The final week of the regular season is upon us, which means that for most of us, the fantasy football season is over. God, that’s so depressing. I may drop some money in FanDuel just to get that fantasy rush of endorphins during Week 17.

Anyway, in case you’re interested in my fantasy credentials, both of my teams finished 8-5 this season, good for a 3-seed and a 4-seed. Then Aaron Rodgers got a concussion in Week 14, and I felt the unique pain of having the same player anchor both of your fantasy teams. Now, after three years of playing fantasy football in multiple leagues, I’ve never missed the playoffs — and I’ve never made the championship game. Which means that the advice you get here is guaranteed to be SLIGHTLY ABOVE AVERAGE. All for the low, low price of free. Nice!

But enough about me. Let’s get to the letters.

This first email came in a while ago, but I’m publishing it now because the fantasy question isn’t time-sensitive. And also because this chick seems cool.

Oh Captain my Captain,
Sex first, because that’s why I’m really writing, although I promise to observe the rules of the FF/sex mailbag. About 10 days ago began communicating via email and text with a guy I met online and it quickly became (pre-first-date) sexy (read: smutty texts and IMs), which was great because although I am looking for a long-term relationship and that is clear from my profile, it had been over a year and I could handle a nice uncomplicated romp. We meet, have a great night, with a real connection—flirty but also standard awesome first date stuff sharing tons of common interests and life stories— which culminates in exceptional sex (twice- go me, and hats off to him for his truly amazing recovery time).

THAT’S GOOD HUSTLE! When I’m not in a relationship, I always try to get 2-for-1 deals when I hook up, because you never know if that’ll be your last chance to have sex. Who knows, maybe you’ll have a two-month cold streak and then get hit by a bus, and you’ll lie there dying in the street thinking about how you should have nailed Melinda the morning after that one time you banged her. No thank you.

Anyway, that’s why you should always carry two condoms (also handy if the first one breaks).

Now, I am certainly smitten but getting the vibe that he may already be pulling back (mostly related to him not making firm plans to see me again, although he does have an intense workweek and we are still exchanging sexy messages daily). So, my question is actually NOT a specific one to this situation because hey, what happens, happens, and things are still evolving. No, my question is: why, in general, do games seem essential to finding love?

I respect that you’re not hating the player, but the games instead.

What I mean is, here I am, attractive, educated, successful, with a healthy libido and I connect with a guy who finds me as such and we have lots in common and spectacular sex, but the reality very well could be, I blew it right out of the gates by offering such an open attitude towards and easy access to sex (and dirty sex at that). I know, he and I will probably have the requisite ‘where is this going’ conversation, so again, not about this situation in particular, but why does it seem that a girl has to withhold sex for a certain amount of time, be shy or reticent about it, in order to be perceived as ‘girlfriend material’? Wouldn’t you think it’d be an easy win for the guy: “hey, I meet someone with whom I can talk, whom I find attractive and she can suck the chrome off a tailpipe and enjoy herself doing it….this is the girl for me! I must see her again post-haste”?

Well, if you scroll down to the comments, I’m sure you’ll find any number of heavyset blog-reading football fans who are eager to date you — sight unseen — and offer you their sweaty, unsatisfying love.

As for your more immediate problem, I don’t think there’s an easy fix. Men are told at an early age (by women, mostly) that girls who put out right away are sluts and therefore bad. But the message that young men need to hear is that women who are comfortable with sex should be honored and cherished, while attractive-but-prudish girls should be ostracized and told that they’ll die as old maids.

With the guy in question, there are any number of explanations I can offer up, but I don’t think there’s enough information in your letter to come to a definitive conclusion about him. If I had to take a guess, since he hasn’t made plans but is still sexting (ugh, I hate that word) you, the most likely explanation is that he has a gazillion other dates lined up on the ol’ Internet dating service. Especially in big cities, Internet daters can get AROUND. But don’t YOU change what you do just because one guy may or may not have gotten gun-shy. If you feel like the person and the time is right, go right ahead and fuck your brains out regardless of which date it is. You never know when you’re gonna get hit by a bus.

Now for FF, I started reading your stuff about a month ago for the sex, since football is a passing indulgence (my heart is fully absorbed with my Red Sox – yes ridicule away, but it’s lifelong, and I suffered through a childhood of being a Sox fan in NJ, watching whenever they managed to be on the abominable WPIX- gah, Phil Rizzuto!!). And in enjoying your wonderful advice about sex, I also learned enough about FF to think I’d really enjoy it. So my question is: clearly I have missed this season, but when does it start gearing up again, and as someone who works from home (no office) and is in a new city, how do I find a good league which will put up with a chick who knows nothing at the outset (but promises to learn)?
-Mrs. Michael Bluth

Ouch. No co-workers, AND you’re a female tyro? That’s a tough one. The fantasy football season starts gearing up a little before training camp (or the day of the draft, depending on your obsession), so I’d recommend putting it out on Facebook in June or early July that you’re looking for a league. The Internet is incredibly good at finding people who can fill your needs. Like that dude you banged.

**********

Dear Caveman,
I’m new at this so give me a pass and a bit of your wisdom. There’s this angel at my college named Brielle. People say she looks like Vanessa Hudgens if you are familiar with her.

Are you kidding? I work on the Internet. I saw the leaked photos of Hudgens nude, like, 30 seconds after it happened. Familiar with Vanessa Hudgens. Psssh.

She’s the type of girl you don’t mind cuddling with. Girlfriend material.

Or she would be, if you weren’t gay.

We met a few years ago when she dormed with a close female friend of mine and have remained casual friends. We would probably be closer if it weren’t for one small detail. She’s been dating the same guy for 6 years!

I respectfully kept my distance, figuring she was just going to be my crush forever. But around everyone else I made no secret of my obsession for her. It was a running joke between my friends and I. I’m pretty sure it got back to her but I didn’t care because I had nothing to lose. She and her boyfriend were going to get married and I was going to be that one dude who never got a chance.

But this fall it got interesting. To my surprise she got a little flirty. Then a few days ago the unthinkable happened.

She died?

Mid-conversation she broke out the big news. She and her boyfriend are officially done! With one semester of wonderful undergraduate freedom left ahead of me, the girl of my dreams is single and I have a legitimate shot at being her second boyfriend ever.

Ooohh, you can be the Jimmy Johnson of boyfriends! And with that title come all the trappings of dating someone who’s dumb enough to date the same asshole for half of high school and almost all of college.

Now we’ve only hung out one-on-one a couple of times and we aren’t extremely close just yet, but I can’t let this girl get away! With the holidays in full swing and a lot of stressful shit in my future (grad school interviews), it’s the perfect time to have a girlfriend. With winter break just starting I don’t want our relationship to get cold. I really want this thing to progress so I have something to look forward to when I go back to school.

Should I try and be smooth like Kieth Stone and tell this girl how I feel about her? Or should I give her some time to be single and hope she comes to me? I’ve played the waiting game before and lost, which is why I’m leaning towards laying it all on the line right now. I mean assuming I get into grad school my responsibility-free life essentially ends in less than a year. What should be my next move?
-Ho-Ho-Hopeless Romantic

Ugh, the sunny optimism of youth is nauseating.

Your letter inspired a lot of knee-jerk asshole responses from me. I’ve done my best to tone them down in the editing process, but let’s go to the bullets:

  • Assuming you go to grad school, your responsibility-free life will continue for another 2-3 years. Unless you’re working full-time on the side, grad school is only slightly more work than college.
  • Keith Stone? REALLY? Your benchmark for a man being smooth is a fucking Keystone marketing tool? Punch yourself in the dick and go watch Out of Sight immediately.
  • Go ahead and ask this girl out, but for God’s sake, don’t be the anxious little lovestruck dipshit you sound like in your letter. The odds are pretty good that this girl has never taken you seriously as a love interest, and even if you DO successfully win her over and bed her, she’ll have a tough time living up to the ideal of her that you’ve created in your head. She is, after all, someone who spent three years of college dating her high school boyfriend. You know who does that? FUCKING MORONS. (On the plus side, it means you may have a chance with her after all.)

Really, what you need to win this girl over is, like, five more years’ experience with other women. Meanwhile, the last thing Brielle needs is another relationship; she’d benefit more from some penile variety than from another serious boyfriend. Put your feelings on the back burner and just try to nail her.

**********

Captain Falcon,
Sex: How long is too long when considering the time elapsed between a hook up and an attempt to hang out? Like, let’s say I had drunken sex with a girl about a half a year ago, but was never able to secure a second go-round, though (mostly) through lack of trying. How would I look to a girl if I — rather out of the blue — hit her up with a text message or through facebook chat? Is this desperate, or something worth trying? I’d rather not come off as a total creep.

I think you’ve allowed too much time to go by to send a text. Go with the Facebook message (not chat), and be sure to apologize for not following up after the last time. Apologies are powerful things. Saying something like, “I’m sorry I never followed up with you. I really should have, because I had a great time with you. Looking back, I don’t know why I didn’t do that. It was stupid” will go a long way to getting you back into her good graces.

Football: My fantasy football team finished in tenth place (out of twelve), and I’m a Browns fan. Everybody can go to hell.
Cheers,
Petey

Hey, the Browns had a better season than the Bengals. That’s something. In the way that a frozen dog turd is something.

**********

Dear Captain of Carnal Knowledge,
Sex: Fiance and I have been together for three years and will get married in June. I feel like we have the sex life of a couple that’s been married for 20 years with two kids and two stressful jobs. Once a week at most, with the occasional midweek handjob to keep me from complaining too much. Her dirty talk consists of, “Don’t come in me. I haven’t take my birth control.”

ROWR!

I’ve tried everything. Romancing with flowers, cooking, more flowers, massages, throwing her over the kitchen counter, acting like a disinterested macho asshole, etc. The sex used to be wild, but after three years and a troubled history, it’s a flashing red light going off six months before our wedding. Before we were engaged, the problem was that I wasn’t committed enough. Then I busted my ass on two jobs to pay for the ring, and she said I was avoiding her. Now the excuse for our lack of intimacy is that I’m not excited about the wedding.

She sounds like a delight. I’m sure your friends love her, too.

She’s also upset that our plans to buy a house didn’t work because I’m 26 years old and can’t afford one yet. She won’t flat-out refuse sex, but she never, ever initiates and does nothing suggestive. What makes this even more difficult is that she used to be a bona fide freak, and is still sexy as hell (she thinks garter belts are practical).

/enters first check mark under “PROS” list

I don’t expect road-head and public-bathroom sex every month, but I’d like my fiance to want me.

It’s fiancée, with two E’s. Unless you’re getting married to a dude.

So, Caveman, what gives? This has been going on for over a year now. Being a man, I use sex as a relationship barometer, and it’s not a good sign when I’m jealous of Rex Ryan’s sex life. Am I hoping for too much out of my future wife, or is this a sign of even more un-sexy times to come?

What gives? What gives is that you already know that you want to call the wedding off before you enter into a binding legal contract, and you’re looking for validation here in the mailbag. I’d guess you’ll probably find that in the comments section.

If you do actually love this girl and want to marry her — and that’s not the impression I get from your email — then you need to sit down and have a serious discussion about your feelings and needs, and how she isn’t meeting them. But it seems to me like you should do everyone a favor and call the wedding off while you can still get the deposit for the reception back.

**********

Hi there.
Fantasy: Keeper question! Can keep two, I’m stuck between Aaron Rodgers, Jamaal Charles and Calvin Johnson. Could also keep Steven Jackson, Rashard Mendenhall, Andre Johnson or Marques Colston, but I’m not as keen on those four. If it makes a difference, the league tends to overvalue QBs. And no, that goddamn team didn’t win anything.

Wow, that’s a tough one. If your league overvalues QBs, it seems wise to hold on to the best fantasy quarterback in the NFL — at least when he’s not leaving with a concussion after getting you two points in the first week of your fantasy playoffs, the fucking no-good son of a bitch. And as terrific as Megatron is, I’d probably keep Jamaal Charles, who’s positioned to have an even better year next year.

Uhh, other: Think I found my ideal girl. Similar interests, attractive enough and I know she’s into me. Problem: I’m 22, she’s 16 and I’m a coach of hers. Since this isn’t something I wanna go telling people, I really just need someone to tell me I’m insane and should probably turn off my 2-year countdown clock. Oh, and both her parents are lawyers. Yeah, I’m really this retarded. I should save him some time and go find Chris Hansen myself.
Thanks guys,
-Jimmy

You’re not insane. Sixteen-year-old girls can be crazy hot. They also have to be that hot, because they’re some of the dumbest and most annoying creatures on the planet.

Just wait until she’s 18, at which point you’ll be annoyed that she has another three years until she’s 21, at which point she’ll be having more fun with her college friends than her high school gym teacher. Until then, masturbate before work.