Hi friends. I’m still plowing through the backlog of emails from a couple weeks back, but keep sending us emails — I’m reading the new ones and trying my best to perform triage on the collection. Keep ‘em coming. (“That’s what she–” *beaten into submission with reeds*)

ANYWAY: this week we’ve got the titular booty texts and gifts of hookers, plus a couple emails from lady readers, Kaepernick versus Luck, some folks with questions about serious-serious relationships, Scarlett Johansson, and more. MORE THAN SCARLETT JOHANSSON, you ask? Yes. Read on.

Dear Captain Caveman,
Fantasy: None.Had to give it up two years ago, because it was practically dominating my life. But I did win my league last time I played, which was very satisfying. And I couldn’t have done it without your help,

That’s very nice of you to say, liar.

so thank you for what you do. Keep up the good work. Here’s a picture of Scarlett Johansson that I know you’ll enjoy:

Sexy Times: My relationship of about eight-months ended recently. I’m 27 years old and I’ve always had issues sustaining relationships past 6-8 months. And I’m trying to figure out exactly what’s going on. Maybe there is something wrong with the way I approach relationships or somehow I end up with the wrong girl every time.

EVERY person’s the wrong person until you find someone who agrees to be with you until you die.

My question is this: what sort of clues or signs should I look for early on to gauge if I’m in a right relationship or not? I’m a fun, loving guy, with great sense of humor and with moderately successful career. My last girlfriend (23 years old) said we had a lot of fun together but that she just wasn’t into it anymore. I’m going to be moving to a different city for work, and maybe this had something to do with it, but I know it wasn’t the deciding factor in our breakup. I’m just getting tired of going through relationships after relationships, and have nothing major to show for. What do you think?
Thanks for your input,
Sexy Rexy

Think about it: what benefits are there to being in a long-term relationship that ultimately doesn’t work out? Aside from the obvious accrual of life experience and learning how to be a caring, communicative partner — which I admit is important — a failed relationship is ultimately wasted time. Wasted time that provided you (ideally) with steady sex and good memories, but still: wasted time. And the longer one person in a relationship knows it’s not going anywhere but doesn’t say anything, the more time each person is wasting.

Six to eight months is a great time period for a relationship — long enough to learn what the other likes sexually, long enough to fall in love, long enough to decide if it can grow into something serious. But it’s also short enough to NOT be a substantial chunk of your life, which is important if you happen to realize you’re dating a lying sociopath. Plus, if one person wants out after a couple months, well, at least nobody spent six years waiting for an engagement ring the other person had no intention of buying.

Before I met my wife a little over three years ago, my standard threshold for a relationship was 8-12 months — I’d only been in one relationship for more than a year (a disaster that should have never lasted beyond the third month). Shorter relationships didn’t make me unprepared for marriage; they helped me hone in on what I wanted from a relationship. And when I finally met my wife, I was like, “Aw dammit, she’s awesome. If I start dating her, I’m never going to date anyone else.” And I was right — except for the part where I was bummed about not dating any more. That feeling, or something similar, is what you should be looking for — a sense of “being with this person is better than even the possibility of being with someone else.”

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Dear KSK,
Fantasy: Due to random luck, I have the option of keeping either Andrew Luck or Kap’n Kaepernick in my big dollar league (4pt passing TD’s, no draft penalty, can keep either a max of 3 years). Obviously it’s April so who the hell knows, but I can’t decide if Luck will explode in his second season, or if Kaep has the higher ceiling with rushing yards and TD’s.

Eep. That’s a tough one. A couple considerations:

  • Luck is a pretty good runner himself — 4.1 yards per rush in his rookie season with five touchdowns, as many as Kap (though obviously Kap had fewer starts, and a better YPC of 6.6)
  • Luck only had a 76.5 passer rating thanks to a 54% completion percentage and the 23-18 TD/INT ratio. But part of this is because he was asked to a throw a ton because the Colts defense sucked and gave up a ton of points. Kaepernick, with better assets all around him, had a 98.3 rating.
  • The AFC South is not nearly as competitive as the NFC West.

I think Kaepernick is an amazing player, but I’d probably go with Luck for three reasons: I expect him to continue to improve, the lighter competition, and what I perceive to be a lower injury risk. (I also think Luck will have less variance in his performances.)

Sex-bag: Here’s a question that’s been bouncing around my group of friends for some time. At what age is it appropriate to hook up a buddy with an escort to take his V-card? Is it appropriate in the first place?

It seems weird from the get-go. As much as I want my friends to get laid, I would never buy them an hour with a hooker. Unless there was a really good Groupon.

That said, if someone had done that for me, I wouldn’t have objected — but I’m also an amoral monster. It really depends on the individual’s opinion of prostitution.

A little back story, we’ve had a good friend since high school, we’ll call him Neckbeard of Fate,

#NoF

who’s been trying to date above his grade for as long as we’ve known him. Socially he’s always tried to go his own way; completely oblivious that awkward confidence and obscure geeky knowledge isn’t a panty dropper. NoF also has not taken a cue from a decade of rejection, and is a virgin at 30 despite his best efforts.

We debated getting him an escort when we were in Vegas several years ago. NoF wasn’t really for or against it, but I was of the opinion that paid sex is a shitty way to pop the male cherry, and it could be tough to explain to the future mythological woman that is actually into him.

Is there NOT a shitty way for a guy to lose his virginity? Even if it’s in a hotel room on prom night with the head cheerleader, it’s still going to involve awkward fumbling and be over too quickly. (Also, I don’t think your 30-year-old friend should be going to a high school prom.)

If anything, I’d think that a decent sex professional would be able to guide him through the experience without making him feel self-conscious. She might even prefer clients with quicker triggers (I’m guessing here, as I don’t have any actual experience having sex with hookers).

As for this mythological woman who decides to date your friend Comic Book Guy, why would he need to explain how he lost his virginity? Couldn’t he just say “it happened way too late in life, and it wasn’t with anyone special”? He could just say it was a one-night stand, and it would be a perfectly true presentation of the story.

Several years later, he’s on his own in a midwest city and still can’t get any action, and I no longer trust my convictions. Do we let Neckbeard of Fate do it on his own, or do we go for the assist?
-Awkward Confidence.

It’s not anything that I’d do for a friend, but I’m also not friends with people who grow neckbeards. I hate to use a fish metaphor here, but: “Give a man a fish, he’ll eat for a day. Teach a man to fish, he’ll eat for a lifetime.” I’ll pause while you all make super-obvious jokes.

You’re seriously considering buying the guy a hooker, but have you or your friends ever told NoF to shave or offered tips on approaching women? That would be a truer mark of friendship, in my opinion.

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LADY EMAILER!

Dear KSK,
Fantasy: What are the best guides for joining/picking a fantasy team? My guy friends are always asking me to join their leagues because I’m huge college football fan. And we can debate all day about college football versus NFL (mainly that the NCAA exploits players—which it totally does) but I find college football so much more exciting.

Anyway, I’m coming around to the NFL and curious where I should start my research.

You don’t need one, unless you love the feel of paper in your hands. Read the NFL posts on Yahoo’s Roto Arcade, study up on your prospective league’s scoring system, and make a list of the top 150 or so players for your draft. It doesn’t need to be an obsession (until it is).

Sex: I’ve always had long term relationships, but I dated a guy briefly (let’s call him Fly). He was cute, but more so a good hook-up. I got out of a relationship a few months ago (spare you details) and I don’t want anything serious, but I do want good sex and I know that Fly can provide and that he’s single. We’ve texted a bit, but I don’t know how to just say that I’m DTF, even that term makes me feel bad, but it is true.
How do I do this? What do I text?
-Ain’tNoManning

My recommended text: “Hey, what’s been going on? Been too long — let’s get a drink and catch up.” Or if you want to send more obvious WOULD YOU LIKE TO GET LAID vibes, the magic phrase is “been thinking about you,” which 100% of the time translates to “let’s fuck, and soon.”

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CONSECUTIVE LADY EMAILERS!

Dear KSK,
Fantasy: Mine? To own an island! I’m at work, or else I’d send you some risque photo… Sorry!

While you probably meant that you’d send a risqué photo from an internet search, I do appreciate you phrasing it in such a manner that it sounds like you’d send a risqué photo of yourself if only it weren’t for your peeping co-workers. Fortunately, this isn’t The Chive.

Sex: Sorry again, it’s not even about sex. I’ll be short and sweet. How important/unimportant is it for the families (nuclear) of a couple to get along? I’m dating a great guy and have been for a couple of years now, but I worry about the differences in our families (his family doesn’t drink– religious reasons — and mine does etc. etc.). We aren’t yet talking about marriage, but I worry about the ramifications of two families that don’t care for each other? Does this even matter? Am I an insane person?

Thanks!
-Donna

Anyone who tells you it doesn’t matter is either an orphan or an ignoramus. It absolutely matters. You never marry just a person — you get their whole family bolted on to your life. But that’s not to say it makes a relationship impossible — I know LOTS of people in happy marriages that have shitty in-law situations. It just means the wedding might have some awkward moments, and you’ll have a couple more family-related headaches on an annual basis. For me, “bad prospective in-laws” falls into the same category as “long-distance relationship” or “dating a co-worker.” It’s never a recommended course, but you can navigate it well enough with love and patience.

For everyone else: marry people whose parents are either dead or still married.

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Captain,
Fantasy Futbol: I’m 2 points out of first place with 6 games to go… Robin Van Persie has been my work-horse for the entire season, but he’s old and hasn’t been scoring like he was earlier in the year. With Gareth Bale injured, should I just throw caution to the wind and pick up Gervinho? I feel like Arsenal will still have a ton to play for chasing that last Champion’s League spot, while United already have the league wrapped up. That being said, it’s fucking Gervinho! Ugh, so many mixed feelings… Thoughts?

Sex: And now to the waffling pansy portion of the email: I’m a 31 year old who has been dating a 26 year old for almost 2 years, we’ve moved in together back in October and things have been going great… She’s a 6’1″ former model who is smart, hilarious, really just brightens up a room, gets along with all of my friends/family, has an awesome and lucrative job in tv, and I can’t imagine waking up next to anyone else. It’s gotten to the point where marriage has become a common discussion and while my first reaction is that it’s definitely something I want to do, I still just have my lingering doubts. Here’s the thing, she’s pretty much my first serious love, and I’ve been conditioned by an entire lifetime of shitty jewerly commercials and romantic comedies to expect some Disney Prince, hearts-shooting-out-of-my-eyes-when-I-look-at-her-bullshit, and I just don’t have that.

You: “I can’t imagine waking up next to anyone else.” Not sure what else you’re looking for.

That being said, I’ve done the whole sex with random strangers thing for the better part of a decade, and while I really enjoyed that part of my life, I definitely like this more. I just ALREADY feel like I’m part of an old, married couple, and as I have absolutely no past experience here, I’m wondering if this is a common occurrence. Don’t get me wrong, I love it, but I just have assumed my entire life that everyone who gets married has the ol’ stars-in-the-eyes, and Christ, 50% of those relationships don’t work out. Thoughts/experiences from married/divorced people both young and old would be greatly appreciated… Fuckin’ pragmatism, thanks for that, dad.
Xoxo,
Peter Peter Blumpkin Eater

Well, you can’t be THAT pragmatic if you’re expecting more than you already have: a successful, sexy, funny person who all your friends and family ALSO love (your friends and family, if they’re reliable and supportive, are an excellent barometer).

Let me ask you this: what, exactly, is wrong with feeling like you’re part of an old, married couple? Staying in and enjoying each other’s company instead of going out and being exhausted the next day? Finishing each other’s sentences? Feeling comfortable and content? That’s all a big chunk of my married life, and I think it’s pretty great.

A couple times before I got married, I had that Disney version of love you talked about: nervous stomach, heart thumping, bad poetry, woodland animals hanging out on my shoulders. I don’t deny that that was love, but it also wasn’t a strong enough foundation to make a lasting relationship. I’m not saying that my relationship with my wife is by any measure dull or unsexy, but it’s not innocent. It’s mature, and as a result, the love is a bit more measured. A steady burn rather than a wildfire, if you will. And I like that — it’s better suited for a long life together.