Getty Image

Welcome to this week’s KSK Fantasy Football and Sex Mailbag. While Ufford is off in Paris with his lovely bride on vacation, I’m taking your questions in his stead. No need to waste time on the opener, let’s just jump right into the letters. Time it seems is a wastin’.

Captain Ufford,

From one championship fanbase to the next, please allow me to (belatedly) thank you and your Seahawks for this year’s dose of Peytonfreude, and avoiding the possibility of Fetusheadllatio all offseason. I don’t actually have a fantasy question, because I’m still trying to make sense of what the hell happened in free agency thus far, but congratulations Seahawks.

On behalf of the Captain, I will graciously accept your congratulations on the Seahawks Super Bowl victory. And what should you make of free agency thus far?

Getty Image

Exactly. It means what you want it to mean.

As for sex and relationships—well, I also don’t have an especially precise question; I’m just really at a loss as to where I am and what I am doing, and could use some general advice. I’ve always been terrible with women; I only had sex with 3 women in college, and none in the ~3.5 years since (a few random hookups here and there, but nothing further than that).

Not having a bunch of sex does not mean you’re terrible at women. It means you’re not having sex. Don’t get down on yourself something that probably isn’t true.

I go on a decent number of dates, because the internet makes it really easy, but nothing ever seems to come of them; I’m always timid and self-conscious because I haven’t had sex in a long time, so fail to make a move (I’ve literally been in bed with a girl and failed to make a move), and then feeling even more timid and self-conscious for having blown it.

Are you telling these women how long it has been since you last had sex? If you are, stop doing that. It’s none of their business beyond your assurances you’re not a typhoid carrier. Vaginas haven’t evolved to be behind women’s ears in the past couple of years, so no will notice it’s been awhile for you.

For what it’s worth, you’re working yourself up over something that probably isn’t a big deal to any of the women you are meeting. Honestly. I cannot recall a single one of my girlfriends (or guy friends) ever saying to me, “Well, I like them, but they haven’t had sex in an age and that’s a deal breaker for me. I like a man who I know has boffed at least 7-8 times in the last fiscal year.”

Last month, I had a date that just completely broke me. It was a great date, and we ended up naked in my bed without my even having to make much of a move (hooray for assertive women!), until, as I was lining up for intercourse after some mutual oral play, she said to stop . . .

But look at you! You were a complete gentleman and stopped.

and then left at first light the next morning . . .

Again, her. Not you.

and then said she didn’t want to go out again.

Still sounds like a her thing.

When I asked her point blank a few days later, she claimed that it nothing to do with my performance, but I honestly can’t think of any other explanation for what happened and she isn’t exactly talking to me anymore. Now, what little confidence I had left is completely shot, and I am feeling utterly hopeless.

Well, if she doesn’t want to see you anymore I can see why she wouldn’t want to keep in touch, but this still sounds like her issues. She was assertive enough that she knew she wanted some action, but not intercourse for whatever reason or reasons (and there could be a million reasons why so let’s not even try to guess why), and said it wasn’t your performance. Your response to the night seems a little heightened to you because it has been a little while since you last had sex, but it shouldn’t shatter your self-confidence. Really. If you had sex more recently, would you be thinking about this incident so much? No, you wouldn’t. If you were not so worried about the last time you had sex it would be just another, “Well, that didn’t happen. Oh well. Next!”

I just don’t understand what’s wrong.

Nothing is wrong. Promise.

I’m a smart guy in good shape in a big city full of smart, beautiful women (DC),

I’ve never dated there but from my understanding, DC a brutal town in which to be single.

I dress like an adult and keep myself well-groomed (I even floss for Christ’s sake), but I just can’t seem to find a woman who wants to be with me, and I don’t know what to do to change things. For the time being, I’ve appropriated the relevant parts of the Ufford Post-Breakup Plan™ for a General Get My Shit Together plan—I gave up alcohol for Lent to try to moderate my drinking habits, I am getting into a more regular workout schedule to go from being in good shape back to great shape, I deleted my dating profiles (except Tinder because of the lulz) to focus on schoolwork and self-improvement, etc.—but I don’t know how much that can really address my underlying insecurities. Do you have any other suggestions for how someone can try to get to a better place, or how to better approach dating from a position of low confidence? Alternately, do you have any advice on how to reconcile oneself to the prospect of dying alone? Because that’s really where I feel like I am headed right now.

Sorry if that was a bit rambling—obviously not in a great place right now,

-(Not That) Bill O’Reilly

If you’re just a few years out of school, it’s probably too soon to worry about the “dying alone” thing unless you happen to know about some secret government plan to implement LOGAN’S RUN in the next few months.

It sounds like you’re already doing all the things important to make yourself feel better; working out more, continuing your education, cutting out the oft-depressing dating sites. As far as self-confidence, only the worst egomaniacs have bottomless reserves of it laying around and nobody likes them. So fake it until you feel it for real. Stop beating yourself up over a calendar issue about the last time you had sex and remind yourself you are in good shape on the way to great shape, you are a smart person challenging yourself beyond college, and hey, you floss. Not to sound like your Nanna, but you are a catch. Tell yourself that even if you don’t believe it. Remind yourself of it before your next date. And the one after. Eventually, you find someone you can be completely insecure with (and be honest with each other about being insecure because how the hell can you not be on a tiny rock hurling through the vast universe!) and together you create one secure unit.

+++++

Hello, Special Guest Question Answerer (I’ve tried for like 5 minutes to think of a pun on “Sprague” and I got nothing. Sorry):

At least you didn’t try to make it match “ragù” or “Prague” and for that I am thankful. Sprague is pretty much a dead thud of a surname.

Anyway, my question is very minor compared to some of the weighty topics that are getting asked each week so I’ll keep it quick. I started seeing a girl a few weeks ago and we’ve been on a few dates. The first couple were just grabbing drinks; now we’ve progressed to dinner. All is well, except for one issue:

She never pays.

Oof.

Never even offers.

Really? Worst.

Never does that thing where you half-heartedly pull out your wallet, expecting me to tell her not to bother.

What the hell is wrong with her? Do you live in the south or maybe Texas? Does she have a rich father who made sure she never saw the cost of anything?

And when it was drinks, It wasn’t so bad, but I’m a broke grad student, and shelling out $70 for dinner and drinks for both of us really doesn’t jibe with my living-off-student-loans lifestyle. She, on the other hand is gainfully employed.

GAH! Give me her number, I’ll call on your behalf. But I won’t say it’s for you, I say I’m calling on behalf of woman everywhere in the case of  Stop Making The Gender Look Bad It’s 2014 You Make Your Own Money Spend It While Out.

I’d prefer not to blow up my spot, because I do like her, and although we haven’t had sex yet, I get the sense she’s not using me for mediocre sushi. What’s the play, here?

Honest to god, I have no idea what she’s thinking. I dated a guy for awhile whose family gets put on those Forbes lists and I still went for my wallet when we where out knowing full well he spent more the weekend before in St. Barts that I had made the ten years prior combined BECAUSE IT’S WHAT YOU DO. Anything less seems rude to me.

Maybe she’s had bad reactions in the past dating men also going through their salad days who felt emasculated by her being in a better financial position. But obviously you are a modern man who likes her despite her employment, so I don’t really know what to make of her actions other than to think she might secretly be in serious debt from school, bad car loans or credit card debit and she doesn’t want to come clean about it just yet.

Thanks,

[Witty play on the fact that I have $42 in my checking account]

STOP IT, YOU’RE KILLING ME

Well, you like her, so you’re stuck with still seeing her. But instead of going for sushi and drinks, suggest funky out of the way taco stands, the place you heard had the best banh mi, or dive bars with good jukeboxes that put out Pizza Rolls during happy hour. If she asks why you’re not going for sushi and martinis, be honest. “I’m a grad student and I can only splurge on that every so often because this one textbook cost like four nights of sushi and martinis.” If she’s really dying for sushi, maybe she’ll get the hint and offer to take you. Maybe it will be a relief to her if she’s secretly in debt that you’ll go to cheaper date spots she can at least offer to pay for and not worry about possibly hitting a $20 overdraft fee if her paycheck hasn’t cleared yet.

No one likes talking about money, especially when dating, but it’s okay to honest about being a grad student and what’s a “treat night” and what’s the more important “spending time with her night” before you go broke.
+++++

Dear Captain (or his squire, Sarah),

I prefer my given name, Princess.

I filed for divorce from my wife three weeks ago. I’m sure it was the right choice, but that doesn’t make it easy. Our main disagreement was on kids — when we first got together, she was 28, and I was 21. Neither of us wanted kids. But now that I’m 28, and she’s nearly 35, I’ve decided that I want them, but she still does not.

Yeah, it’s hard to say at 21 you don’t want kids. You don’t even know what you want on your pizza at 21. When I was that age, I thought I liked green peppers on my pizza. Silly younger me.

There are other things too, like a lack of intimacy and her temper. The latter, I’ve seen plenty of this past three weeks. She emptied our joint savings account (who knows where that money went), and she changed the locks on our house (even though there’s no restraining order, and I still live there). It’s been a “goddamn greasy nightmare,” as the Trailer Park Boys say.

Sounds like you’re getting away from a whole bunch of issues, which is good.

Anyway, my question is, what’s next for me in the future? I know I should wait a while, but when do I start dating again? HOW do I start dating? I feel like I’m a lot less interesting than I once was.

Well, you have spent the last seven years in a routine with someone else. It’s not that you’re not interesting, you’ve just become accustomed to what’s around you which only makes you feel dull, but that does not actually make you boring. When you start dating again is entirely up to you. If you don’t feel like waiting, don’t wait. They’re dates, not blood committed pinky-swears.

I’m a very indoorsy person, and it seems like every person on these dating sites (or apps) enjoys things like sky-diving and skiing (even though it never snows here in Houston). I am not a drinker at all and it seems like the rest of the world IS. I have no earthly idea how to dance. I have a great job as a writer, I can play piano and violin, and I like to think I have a good sense of humor, but is that enough? My qualifications seem more like a medieval courtesan than a “real Texan man.” Hell, I’m not even a real Texan — I’m originally from FLORIDA for fuck’s sake! Where do I go from here?

Thanks,

Please God Don’t Use My Real Name

Of course all of those things are enough. I don’t know what a “real Texas man” is other than maybe they wear armadillos for shoes, but I do know Houston is a fantastically large city so odds are you’re not the only non-Texan living there. There is probably good a portion of woman who are tired of real Texas men and their armadillo shoes, so it’s not an entirely hopeless situation.

“Have a great job as a writer” is a surprisingly a strong aphrodisiac to a good part of the female population. Go to readings at book stores, become a regular at museum events (even those “art after dark” things even if you’re not going to have a cocktail), spend time at the local art house cinema. When you feel you’re ready to date, you’ll already have a good lay of the land of interesting, non-boring events you that appeal to you and make you feel engaged again. My guess is by then you will have met at least a couple of woman into the same indoorsy things you are that would be interested in a date with an employed writer looking to have kids.

Don’t force yourself to be an outdoorsy person just because everyone on a dating site says they’re outdoorsy. (In my experience, most people who say they’re “outdoorsy” really mean they like to go for an easy one to two hour hike and then stop for margaritas at a patio bar the way home. Saying “outdoorsy” is a good way to hide the fact they spent the previous weekend mainlining three seasons of “Breaking Bad” without leaving their bed but left the window open.)

+++++
Hey there, Captain,

Not the Captain, but I’ll take it. Little known fact: I once worked for a water taxi service in Ft. Lauderdale and Miami. Boat captains used to get really mad when deckhands where called captains by the tourists.

I’m a freshman at a major university and I have no idea how to get with girls. I think I’m a fairly personable guy, I’m definitely not great looking but I don’t think I’m repulsive either, and I’m out of shape but not obese. The thing is I’m not horrible with girls in a regular situation; I can get along with them without looking like a complete jackass, but I just have no clue how to get a girl to hook up with me. It really sucks being the only one of my friends who is still a virgin, especially when I’m getting no play at all. I was wondering if you had any tips.

Sincerely,
A boy who seriously needs to get laid

There is no miracle way to get a girl to hook up with you, especially in college when women your own age are also rather inept at socializing. In my experience, there are large groups of young people shipped off to college who never really learned how dating worked in high school for whatever reason (although for me it was because many of them had a Catholic school background which added a whole other level of inexperience into the mix), and freshman year was like a big step back to middle school behavior.

First off, don’t worry about who is a virgin and who isn’t. Much like the first letter at the top of today’s column, your past sexual experiences only matter in so much everyone is healthy and not going to give each other debilitating diseases, and even then you only need to discuss this with someone you are actually going have sex with. Why do I say this? Because even 19 year-old women are keen enough to tell when a guy is only looking to get laid so he’s no longer a virgin and unless they’re the type of woman who gets off on being firsts (and they do exist), that quiet desperation is a terrible vibe.

Your second step is to relax. You get along with women just fine in normal situations, so take the same attitude and sense of humor to social situations. You’re a freshman, so join as many clubs or what have you as you can without destroying your schedule. You’ve got much better odds at connecting with someone in that setting than in the groups of 12-20 of freshman who tend to herd together on trips to the dining hall or bars with lax serving policies.

And finally now that you’ve relaxed, you’re in a lower pressure environment, learn to flirt. The art of smiling at a person you may possibly be interested in — or not, the best part of flirting is you can decide ten seconds in they’re not for you — and saying something completely off the cuff. And then learn to really flirt with a woman using humor, casually touching their arms or knees when telling a story when it seems appropriate and if they’re responding to your flirting. The rest progresses from there.

+++++

Hello Captain,

Fantasy First: My only real question here is what to do about Doug Martin. Obviously he’s done for the year and I should probably cut him, but this is the first time I’ve done a keeper league and I’m not sure if I should keep him for next year when he’ll be healthy and Schiano will be fired which can only do good things for him.

I’m not sure what advice Captain would give here, but I would personally cut bait on Martin. I don’t think the Bucs are going to be in much better shape next season (the stink of Schiano is going to take more than a few months to wash off) and while he did have a great rookie season, it’s just too much of a gamble to hold on to him this year after injury. With Rainey and James right there with Martin, Tampa’s looking to move to a running by committee game anyway. Even if Martin is 100%, he’s not getting every carry.

Sexy time: I’m a freshman in college and don’t really know how to get with girls at all. I hooked up with a few girls in high school, but it was nothing more than making out. I’m certainly not a great looking guy, but I don’t think I’m repulsive either. I can talk to girls okay in regular situations, but I just have no idea how to try to get them to hook up with me without me seeming like a huge creep. Help me, oh wise one.

Sincerely,

A sexually frustrated 19 year old.

See the advice I gave to the guy above? Same thing. Relax, flirt and let it progress from there. Men who flirt and make a woman feel at ease are much less creepy than guys who just jump whenever they feel like they have an opening.