The KSK Mailbag: Dating Your Coworker, Date-Dates and Weekly Fantasy Leagues

10.23.14 3 years ago 108 Comments
Dating A Coworker


Ufford, after years of taking his own advice about relationships and sex, has achieved starting another human life with his wife this week, so I’m filling in for Mailbag duty while he watches the baby and waits for the umbilical cord to shrivel up and fall off.

Human life, it’s pretty gross.

Hey Matt,

Third NFL season I follow you on twitter, SBNation and here keep up the good work. Football first:

On behalf of Ufford’s ego, I will accept this compliment.

This is my first season betting on Fanduel and Draftkings, do you have any advice with drafting teams? I generally try to pick up a few bargains and then a couple “reliable” players like DeMarco or Antonio Brown based on match-ups.

Now, I haven’t played in these style of leagues because they seem too close to sitting down at a blackjack table in Vegas where I may have a minuscule edge, but ultimately I am going to lose all my money on because of some terrible beat like someone playing Chris Ivory when I have Arian Foster.

This guy’s logic is probably close to what I would follow, but I am not sure if it is the best plan for him so I asked Ryan Hester of the FootballGuys for some help with this question. Here is what he had to say:

There are two styles of play in Daily Fantasy Sports. “Cash Games” are the more conservative route, and “Guaranteed Prize Pools” (or GPPs) are the way to turn a small entry fee into huge bucks. Obviously, the odds are different in each. Cash Games include head-to-head matchups against one opponent or 50/50’s, where if the group is 40, the top 20 get paid the same amount.

In Cash Games, you don’t want to overthink the room (mainly because it’s a smaller amount of opponents, and coming in 20th out of 40 is the same as coming in 1st. In these games, it pays to find players with high floors. Spending a little more on QB to get an elite option is generally more advisable here. Paying a little extra for a player like Antonio Brown (particularly in DraftKings because it’s full PPR scoring) is also a smart move.

In GPPs, a good strategy is “stacking.” If you think a WR is going to have a huge game, pair him with his quarterback because if the former performs well, the latter is also doing so by default. Pairing Joe Flacco and Torrey Smith two weeks ago would’ve been a great strategy in a large (multiple hundreds of entries) GPP because they weren’t owned by many people, and they both produced in a huge way.

Ultimately, though, regardless of contest, pay for volume. At WR, spend a little extra on a guy like Brown who is averaging 10.5 targets per game instead of trying to go cheaper for someone like DeSean Jackson who could have a huge game but also only sees an average of 6.7 targets.

At RB, look for pass-catchers. For example, in Weeks 5-7, Ben Tate had a solid 63-237-2 line. In that same time, Branden Oliver had a 60-282-2 line. Oliver was 5th in PPR scoring, while Tate was 18th. The difference was Oliver’s 10-102-1 receiving line while Tate had just two catches for -4 yards.

That all sounds like good advice to me, even if you are not currently playing in a weekly league. If you are thinking of joining DraftKings, use this link when you deposit and find Ryan at RHes13 to challenge him in a contest, but I offer no guarantees on how you will do and would like to clearly state that I am not in fact enabling a new fantasy football obsession.

And onto the personal:

I’m in a great relationship but we are stalled out because we work together. I’m in process of trying to move onto a better job (for a number of reasons) but till then we can’t make it public or take any more steps forward. I don’t mind it, but it seems to be affecting her lately. Any advice? I should point out, this is the first time I date a co-worker seriously.

When you’re starting out a in great new relationship, you want to shout it from the mountaintops. Extra bounce in your step, laughing at stupid inside jokes your lover texts you during the day, a compliment on a vintage $5 necklace you found for her while getting coffee together on Saturday morning from a coworker that can be coyly answered with, “Oh, this? My boyfriend bought it for me over the weekend? Isn’t it cute?”

People having a good time don’t like to having to hide their glow. It’s a bummer when on Monday when your cube mate asks you how you spent your weekend, you can’t say you went for coffee on Saturday morning with a new beau because obviously you spent all Friday night together boning or playing drunk Scrabble or perhaps both, and you have to lie and say you hung-out with just your girlfriends then grouted the tile.

This isn’t braggy, it’s just part of enjoying that someone finds you special and all part of the pretty socially normative dance that you have been coupled with someone else.

Since you’re already working on the part of finding a new job so neither one of you have this hanging over you (among other reasons), my best advice is to just make sure when you are together, you do everything you can to make those moments feel even more special and precious to makeup for all the times she’s putting her proverbial light under a bush. Talk to her about it, tell her you appreciate that this is rough to keep your dating a secret for now and how you can’t wait to find another job so you don’t have to hide your relationship away.

For some people, just the weight of a secret — any secret, good or bad — brings them down over time. Hopefully this burden will lift from her soon and she can brighten right back up.

Also, we all share a lot of our relationship and personal issues here but I’ve always wondered if you’d share a bit more about yourself. I understand you have a military background and are married, anything you’d want to share?

Thanks for your time,

Since I’m not comfortable about sharing anything about Ufford’s life other than I’ve seen him wear a fedora, you’re stuck with mine.

I’ve been with my husband for nearly twelve years, married for six and, no we don’t really account for the six months we broke up in the middle of it all seven years ago. During that time we both dated other people, I briefly got back together with an old boyfriend, but generally we were pretty miserable broken up (funny enough, we broke up because he had been pretty miserable to live with, all work related stress, and I grew exhausted at the end of each day having to make his life better while still dealing with my own shit) and realized we were much happier together and missed what we had built with each other. He got better at bringing work stress home (still an ongoing project), and we recommitted.

Before my husband though I had two other long term relationships (defined by being more than two years) that didn’t work out; one because we were young, poor and immature, the other because he did not want to have kids and I wasn’t ready to take that off the table. That last one was heartbreaker and one of the reasons I left the city I grew up in (my boss at the time looked at him and said to him, “You jerk, how can you let her go? You are the reason we’re losing her.”), but we’re friends and I am happy to say he and my husband get along just swell when we see him. Few other great guys mixed in who didn’t work out for various reasons, few casual relationships and more than my share of hook-ups and one-night stands.

While I was never in the military, my life has been a hodgepodge of various jobs (in no particular order), from camp counselor to special needs kids to kitchen store manager to gourmet shop baker to boat hand to [redacted] to comedian to sports merchandizer to historical society employee to [redacted] to coffee slinger to record label operations manager to writer to editor to production to [redacted] to non-profit grant writer to whatever it is I do now; professional manuscript reader, KSK contributor and front page editor and curator for Yardbarker.

Oh, and I have an Etsy shop where I make jewelry and cufflinks out of old trading cards.

Stay busy, never stop hustling. (And don’t study Latin in college unless you’re really serious about that threat of going to law school.)


Dearest Matt,

Fantasy: My team is doing good (3-3 despite being the highest scoring team in the league), and I’m riding the Demarco Murray/Gronk train as far as it will take me.

I made fun of people in every league I am in for taking Gronk because of health issues, but it looks like he might actually make it the full season this year. DeMarco Murray is having a monster season for Dallas so far (yeah, yeah, soft schedule), so it looks like you should continue to have the most points in the league. Some people like to set up their league playoffs just on points for the situation you are in right now, but I personally prefer when leagues are more like actual football. Sure the Seahawks and Jets put up 26 and 25 points respectively last weekend, but they still lost.

Sex: Somewhat out of context, but a couple weeks ago (, last one down) you gave the advice to present yourself as more than a friend when talking to women and whatnot. Could you expand a bit on that? I’ve been trying to wrap my head around it and I’ve got nothing.

Let’s get in our wayback machine for a minute and revisit:

SEX: I’ll try to keep this short. Had a class with this gorgeous girl last year. Waited for an opportunity to talk to her, but she only showed up half the time, often late/left early, was super quiet, sat in the back corner and kept to herself. Told myself in the last few weeks I’d man up and just approach her, but I missed a few classes at the end of the year as well and never saw her. However, by a stroke of luck I happened to run into her in the hallway when visiting my prof’s office hours before the exam. I seized the opportunity, we started to talk and it turns out she’s smart, funny, and really friendly, and we hit it off. She said people tell her she comes off as unapproachable but she’s just really shy and awkward around new people. I told her I was meeting some people to study later that week, and she said she’d love to join us and gave me her number.

That’s wonderful! Could you please hold a seminar for all the other KSK mailbag readers who can’t speak to strangers?

So she comes out to a couple study sessions… now like most guys I’m usually hopelessly oblivious as far as picking up on when a girl is into me, but this girl is clearly flirting with me, and we continue to hit it off. The exam comes up, and a group of us go for drinks afterwards. We have a few beers and she’s flirting even more. BUT… as we’re getting ready to leave, I ask her out and she says something like ‘you’re really cool, and I’m not in a relationship right now but it’s kind of complicated and I need to figure ME out right now. So I can’t really say yes, but I’d totally be down to hang out again sometime.’ I interpreted this as some guy she likes is jerking her around but could mean a whole lot of things (including exactly what she says it means). We also had both mentioned we would be traveling for the bulk of the summer so it wouldn’t be a great time to get involved with someone. Anyways, I texted her a couple weeks later asking if she wanted to hang out and she never responded so I left it at that.

That was back in May, so last week I decided to text her hoping May was truly just bad timing. She responded very quickly and we’ve exchanged a few friendly texts over the last week. So now I’m wondering how to proceed. She knows I’m romantically interested and I’m fairly certain she is too, so I’m tempted to just straight up ask her if she’s seeing anyone and if she’d want to get together. But I was confident that was going to work in May and it didn’t. Is approaching this from a more friendly angle a better play? Or should I just go for it?
Draft Day Disappointed

If you’re interested in her romantically, don’t present yourself as just a friend. Present yourself as someone who is doing her the favor of giving her a second chance at YOU, Supremely Confident Attractive Human. CONFIDENCE, COHEN. Eye contact. Wry smiles. Direct questions. (“So what WAS your mysterious situation last spring, anyway?”)

I’ve also found that it helps to go in with ZERO expectations. Whenever I felt out of my league, I’d adopt a mindset of “Well, this isn’t gonna happen, so I’m just gonna be myself and say what I feel.” Then BAM! Every set of underwear within a square mile of the bar we were at disintegrated. Even the guys’.

True story.

I’ve said this in many a mailbag, but this is where dating in college completely blows. Any situation is possible “let’s just hangout as pals” and any situation, even going to lunch together between classes is a possible date. It is, and always has been, complete bullshit.

Because any interaction in college can be a possible hangout as friends or a possible date, you have to make it very clear YOU WANT A DATE. Even if you are too nervous to say “date” because you don’t want to scare her off because of whatever situation she was in last spring, you have to say, “I’d like to take you to…” then “would love to catch up on your summer” and then name a spot that people ONLY go to on dates around your school, generally some inexpensive red sauce Italian joint with candles in chianti bottles because you’re in college and those are the only somewhat romantic spots in college towns. (I was lucky enough to go to college in an Italian neighborhood in NYC, so at least those cheap dates had halfway decent food.)

The location of your get together will, if you are not going to say it before you are actually there, is going to at least send the message this is a date. Everyone knows the dates places around campus. Make it a day of the week that people generally go on dates, don’t pick a random Monday. All of these clues will at least say, “HEY I AM TREATING THIS AS A DATE.”

If she’s not interested or maybe unsure, she’ll probably defer to something more casual like getting a coffee. Get that coffee with her, catch up on her summer, take Matt’s advice and if the moment feels right, ask her, “So what was going on last spring?” You might be in for an earful. Just listen. At the end, if you are still interested and it seems like she is open to seeing you again, say the D-word. “It’s been great catching up and I really like hanging out with you. I’d love to take you out to something more than coffee, maybe dinner later this week.”

And if she’s really not interested, let it go and move on. Following her back and forth for clues about what she is looking for is just going to make you crazy and life is too short and filled with many women who will jump at the chance to go out with you.


Duchess of Fantasies near and far,

You are too kind.

No football related question this time.

Good, because my fantasy football season is now a wasteland due to a last second trip out of town. Goddamn real life getting in the way of my fake life.

Sex: I am having a moral dilemma, I have a very attractive female acquaintance of a few months now. She is married, but has been asking me to hang out and all but said things are gonna go down. I have expressed reservations about her martial status. She says it is her problem and that I shouldn’t worry about it. However, I feel bad still. She claims that they are all but separated and that she has no interest in him anymore. She is a lot of fun, I think I genuinely like her, but I don’t know how to precede going forward. Thanks in advance for your help, feel free to reword this questions if it helps to make it easier to use.

Johnny Football

This is what I have found, sex you even feel a little bad about or even a little guilty over because of another person’s situation in the end, sucks. You might like that person, but the crappiness of knowing there is something else emotionally going on in their lives that is unresolved (and you know, separated people end up hooking up all the time, so you really don’t know what is happening on that front) really puts a pall on the whole thing. I’ve been involved with two men going through separations, and it really didn’t feel great to be the third wheel, even though they both got divorced. (It’s especially not fun when the spouse of one of them, in a moment of spitefulness over the crumbling marriage calls you and leaves you a ten minute voicemail telling you all the things they know about you from their “separated” partner. Now you’re a part of whatever drama they still have and who needs that.)

If you really like her, wait for the divorce no matter what she says about it being her problem, because that’s the quickest way to make her problems your problems that I can think of in a relationship. Did you read the part I wrote above to S about myself and the brief breakup I had with my boyfriend-now-husband? I too told guys I was seeing in that time I was separated from him and we still got back together, and that hurt some people’s feelings in the end, and that was not fair of me. I should have just been with myself and waited until everything truly was in the clear.

And lastly from Twitter:

@sarah_sprague I have many extra habaneros which I need to use soon. Should I freeze or is there something better I should do? No other q.

Boy do, I hear you. This is just part of what my peppers look like now (you can see in the background I have already pulled up my tomato plants for the season). Raised garden beds because if I don’t my dog will eat everything.



I’ve already been been drying out serrano peppers all season, frying my jalapeños like crazy if you remember last month’s Foodball, and now I’m going to get ready to start taking care of my tabasco peppers. Going to pickle some and then dry some to make red chile flakes.

Since I generally only put habaneros in my guacamole because I’m a big wuss when it comes to heat in my food, freezing them (stems and seeds removed), sounds like a good idea since if they be soft once you thaw them and who cares, you’re going to roast them for gauc. But have you thought about air-drying them or drying them in a warm oven (about 200º) for a few hours so you can make your own dried chile powder? That way you can add it to whatever you want just a few dashes at a time.

I know we have a lot of people who do their own gardening around here (surprisingly for an NFL dick joke blog), so I’ll open this one up to the class for further suggestions.

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