the time-share last week.

Sexy time: After a recent hook up with a friend with benefits (redhead, perky tits, 4’11”; I’m not particular about how tall the girl needs to be, but she’s definitely at the threshold of “would be mistaken for child rape if anyone walked in”),

That’s juuuuuust on the far side of “more information than I want”

we started talking about if we should have sex over the Thanksgiving holiday, and quickly agreed that Thanksgiving is the WORST holiday to have sex on. It must be, right? After gorging yourself on enough food to last a week? But then what’s the best holiday for sex? She thinks that it’s either New Year’s or St. Patrick’s, because those are the easiest holidays to get it (they’re the rare days where it’s socially acceptable to be drunk and make out with a stranger, and it’s easy as pie to escalate from there). I contend that it has to be either Christmas or Halloween, just because of the huge range of kinky sexual possibilities. Settle the debate for us, oh captain.
-Minnesota Fats

Unfortunately, the “best holiday for sex” is a little vague, mostly because it’s completely different for single people versus people in relationships. (I ran this past my wife, who said, “Totally true. I really wanna fuck you on Veterans Day, and I don’t think that’s a common thing.” She’s candid.) For single people, the “best” holiday for sex is the one that offers the best chance to HAVE sex. For those who are married or dating, the best holiday for sex is the one where the regular sex has the best chance to become more erotic than the usual Tuesday night missionary session.

So, in my rankings, I’ve done my best to weigh both sides here: single folks looking to score, and partners taking it to the next level.


1. New Year’s Eve. Women wear cocktail dresses, guys dress up, everyone drinks champagne, and the nostalgia for the year gone by combined with the feeling of a fresh start makes everyone more willing to get naked. The social custom of kissing someone at midnight opens a door for single people, while getting dressed up spices things up for couples. New Year’s gets the edge over Halloween on combined appeal.

2. Halloween. It’s not merely that women are in sexy costumes; it’s that the costumes give women alter egos who have more sexual freedom. Halloween is easily the number one sex holiday for singles; it only falls to #2 because I’m not sure that appeal carries over people in relationships.

3. Valentine’s Day. Blech. Not my cup of tea, but a lot of couples dig it, and the cultural focus on couples provides a social lubricant to singles who are out in bars.

4. St. Patrick’s Day. A city-wide bar crawl of drunk people. You HAVE to be single to be excited about your sexual prospects on St. Paddy’s.

5. Fourth of July. Hot weather, social gatherings (rooftop parties, pool parties, beach houses), and fireworks.

T-6. Memorial Day/Labor Day. A cursory nod to the holidays that bookend summer, and the accompanying weekend getaways for couples. Rental house sex is trumped only by hotel sex.

I’m not sure how or where Christmas fits on this list. I think there’s enough cultural influence and sentiment to make the Christmas season good for a little bit of kink — particularly if you go to holiday parties populated by single women in tight sweaters. But Christmas Day? Everyone’s with their families. Single people are at their parents’ houses. Married people with kids are focused on their kids. And in my family, the Christmas meal is almost as gluttonous as the Thanksgiving feast. The only people fucking on Christmas are characters in Love, Actually.


Dear Captain of the good ship Mailbag,
First Fantasy: I’m in a fairly standard PPR 10 team league. Due to Muscle Hamsters stunningly disappointing season, my RB situation is a bit on the shit side. I started the year 5-1, but have since fallen to 6-5 and am on the brink of missing the playoffs. Essentially, I have to choose between Woodhead and Le’Veon Bell for my RB2 spot behind Demarco Murray. Bell has been incredibly consistent at putting up double digit scores, but will probably never have a true big game. Woodhead has been very boom or bust, but due to the PPR nature of the league he has been incredibly useful throughout the year. Normally, I’d go consistency with Bell, but the potential for Woodhead is making it very difficult. Help?

You think Woodhead’s boom or bust? With PPR, he’s registered 10+ points in 9 of 11 games. He’s a must-start in leagues like yours.

Now for the sexy: I am in an amazing relationship with an amazing woman, and incredibly happy about it. So happy, in fact, that we are getting married next summer. Now, I have no complaints about her or our relationship (we are very kinky), and I certainly find her sexy enough on her own. That said, as a man, one of the things I’ve never done but always fantasized about is a threesome.

Obvious sentence is obvious.

She has expressed interest in the past about potentially doing one, but I always got the vibe that it was just her trying to appease me with the possibility. I never wanted to put her in the position of doing something that she wasn’t totally comfortable with, and she is definitely on the protective side when it comes to other girls and myself. I just assumed it would remain a fun pipe dream.

However, last weekend we went to a strip club together with a group of her girl friends. We ended up getting a private room together and her and the stripper began having a good deal of fun, much to my delight. I assumed her actions the night before were mostly the result of alcohol, but while laying in bed the next morning she quite casually remarked “I think we should really have a threesome.” Naturally, I quite agreed. I have never had qualms about myself in a threesome with her, she is the love of my life and I want absolutely no one but her in a relationship.

I have two real questions regarding going through with this: First, any suggestions at all about ground rules or otherwise good things to look out for when actually doing it? Second, and more importantly, how do we actually go about making it happen? I haven’t been single for awhile, and even then it seems weird to use the same tactics to try and pick up girls with my fiancee by my side. I would like to avoid going the creepy craigslist route, but I legitimately don’t know where to begin. Any help would be appreciated.
Hingle McCringleberry

You should absolutely have some ground rules — specifically, your fiancee needs to say what she’s NOT comfortable with, because I’m guessing you’re going to be cool with just about anything. I would also recommend a code word or phrase that she can say if she’s uncomfortable with something or feels jealous about the attention your third is getting. (It can even be something simple and straightforward as “my turn.”) You don’t want to choreograph the thing, but you need to understand each other’s expectations, and agree on what’s okay and what’s not.

As for finding that third person, it really hinges on what your fiancee is comfortable with. Some ladies will lean towards a longtime friend that they’ve always found attractive; others may prefer a stranger. She may not want your threesome friend at your wedding, you know?

The single best thing you can do, honestly, is let your lady drive this bus. You’re a dude asking a dude about a sexual experience that mostly involves women. You’re much better off tuning in to the female experience. Here’s what one experienced lady has to say about FFM threesomes:

The girls, pretty much under every imaginable circumstance, have to get on as friends at LEAST and it’s preferable if they want to jump each other’s bones regardless of the guy being in the room or not. I will be honest- I have not heard of a threesome involving a couple where the guy picked the girl, the two girls focused on the guy, and this didn’t end in pain and tears. It is drama city, believe me. It works out much better if the two girls go at it and the boy sits on the sidelines some of the time. That scenario where the guy and girl fuck and girl #2 just sits aside and makes o faces while she masturbates? I’m sure it’s happened outside of porn, but I don’t recommend it unless you’ve specifically negotiated that scenario and/or hired the other girl.

As a girl joining a couple, this is fun and fine if you’re ok with the lack of responsibility and emotion that comes from being a living sex toy… which is usually your function. In fact, I would say have “living sex toy” as your base expectation. Don’t get me wrong, I’m not dissing that at all- in fact that’s what I loved about threesomes for a long time!- but if you expect to be treated as a lover you might feel disappointed, depending on what the negotiations indicated.

Also? Meet the girl from the couple individually for coffee or a pint first and double check what she likes, flirt with her more, play with her more. Her happiness = your pleasure = less headaches all around.

I also recommend this lengthy guide to FFM threesomes — again, courtesy of a woman with the experience — which addresses your question about finding a third better than I can. Good luck, and happy fucking.


Football first: I have no good excuse, but this year I am simply horrible at fantasy football. Despite usually being quite competitive, my picks simply didn’t work out this year. Any recommendations for helping to enjoy the last few weeks of the season? I’m a Dolphins fan, so that’s no option.

That’s a tough one. I’m in one league where I’m unlikely to make the playoffs — I’m at 5-7, and one of seven teams that’s either 6-6 or 5-7 (it’s like the AFC) — and so I try to find smaller consolations: spoiling others’ playoff hopes, working towards my aggregate point total (it’s usually higher than my W-L record, because life’s not fair), snatching players off waivers before other teams… That may sound small and boring, but it’s not: I’m playing for pride. As a great coach (Pete Carroll) repeatedly tells his team: ALWAYS COMPETE.

Sexy Sex: There’s a girl I’m interested in and we’ve started to flirt a bit. The thing is, I’m moving away in a few months and wonder if I should start anything serious with the spectre of distance coming in so quickly. Is it worth it to throw caution to the wind, or should I realize it’s only a fun little fantasy that is incredibly unlikely to lead anywhere?
-Wistful in Williamsburg

Definitely DON’T make a move. That way you can move away and always regret not doing anything and wonder what might have happened.

(Go for it, dummy.)


No fantasy… Just sex. Or, not sex, or for that matter, intimacy

I’m 21 yrs old. I haven’t had sex since I was nineteen, a funny story, by the way, that involves me not knowing where I am. Honestly, I have “general region of a state” and that’s it. 


Frankly, I’m impressed. You have a much better “losing your virginity” story than anyone I know.

I really haven’t had a ‘prospect’ since then either. I know the Captain Caveman rules for getting on the market again. What about getting on the market at all? To be honest and with a lot of embarrassment, I have a lot of anxiety, and I have a hard time talking to people at all, and all of my close friends are in long-term relationships (I anticipate drinking heavily soon as my buddies fully set themselves apart from Bachelorship).

I’m drunk right now. I taste her lip gloss on my lips.

Oh man, this is gonna get sad, isn’t it?

I made out with a girl dancing tonight, and afterwards, after some other fellow gyrated his hips into her, I went up to her and apologized for kissing her. For some reason, Big Daddy Drew comes to mind: “The terrible part about being lonely isn’t the isolation It’s the feeling, deep down in your guts, that you will ALWAYS be isolated, and that you deserve it.”.

This may have been a bit discombobulated. It probably is. Fully aware of how pretentious this sounds, it sometimes (most of the time?) feels like I’m destined to be alone.

Wow, this was depressing. But UFFsides is awesome! Seriously.
Any advice? Just in general?
With all regards,

So, okay. Pep talk time.

You quoted Drew, because he captured how you feel right now. That’s your focus: the present. You’re zeroed in on the pain and loneliness of Drew’s quote, so you miss the bigger picture: Drew is happily married and successful, and not at all FOREVER ALONE. He didn’t fit in and felt awkward throughout his teens and college years, but he used that experience to grow as a person, which eventually translated to progressively better jobs and a wife who’s really smart and sweet and good-looking (and they’ve got cute kids, too).

Drew’s voice — both written and in person — is so strong and resonant because he has a crystal clear sense of self. He’s not afraid of anything that you can find out about him, because he’s already shared everything embarrassing and shameful about his life. Nothing in his past is going to change his life as a husband and father.

Now, we all can’t turn out as well-adjusted as Drew, but you should at least recognize that life is long enough for shit to change. Right now, you’re technically an adult, but you don’t have enough life experience as an adult to realize that there are ups and downs. You have YEARS ahead of you to become smarter, stronger, and happier — and it can all be done without a girlfriend.

So, go read everything you can get your hands on. Go see live music whenever you can. Exercise a lot. Travel as much as you can. Push yourself outside your comfort zone. And for God’s sake, never apologize for kissing a woman if she kissed you back.


How’s it going?

It is going well, thank you.

Football: I’m in a 10-team standard scoring league non-PPR, and I need some help figuring out my WR situation to end the season. I’ve got Cruz, Garçon, Amendola, and Denarius Moore (with Streater available in FA). Amendola got my hopes up with his 18 point game a couple weeks ago, but now is only good for jokes about his injuries. Who should I finish out the season with? BONUS: Gonzalez or Delanie Walker at TE?

This week, I like Garçon against the Giants — he hasn’t gotten into the end zone enough, but with at least 5 catches in every game, he’s a reliable play. I also like Cruz — he’s been quiet lately, but the Redskins’ D can cure any ailing offense. Week to week, those are the two I’d favor, but I also think Streater’s a decent play against the Cowboys this week if Moore doesn’t play. (Basically: start players going against NFC East defenses.)

Sex/Relationships: My girlfriend and I are coming close to a year together, although it’s been going on for longer than that in not so serious terms. Recently she started asking me how much I talk to an ex, and I was honest and said we text, but it’s usually about dumb stuff (stories about coworkers from the old company we were at, OMG LOOGIT THIS PUPPY I SAW). My girlfriend calls me a liar, and says she went through my phone

and saw we talk about more than that, and cites other normal conversation topics like how life is going for each other. I should also point out that I moved halfway across the country for my current girlfriend, so it’s not like I’m ever seeing the ex again. How concerned should I be about the snooping?


I tried to let it go, but when I got up this morning and showered, I’m pretty sure my phone was on a different screen than when I got up, so I feel like our trust is pretty weak right now. Little help here?

Short answer: that GIF above.

Long answer: what your girlfriend did was shitty to the point of unforgivable. I’ve dated jealous, distrusting women, and I’ve known a few others. The refrain goes like this: she pokes through your phone or email until she finds something she doesn’t like, then she goes fishing for an argument with her fresh bait. She asks you about X woman in your life — co-worker, ex-girlfriend, female acquaintance — and your response is wrong. No amount of truth you deliver can sate the simple fact that you were communicating with another woman, which she views as her COMPETITION even though you can’t make it any plainer that there IS no competition. Then you point out that, hey, what the fuck was she doing snooping in your phone/email/whatever, and she comes back with WHAT DO YOU HAVE TO HIDE? The entire argument happens on a separate plane of insanity governed by her distrust, and it’s impossible to reframe it in a world of trust.

Straight up: a person’s phone is their personal shit. If the other person in a relationship doesn’t trust what’s in that phone, they shouldn’t be in the relationship. If you want to try to save your relationship with your girlfriend, you need to communicate that to her, and she needs to accept it with no bargaining. She’s 100% in the wrong, and I wouldn’t blame you for popping smoke and getting the fuck out. There are LOTS of people in the world you can love who don’t need to violate your trust to serve their jealousy.

P.S. Finally watched Keepers after you trying to force it on us for weeks; it’s pretty damn good compared to other fantasy segments out there. While I did go with Donald Brown this week, I took comfort in the fact that Indy got crushed for not figuring out their backfield.

Thanks! Here’s this week’s episode:

I also now do a waiver wire edition of Keepers on Tuesdays. You can find those on SB Nation’s YouTube page.


Dear Captain,
Fantasy: I have two questions, one quick start/sit and one etiquette related.

First, in my 12 Team PPR work league I am locked into the #1 seed (despite my first two picks being Doug Martin and Randall Cobb) but there is a payout for the top scoring team for the regular season. I am behind by 12 points right now. PPR scoring so who do I start at flex: Pierre Thomas @SEA, Chris Ivory @MIA, Marques Colston @SEA, Michael Floyd @PHI or Reuben Randle @WAS?

Mmmmm… Reuben Randle.


I like Floyd’s matchup the best — the Eagles give up the most fantasy points to wide receivers. if Darren Sproles doesn’t play, I think P. Thomas is a good play despite the Seahawks’ defense. Randle offers nice upside, but I think Floyd or Thomas are the way to go.

Second, in friends’ money league I am missing the playoffs despite being the top scoring team in the league. I know fantasy football hard luck stories are a dime a dozen but I am writing because of an unfortunate scenario: this past weekend the guy ahead of me won his matchup because his opponent started three players who never took the field (Pryor, Rudolph and Denarius Moore). This opponent clearly didn’t pay attention the previous week either because he played someone on their bye. I don’t want to whine about it too much and seem like a sore loser. I’m accepting the hit but I’m curious as to your recommendations to avoid this sort of thing, short of not inviting the types of jackasses who won’t finish out the season into the league to begin with?

Suck it up. The aggregate points/head-to-head record disparity is the bad beat story of fantasy football: bad luck happens, and talking about it in detail is only going to bore people. You’ve almost certainly won fantasy matchups thanks to people not setting their lineups, but they don’t stick out in your memory because your wins are all due to your PROPHETIC BRILLIANCE, of course.

Relationships: Happily married for three years. Things are going great and my wife has been very understanding and supportive while I finish up graduate school.

The thing you said last week about how not getting yourself into situations where you have to make a decision about cheating is just as important as not cheating rang very true. I agree and have approached my social life in the same way. There is one minor issue of discussion with my wife though. I have no trouble telling female friends when they look nice in a particular outfit or on a particular day. Usually this will take the form of what I consider to be benign compliments, such as “That shirt looks good on you, Prudence.” My wife views this as flirtatious and thinks I am being too forward. I should note that I say the same things to her as often as possible so it’s not like I don’t take every chance to tell her I think she is beautiful.

So where do you stand? Is it ok for a married man to compliment female friends on their attractiveness or is it something I should curtail? I have avoided it since I found out it bothers my wife for her sake but I just wanted to get another opinion on the matter.
Thanks a bunch,
Cal the Flirt

I’m a frequent and unabashed complimenter of women, both at work and among friends. And I’m with you: because I’m married, the compliment means I’m just being nice, not that I’m trying to flirt or pick up some floozy on the side.

Unfortunately, not everyone is going to take it that way, and when you say, “that shirt looks good on you,” it may be a little too close to saying, “I’m really enjoying looking at your tits.”

Here are compliments I like to give. I usually say them with a gay flair to eliminate any chance of a “creepy married guy” feel. Feel free to use them:

  • I like your hair like that!
  • Great shoes!
  • That’s a really cute top! (Women call shirts “tops”)
  • *Someone* got dressed up today!
  • I love your scarf! You’re like a young Stevie Nicks, but not on coke.


Fantasy: I’m barely hanging on for playoff life in my 10-person PPR league (started 1-5 and was bolstered by an RG3/Cameron for Newton/Bennett trade and a Dez for AP trade). I’m now at .500 thanks to those deals, having LeVeon Bell and Gronk in my lineup, and getting better work from Andre Johnson and Hilton. Does your late-season (if you’re still in the hunt) or playoff strategy change for starters? I have Newton/Brady, AP/Bell/Bernard/Spiller, Andre/Hilton/K. Wright/waiver pickup, Gronk/Bennett; I have depth but am not sure to just go with the top producers or play more hunches (like Brady over Newton some weeks).

Depending on my position in the standings and the kind of fantasy matchup I have, I’m a little more open to taking risks later in the season. If my opponent is favored by 25 points and I need a win to get into the playoffs, I’m more inclined to play Kenny Stills or Tavon Austin over Brian Hartline, because I don’t really have a shot unless I get a boom from a boom or bust guy, you know?

(Kind of) Sex: I have 1 philosophical and 1 practical question. Online dating seems to generally be going the same way as other relationships; I’m attracted to women who aren’t to me, and women are attracted to me that I’m lukewarm about. I don’t need you to be my therapist or anything, but do I need to go Costanza on this and just do the opposite of what I want?

This was my experience with online dating in the very narrow window I tried it in 2004, and I stopped doing it for that very reason. I’d send messages to women I was attracted to and never hear back, then get messages from women that I wasn’t particularly attracted to.

And you know why? Because we all think we can do better. And in real life, we often can: charm and wit and wealth or whatever selling point you may have is more readily apparent in person than it is in a photo and an email. I know online dating is more efficient, but meeting people in real life will always be my recommended approach.

Secondarily, one thing with online dates that concerns me is coming off too considerate and polite; all of the women I meet from this site say they get tons of shitty messages, yet they seem to move on when I don’t make a strong play. I’m not afraid to go for it, but am I wrong to assume that most women in an online situation aren’t interested in fooling around a little bit on a first date? Louis CK’s bit about men being the biggest threat to women keeps running through my head when I think of online dating.
-Ozzmatazz Buckshank

You’re wrong to assume anything about “most” women. The only thing you should do is be yourself and say what you feel. Like, if it were me, I wouldn’t be able to stop saying things like, “Listen, I really want to take you out a drink, but don’t assume that means we’re going to have armpit sex. I’m a gentleman.”


Good Sir,
Sex: I wrote to you this past summer asking for your advice on I should approach telling a woman I was dating and that I really liked that I slept with her best friend years ago before I knew they knew each other. I went with the first of the two suggestions you made and without going into details it was labor day weekend when the opportunity presented itself organically as you said it might and I decided to reveal the truth. While it wasn’t an easy discussion, in the end it went as well for me as I could ask for. We’re still together and have a happy, healthy relationship. Doff of the cap to you, Caveman.


Fantasy: In the same mailbag I asked you what RB you liked at the #6 pick where I’d be drafting. You advised McCoy or Spiller, both of whom I also viewed as top-5 RBs behind AP along with Charles and Dougie. At 6, all but Spiller were left so I drafted him and you know the rest.

Hey now! I also said Calvin Johnson would be a good choice there, so don’t put this on me.

Along with losing Wayne, Cobb, and Blackmon for the year he’s been my biggest problem but a 5-0 start means I’m just barely in the playoff hunt and can guarantee entry with a win in the season finale this week.

So with all that said, in a .5 ppr with my playof spot on the line, pick 1 RB, 1WR, and 1 flex from the following- Fjax, Spiller, Mendenhall, Sproles, Torrey Smith, Riley Cooper, Jordan Cameron.

May your thanksgiving be stuffed with food and victory.
– Another satisfied customer

Barf. Cameron has the best matchup and could benefit from Weeden’s return — his numbers really dropped off when Campbell was starting. Torrey Smith and Riley Cooper are both solid plays but have tough matchups. Fred Jackson seems like a smart play at home against the dogshit Falcons, but how do you know if it’s going to be the week that Spiller gets favored?

I think I’d go with Cameron — the Jags give up the second-most fantasy points to tight ends.


Happy Thanksgiving. What’s your preferred cheap bourbon? Old Crow was my weapon of choice in college, but I haven’t had anything on that list since I got a big boy job. Wondering if any of these are actually decent after drinking +/-$30 bourbon lately.

The only two on that list I drink with any regularity are Evan Williams and Benchmark, but only because the liquor store downstairs doesn’t carry Old Crow Reserve. I tend towards the Evan, but mostly because I’m a creature of habit.

Anyway, for fantasy I am tied for the last playoff spot with the guy I am matched up against this week. Two questions, QB and Flex. [6 point pass TD, 0.5 PPR]

For QB I have Cam and Brady. Leaning Brady. I feel good either way.

As you should. A warning on Brady: the Texans have yet to allow a 300-yard passer this year, though Rivers and Luck both had big fantasy days by throwing for 3+ scores, so you should be okay with Touchdown Tom. I’d probably lean Newton at home against Tampa Bay, but like you said: you should feel good with either.

Flex is a little tougher. I have Hilton (vTEN), Colston (@SEA), Ellington (@PHI). I’m trying to get Steve Smith (vTB) off waivers. Indy has been crap lately and Hilton has been kept in check the last two weeks. He probably still has the highest upside of my options, but I’m leaning toward Steve Smith (I really want to yell “ICE UP, SON” at my opponent if I win this week) if I can get him. Burleson and Justin Hunter are also on the wire and I have claims on them in case I don’t get Smith.

Slow your roll on Steve Smith; he hasn’t gotten to 70 yards receiving in a single game all year, and he only has two games where he’s topped 10 fantasy points (well, three games with 0.5 PPR). I wouldn’t count on a huge day on Revis Island.

Go with Ellington. The Philly D is Swiss cheese.

Sexy: My girlfriend hinted she’d like me to buy her some lingerie soon. Kind of a weird question, but anywhere besides Victoria’s secret you recommend? Agent Provocatuer is awesome, but I’m not exactly in that tax bracket.
Talib’s hip

Unfortunately, there’s no such thing as “good cheap lingerie.” If you want a big step up from Vicky’s in quality and a small step down from Agent Provacateur in price, I recommend Journelle. It features several different designers, so there’s a variety of styles to choose from.

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