KSK Mailbag: Terrible advice for dating your co-workers (or anyone)

04.24.14 3 years ago 44 Comments

Hello and welcome once more to the KSK mailbag! Nice weather we’re having, isn’t it? OH GOD WE’RE CHATTING ABOUT THE WEATHER JUST GET TO THE SEX.

Very well. Let’s get to your questions. As always, if you have something for next week’s mailbag, email us!

Dear KSK,
Sex: I work with a girl who’s incredibly intelligent, beautiful and has a dry, dark sense of humor that I really enjoy. I don’t know her especially well, but we have very similar tastes and our conversations seem to have become increasingly flirtatious. As an example, the other day she was complaining to me about being single and how difficult it is to meet a decent guy. I may be reading into this too much, but she is stunning and I find it very hard to believe she actually has a hard time meeting guys. I’ve been dishing out subtle compliments to her and she’s been responding in kind. I know your policy on workplace relationships and I generally agree, but she only works there occasionally and we see each other maybe once or twice a month.

Game on, says I.

It seems like the potential damage if things go poorly is limited to my own embarrassment and sporadic awkwardness. I have a hard time reading women in these type of situations (I’ve gone both ways, making apparently inappropriate advances and also ignoring insinuations, then being told they were flirting with me after it was too late)

Oh, so you’re every guy on the planet.

and I’m not sure if I’ve given you enough information to work with, but I wanted to hear your opinion on whether it’s worth the risk of asking her out. The job isn’t super important to me career wise, but I like the people there and I don’t want them to think I’m sleazy or have to find another job right now. I’m pretty heavily infatuated with her, but I just can’t decide whether or not to pull the trigger and find out if my feelings are reciprocated.

While it’s true that I’m generally against dating people you work with, there are TONS of exceptions. I take that stance with the assumption that you have a career you like and an attractive co-worker you couldn’t avoid if things happen to go south. It’s not the same if you’re just in a job and your crush is only there intermittently. Like, if you’re working at the frozen banana stand for the summer, then by all means hook up with your attractive co-worker. That’s the best perk you’re gonna get.

That said, you still need to handle the situation delicately. Work is a weird place to ask someone out. Maybe you can organize a happy hour with some co-workers you like, then invite her to be part of the group. That will give you a chance to interact with her in a more informal environment, and a beer or two will help ease the stress of asking her out on a date. And if she says no, it’s not a big deal. You asked her out at a bar after a couple drinks, which is a way more appropriate scenario for doing so than in the communal kitchen hoping that no one else walks in on the conversation.

FF: Keeper question; Eddie Lacy for a 2nd round pick, or Randall Cobb for a 12th? Cobb is obviously better value, but he seems fragile and I’m not sure what sort of role he will have this season. Lacy seems like a durable RB who should be drafted in the 1st. What do you think?

Eternally Indecisive.

Lacy is definitely a first-rounder this year, but Randall Cobb will be fine. I’d probably take Cobb simply because you’re getting a premium wideout — 4th round value, give or take — for a 12th rounder. As much as I love having reliable, workhorse running backs, I think the better way to build a solid fantasy team is to steal value from the back of the draft wherever possible.


Fearless Leader,
I’m a long time follower, and look forward to your mailbag each week. Unfortunately, I don’t have a fantasy question, so hopefully this picture of Anne Hathaway will serve as penance.


Ah, Anne Hathaway. She’s so delightful in still-picture form.

Relationships: About 4 years ago, I moved to a small rural town to take a job I love. As you can imagine, I quickly saw how limited the dating pool was, especially if you start eliminating people who have criminal records, and other less than desirable traits. So when I met my current girlfriend a little over a year and a half ago, I was positive that the other shoe would fall any day. Luckily for me, it hasn’t and I’ve only learned more and more about how awesome she is. She comes from a great family, has a job that really lets her make an impact in the community, she’s gorgeous, she’s really smart, and the sex is amazing. We get along great, and spend almost all of our time together. Not to sound corny, but she’s the full package. For the past six months or so, I’ve been thinking more and more about marriage, but always backed off the idea because of how expensive rings and weddings are. That said, after listening to some sage advice from a few older co-workers and my parents, I’ve finally decided to stop making excuses, and have saved up enough money to buy a ring (Yay, me!).

Oh. From where this started, I thought your story was going to take a turn for the depressing. I am simultaneously happy for you and sad for the mailbag.

And there is where the problem comes in. I have some ideas of what she wants ring wise (cut, type of gold, size, very general style…), but I’m scared shitless I’ll buy one and it won’t be right. I mean, if she says yes, she has to wear the thing the rest of her life, and I want that to be a good thing. She is already on pins and needles about wanting to be married (Her roommate gets married in just under a month) so I am worried about asking any questions that might give her clues that a proposal is coming. Also, she can be the anxious type, so if I come flat out and say “Hey, I’m ready to buy you a ring, come give me some ideas of what style you want… ,” she will drive herself bonkers stressing until the point in time where I ask the question. Seeing as to how you’ve been there before, do you have any advice on how to go about this without ruining the surprise? Should I just call up one of her close girl friends and pick their brain, or should I go to the jeweler with what I DO know and then do my best to find something that looks great within those parameters?
Thanks in advance,
-amazingly witty nickname that hides any trace of my real identity

This is a very common conundrum for the soon-to-be affianced male: finding a balance between surprise and ring satisfaction. And let me assure you: ring satisfaction is WAYYYYYYYY more important than the element of surprise. If you can’t suggest some casual ring shopping — for, you know, some indeterminate time in the future — then enlist one of her friends to take her around. Don’t let her be obvious about it, either. It should be a girls’ brunch — or whatever they have in rural towns instead of brunch — that turns into a “Hey, let’s go look at jewelry!” after they’ve had some drinks. Then she can report back to you with her findings.


Hey Matt,
Last year I grabbed Jordan Cameron in the 15th and felt pretty good about myself for a decent part of the season. I’m starting to plan my drafts, and going to try and pick up Zach Ertz and Travis Kelce in the late rounds this year. Are those two good to target, and can you recommend any other upside/sleeper TEs?

I doubt he’ll be available in the late rounds, but the Chargers’ Ladarius Green seems like a decent option, assuming the wheels finally fall off Antonio Gates. And of course there’s the new crop of rookie tight ends. But who are the best tight ends in the draft? IF ONLY SOMEONE WOULD MAKE A VIDEO TELLING YOU EXACTLY WHAT YOU NEED TO KNOW.

Ah, how convenient!

(By the way, if you happen to not hate that video, Dan Rubenstein and I have been covering mock drafts, team needs, and draft prospects every week on our Future Consideration show. This is the end of my plug.)

Sex: I had a bad breakup a while back, and recently got over it with a late implementation of your plan. I’ve gotten over the idea that all women are evil and out to get me, and am trying to get back on the horse. I haven’t had much luck with girls in a while, or been on a date/gotten laid in a couple years.

During that time, I graduated college and am living with my parents looking for a job, so I don’t get out much. I’m not really sure how to get back into it, specifically worried about not being laid in a couple years and being bad/rusty/generally inexperienced at sex. Is that a legitimate concern (or am I overthinking it?) and do you have any general advice about getting back into dating/relationships?
Thank you,
Late Round TE

The first step is embracing who you are, and loving yourself and your situation, even if that doesn’t feel particularly sexy. The best armor against someone judging you or writing you off because of your work or living situation is to not give a shit what they think. I’m not suggesting that you be one of those deluded weirdos who talks about how awesome it is to live with their parents (“It’s practically my own apartment, rent-free”), but there’s a self-deprecating line where you can acknowledge where you’re at without being a sad-sap Woody Allen type.

Of course, it’s hard to get out there and meet people (and buy drinks) without having a job, so the best way to get out of the house is to find reasons to get out of the house. Personally, I think volunteer work is the best and most rewarding way to do this — you’d be astounded at the number of education, animal, and veterans non-profits could use an extra hand — but you can also just make plans to meet up with old high school or college friends. Just being out and social will give you the boost in confidence you need to talk to the occasional lady. Relax: you’re young, and there’s a lot of living left for you.


Dear KSK,
No fantasy question today, so instead I offer this picture of Miranda Kerr:

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I appreciate this, I do. I also want to point out that it feels strange to “accept” photos of sexy women as your penance for not having a fantasy football question, as if I’m some Old Testament deity to be quelled with tits. For the record, I’m happy to look at — and publish — photos of attractive women (or men… ladies) — but you don’t need to produce them in lieu of a particular question.

Okay sex question: After breaking up with an ex (with your advice helping me to get the eventual decision) I went a bit crazy and chased anything that moved and got my fill. After hitting for the cycle (black, latin, white and red head) I went on a self imposed sexile because, well I felt dirty and that I was spiraling a bit out of control.

I hope that you only referred to it as “the cycle” because you know that this is an anonymous forum and were trying out a new phrase. PLEASE tell me that you’re not equating women of different skin colors with stats to be collected. Furthermore, if you’re going to be so shallowly pig-headed, don’t make redheads and white girls different categories while excluding Asian girls altogether. (I’ve heard their vaginas go sideways!)

Aside from being reductive about race and ethnicity, “the cycle” is also a confusing affront to one of the more lasting sports/sex metaphors: reaching first base, second, and so on. Like, I hit for the cycle with my wife on a semi-regular basis. You can’t just up and make it about sleeping with different kinds of women. There’s a linguistic history to respect.

So, I cut back on the drinking and random hooks ups and have been focusing on things that makes me happy and have since met some very interesting girls. Not to mention I have friends who are trying to set me up (side question, is this a bad idea?). No complaints from me on this.

Not a bad idea. If you’re not dating anyone, go meet new people. If you like each other, try having sex with each other. There’s no reason to feel guilty about that or to limit your options, as long as you’re being honest with the people you see and not juggling a cast of girlfriends.

Where I’m struggling is that while I’ve met and gone out with some very interesting and attractive women, trying to talk to them through text messages is not the easiest thing to do. It eventually progresses to so much contact that you run out of shit to say. So what’s the rule on how much contact is too much?

There are no rules. If you’ve run out of things to say, then you’re either (a) not that interested in her, (b) not very inquisitive, or (c) somehow incapable of texting, “Hey, I don’t really love texting — can we just talk on the phone instead?”

And since I’m lazy I’ll throw in an unrelated question. What’s the best way to stop talking to a girl you’re no longer interested in? Apparently women really hate it when you try to fade out/ignore. I’d like to remain on good terms, especially if it was casual, but I also don’t want to lead them on.
-Getting Back In The Saddle (yes I live in Texas)

“I met someone else.”

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