I could easily introduce this mailbag with a rant against Valentine’s Day, but it’s been done countless times before in increasingly boring ways: invented by Hallmark, fake holiday, Steak and a Blowjob Day, St. Valentine doesn’t even have a romantic backstory, et cetera et cetera. So I’m against it, but that’s because I’m a romantic S.O.B. 365 days a year. Why should I have to step up my game and buy a gift just because other dudes are thoughtless slackers?

Anyway, on to your letters. As always, my apologies to those that didn’t make the cut.

Captain:
Sex: I’m a senior in college and there is this girl that I’ve had a long convoluted friendship with that has always bordered on becoming a relationship except because of various miscommunications, false starts, and incompatible schedules it hasn’t, almost to the point of absurdity. So I meet up with her at a bar on Saturday night (first time I’ve seen her all semester) and we end up back at her place in her bed making out. She strongly insinuates that she wants me to take her out on Valentine’s. While that is the absolute last thing I want to do (for a variety of reasons) I felt like my hand was forced so I said yes. So heres the question: Obviously I’m going to take her out to dinner, and hopefully fuck her later on that night, but aside from that I have absolutely no idea what to do. Should I get her flowers? A gift? I mean I’m not even officially in a relationship with this girl, although I’d very much like to be, I feel like I’m in a grey area. Any ideas, suggestions, etc. would be greatly appreciated. To top things off she interns at an accounting agency and doesn’t know when she’ll get off that night, she usually works pretty late, so it makes making any sort of plans nearly impossible. Maybe the question isn’t what I should do but more how big of a clusterfucking disaster this is this going to be.

Actually, that intern gig saves your ass. Going out to dinner on Valentine’s Day is misery — reservations get booked way in advance, and every goddamn table is two people in love or trying to salvage a a relationship or having way too serious of a date early in a relationship (that’s you).

Here’s what you do: you tell her that because her schedule is variable, you don’t want to take a chance with booking a reservation she might not be able to make. So you’re going to cook for her. Don’t know how to cook? No problem: the bar is insanely low at your age. The culinary skills of most college dudes are limited to microwaving burritos and ordering pizza, so all you have to do is boil some spaghetti and buy a pre-made salad from the store. For the sauce, buy something in a jar and some dried porcini mushrooms. Soak the porcinis in warm water, then add them to the heated sauce. Practice this sentence: “The store-bought sauce is a little less authentic than I’d like, so I added some porcinis.” You admit to inexperience, but you’re aspiring to do better. Add candlelight and a bottle of wine (have a second in reserve just in case), and you’ve got yourself a Valentine’s date. And here’s the best part: you already have her in your apartment. It’s almost too easy.

If you’d also like to get laid BEFORE dinner, send her flowers to the office where she works. Ninety percent of a woman’s enjoyment from getting flowers is other people seeing her get the flowers.

Football: As a Jets fan I rooted like hell against the Steelers. But when the Packers won and were celebrating all I had was this empty feeling knowing how close the Jets got and how that could very well be them but it wasn’t. I can’t imagine what its like to actually get to the big game and lose, must be hell.
Sincerely,
I’m fucked aren’t I?

It certainly is. *grinds teeth*

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Mr. Caveman,
I know you guys are big on brevity, and my girlfriend reads this site anyways, so I’ll keep this brief and relatively detail-free. My girlfriend has been giving me indications that she wants me to propose some time in the near future. We’ve been dating for almost 2 years, so it’s not as if we’re strangers.

However, I have concerns as we’re still in college, and I’m still undecided as to whether or not I want to get my master’s degree, while she’s thinking about things like marriage and where to live after college. I’d rather not worry about this sort of thing until after college, but she wants me to put a ring on it and make things ‘official.’ To be honest, I’m not 100% sold on marrying this person either, although I’m far from opposed.

My girlfriend has told me several times that she views the point of being in a relationship is to work towards being married, and that’s something that I want down the road, but for whatever reason, I don’t feel ready to make the next step, especially not in college.

So, I guess my question is, are my concerns valid, or am I just subconsciously trying to find a way out of my relationship? And if my concerns are valid, what the fuck do I do next?
Thanks in advance,
-Angelo Mancuso

Well, your girlfriend has a point. I agree that the point of a relationship is to find a life partner (save fuck buddies — beautiful, beautiful fuck buddies), which is largely why (a) I’m single and (b) almost none of my relationships have lasted longer than a year. If I know conclusively that I’m not spending the rest of my life with a girlfriend, I try to do us both a favor and move on.

On the other hand, some of my best friends lived with their girlfriends for six or seven years before putting a ring on the lady’s finger. It seems weird to me that they’d take that long to figure things out, but if they’re happy with the slow progression, who the fuck am I to judge?

The key, as always, is active communication. If both people in the relationship are happy to live together without the promise of marriage, then it’s cool. Likewise if both are eager for a trip down the aisle. But when one person is champing at the bit and the other is… looking at grad school as a potential way out, then you’ve got problems. You and your girlfriend may love each other very much, but if you have different goals with different time frames, then someone’s going to end up unhappy. The best thing you can do is make your desires and your intentions known, and if those don’t align with her vision of the future, then you probably need to part ways.

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Dear Kings of PK Weather Report,
Sex – I’m a happy camper here. Girlfriend of two years, healthy sex life, and she’s about to turn into my fiancee (look ma, two e’s!).

Well played, sir.

Fantasy – I take part in a high stakes league that has been going on since the late 80’s/early 90’s, where at least half of the participants are original members. I’ve been a member for 5 seasons, and I’m consistently in contention and active in free agency and trades. It’s a 12-team league, where teams are owned by one or two individuals. 8 of these teams are made of people I work with, so the tone of the smack talk and interactions are pretty professional, but can be witty and biting.

The commissioner of the league has asked me to take over his role. I want to be respectful of the way the league has functioned to this point, but I think there is room for improvement (non-fraction scoring, weekly free agent auctions with an uncapped budget, non-keeper league w/ serpentine draft system, etc.). As a well established league, how much should I flex my power in making modifications? Should I allow for league members to vote on prospective changes, given how many of them are tenured (for lack of a better term)?
Excited to have the mailbag back,
The Commissioning Virgin

The league’s been around twenty years, only five of which you’ve played in the league. Give it a full year before you make any changes.

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Dear Sirs,
Relationship Question: My girlfriend and I have been seriously dating for a year and a half. We have had some problems in the past, but recently things have been going great. Yesterday, however, she decided to break up with me because she was not invited to my brother’s wedding. My brother is getting married in September, and his fiancee wants a smallish wedding (50 people per side). This caused a problem for our family because my mom’s side of the family is large (75+ people) and we are close with most of them. So my brother and mom put together a list of people and a lot of people got cut (including relatives we see every year as well as some of his friends). My girlfriend is one of those people. I tried to get her included and said I would really love to have her there if it was at all possible, but there wasn’t enough room.

When I told my girlfriend this story, she got very upset. She claimed that my response meant that I wasn’t committed to our relationship. If I was committed, I would have put my foot down and argued with my brother and mom until she was allowed to come. I told her that I didn’t want to be selfish and make this day about me when it is my brother’s wedding. She then claimed that I was putting my brother’s feelings above hers. This led to a huge fight where we broke up. I understand that she is upset about being excluded (and being seen as just a date as opposed to a serious girlfriend), but I didn’t think she would completely lose her shit over this. Is she overreacting or should I have tried harder to get her included?

You, sir, greatly underestimated the importance of weddings to women. As much as I see your point of view — “Hey bro, can’t we get my girlfriend an invite? No? All right.” — I have to admit that she’s totally right. If you did give a shit about the relationship you shared with her, you would have been all, “I’ve been dating this woman for 18 months and she’s not invited?!? Fucking Aunt Janine is invited and my future wife isn’t? FUCK YOU!”

But your weak backbone apparently runs in the family. Who the fuck has a wedding where the BROTHER OF THE GROOM isn’t allowed to have a date? Did your dad not have balls to pass down to his sons?

Football: How would you rank these fantasy QBs for next year: Matt Ryan, Joe Flacco, Josh Freeman, Mark Sanchez, Sam Bradford?
-Baffled Ex-Boyfriend

Are you planning to have an underwhelming quarterback? Ugh. Knee-jerk, uninformed decision: Freeman, Flacco, Ryan, Sanchez, Bradford. I put Freeman and Flacco ahead of the others because they run a little bit, but really, you’re going to have a hard time winning your league with any of those guys.

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Dear Gay Mafia:
Fantasy: I have been in a ten team league for the past five years, and I still have not made it to the playoffs. I have never been the worst, but I have always been just short. This year I was in second place with two weeks to go, and finished fifth (fuck you, Phillip Rivers). I have tried every conceivable draft and lineup strategy. Is it possible this is just a bad streak, or am I the worst fantasy player ever?

You’re probably not the worst ever, but I wouldn’t chalk it ALL up to bad luck. Next year, try being a little more active on the waiver wire, and try to anticipate — rather than react to — breakout performances. See if that helps.

Sex: I have not had much success in the relationship department, either. I don’t have a large circle of friends, and so it’s hard for me to meet women.

Stop right there. The only people who are allowed to say “it’s hard to meet women” are inmates and soldiers deployed to Afghanistan. Don’t blame your small circle of friends, blame yourself. There are PLENTY of women out there, waiting for guys to take charge and say hello.

Five months ago, a new girl was hired in our office, and we pretty quickly hit it off as friends, and started going out for happy hour and the like. Finally a month ago I got the balls to tell her that I wanted to be more than just friends. She said she was flattered, but that she didn’t want to get involved with someone she worked with, because in her experience it can get weird/ugly. I pointed out that I was considering a career change, and the she wasn’t happy at work either. She said that if our employment situation would change down the line, then “we’ll see.”

Yeah, you’ll see… that she’ll turn you down more bluntly the second time.

To her credit, she was really cool about it, it wasn’t awkward at all, and we’ve continued being good friends. I still try to hang out with her as much as I can, because I have a great time with her. But it bums me out afterwards because I’m really into this girl, and I want more.

My question: short of quitting my job (which would probably backfire), is there any way I can get her to change her mind?
-Pale Dragon

First of all, don’t date people at work. Second, a job is more important than a girlfriend. Third, you’d potentially put that job at risk by dating someone at work.

Since we haven’t had a mailbag for several weeks, I’ll restate this for the 18,000th time: when you want to fuck a girl and she doesn’t want to fuck you, DON’T BE HER FRIEND. She knows you want to fuck her, and all you do by being her friend is make her feel good by giving her attention. You’re basically wasting your time just to feed her ego. If you start ignoring her, it will hurt her self-esteem — maybe even to the point of being attracted to you.

If all of that sounds completely insane, welcome to the inside of a woman’s head.

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Dear Dick Joke Debutantes,

Fantasy First: This is the second year in a row that I’ve been runner up to a chick in my league. I’m 99% sure she performed fellatio to acquire most of her team. That’s not why I’m writing. I respect that. That’s good hustle. I don’t even care that she talks a lot of shit (comes with the fantasy territory). I just can’t get over how she champions her oral sex induced trade for Vick as being a determining factor for winning the league when she:

A) WORKS AT A DOG SHELTER
B) Bitched incessantly when that story broke
C) Never once offered me a hummer for Purple Jesus

Now I have to endure this awesomely slutty gal’s hypocrisy until August. Am I allowed to feel this way? Or should I just take my shameful loss in silence?

She works at a dog shelter and gives great blowjobs? If she’s also a dangerously imbalanced Latina, that woman is my dream girl.

To answer your question, there’s no hypocrisy in fantasy football management. I can praise Aaron Rodgers for being the foundation of my team in the same sentence that I hate him for submarining my playoff run with that Week 13 concussion. Just because I’m against stabbing people to death doesn’t mean I won’t gladly start the Ravens’ defense against the Browns. Shut up and acknowledge that you’ve been bested by a superior manager. Besides, you’ve finished in the money two years in a row. Most people don’t enjoy that kind of success.

Sex Second: In October I met a pretty cool girl through a friend. We met up for a Michigan State football game and she kept trying to make out with me in the bar after the game when we were both hammered drunk. I hate that. I just want to booze and yell shit at Wolverine fans in peace, is that too much to ask? Anyway, we eventually end up at my apartment and after some fooling around pass out.

I feel that in the morning of a hookup, it’s not improper to go for some morning action.

Not improper? It’s fucking mandatory.

I mean, don’t waste sack time right? Well as I’m reaching my hand down her underwear, I notice that she is really wet. I mean…monsoon wet. I was pretty pumped until I realized that my blanket she had wrapped around her all night is also soaked. Having been to college and been in similar situations before, I immediately realize that someone pissed the bed. My boxers were dry, leaving her the only culprit. When I quickly pull my hand back, she realizes it too. Trying to be a gentleman, I get up and ask her if she wants a drink. I bring her back a glass of water and she immediately “spills” the water all over my bed. I notice it’s an obvious cover up, but I’m too in awe of what’s happening to call her out on it. Needless to say she ended up getting out of there pretty quick. Cut to now and we’re dating. I’m terrified that in a drunken stupor I’m going to call her out on this. Should I save it for the inevitable time when I do something stupid to use as a “yeah but you pissed on my bed our first date”, or do I just bury the memory like that of every Redskins season since 1992?
Sincerely,
Pissed on in Michigan

You entered into a relationship with a girl who pissed in your bed on the first date. Your moral high ground isn’t much taller than a speed bump. Go ahead and talk to her about it sometime, but (a) not in the presence of other people, and (b) not as a trump card. If you bring that up out of spite, you’re going to do a lot more damage than you want.

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Dear KSK,
I quit playing fantasy football three years ago, I just don’t have the attention span to keep updating my rosters for 16 weeks, who am I Stephen Hawking?

I hope not. Although, on that note, it would be pretty awesome to be in a fantasy league with Stephen Hawking. The trash-talking would be phenomenal. “Hey, who’s Hawking gonna draft next? Mike Utley?”

On to the sex: I have been in a serious relationship for three and a half years, most of the time it has been long distance where we see each other once a month or more. But she is really amazing and makes it worth it, we are going to move in together in June and I cannot tell you how excited I am to not be receiving 75 text messages a day and waiting to smoke weed until after we talk on the phone every night. In the past year she has become worried about me watching porn, thinking that because I do she is not enough for me, and then comes the drunk crying phonecalls at 3am. She wants me to talk about it more with her but I really don’t want to say I love seeing random chicks take loads on their faces. She knows she is overreacting and is starting to see a psychiatrist this week so we will see if that helps. My question is the next time she wants to know about my porn habits what can I tell her to ease her mind?
-Not an Addict

Guhhhhhhhhh. I have no way of framing a man’s enjoyment of porn so that it sounds reasonable to an insecure girlfriend. In fact, due to my own ugly history with an invasive and controlling woman who flipped out over porn (and everything else under the sun), I have a hard time answering this with anything besides “RUN! GET OUT! GET OUT WHILE YOU CAN!”

But I realize that I’m projecting too much. Honestly, if she wants to know about your porn use, redirect the conversation: “Why? Are you unhappy with our sex life?” Because the way I see it, as long as you’re servicing her on the regular and keeping her happy in bed, then your porn habits are no business of hers. Even if you’re in a relationship that provides regular and satisfying sex, masturbation provides a welcome change of pace. And I think there’s nothing wrong with a little visual aid for that.

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O Captain my captain,

Gonna try to keep this short and sweet. Facts:
1. Girl at work – smart, witty, attractive…all around awesome. We flirt every once in awhile and get along great, but not sure if she likes me, though I think there is a good chance.
2. Sending flowers to her on VDay anonymously
3. Based on conversations in the past, she may be able to tell it was me who sent the flowers and based on her reaction i will decide when/where to ask her out
4. I am hanging out with a friend from college soon and if i want to, I can probably bang this chick. She is really hot, but i have no interest in dating her
5. I am a 22 y/o virgin, she is wayyyy more sexually experienced

I’m leaning towards not having sex with said other girl because I would feel like a douchebag if a relationship with the girl I like ever happened….but, I am tired of being a virgin and the stigma that comes with it. Am I being an idiot and is sending flowers to the girl at work anonymously a retarded play?
Thanks for the help,
Lovestruck in SF

God dammit, why must everyone try to date people at work? Stop it, all of you. Don’t shit where you eat.

Do you know what would happen if I talked to a 22-year-old virgin who chose not to have sex because he didn’t want to cheat on his not-girlfriend? I would slap that sonofabitch upside the head. Unless you are being sacrificed to a Norse god, there is absolutely zero value in being a virgin. Go out there and get laid.