KSK Mailbag: How to avoid small talk on first dates

05.29.14 3 years ago 150 Comments


We got it ALL today, folks. As always, if you have a question for next week, email us here. Let’s get right into it.

Hey Cap –
Lady reader here. I had no fantasy team last year because my friend hosed me. How do I get back at her?

Tell potential suitors she has herpes. OWNED!*

*do not do this

So dating is the worst, and I’m kind of a late bloomer, so I feel like I never really learned how to do this. Like, what do people generally talk about on dates? I’m good at small talk, thanks to my job, but my dates recently (yes, I’m trying online dating) end up feeling sort of like job interviews. How do I change up the vibe to make it more fun? What do guys like to talk about on dates? Any tips for thoughtful questions that are more revealing than ‘what do you do’? I’m in my thirties if that changes things.

Well, a first date kind of IS a job interview: you have to provide an outline of who you are and what you like so there’s a base for communication. That said, if you’re online dating, you should be able to dispense with some of that basic information exchange before you ever meet IRL. Or if you want to spice it up, open the date with “Listen, I hate small talk. Let’s each talk about ourselves for one minute, then no more small talk the rest of the night.” Then put him on the clock.

After that, the key to breaking out of that rote “job interview” discussion is to find common ground. What are you both passionate about? Indie rock? Travel? Dogs? Tacos? Find that touchstone and use it to propel the discussion forward: what’s the best taco he’s ever had? Carnitas or al pastor? Is the Doritos Locos Taco brilliant or a crime against humanity? And “Hey, if we decide we like each other tonight, we should get tacos at [taco place you enjoy].” You learn more about a person by going in depth on a single subject than by getting a broad overview of everything.

Also, what’s with dudes who pursue someone and then just disappear after getting naked with that someone a couple of times? My first assumption is always just that I’m bad at sex. Men, please stop doing this. Just tell me you’re done so I can move on.
Thanks for your insights,
15 Weeks ’til Football

There are certainly men — I’ve been guilty of this — who consider sex to be part of the vetting process. But the more likely explanation is that for most men, their desire for sex with a woman trumps their interest in a relationship with her. It is totally shitty and unfair, and you definitely deserve a “Thanks, but I’m just not interested” phone call. That, however, is a fact of dating I can’t change. All I can tell you is: it’s not you, it’s them.


Dearest Matt:
Fantasy: I’ll try not to bore you with the details of my keeper leagues setup, but essentially I need to figure out which players from my roster are poised to have top 20ish seasons: Josh Gordon (would be a lock but I imagine they will be some resolution by late August), Andrew Luck, Matt Stafford, Andre Ellington, or Julius Thomas?

I’ve seen rumors of Ellington getting 25-30 touches per game this coming season, but I find that highly improbable. Still, an increased workload would make him a tantalizing dark horse. Depending on whether Josh Gordon gets reinstated, I’d rank Stafford and Thomas as the surest bets for 2014, followed by Ellington, then Luck. (Luck is terrific and adds nice rushing value, but I’m not as smitten with him as the typical fantasy player).

Sex: I’m a 26 year old guy who has very little relationship experience and hasn’t been the most popular guy with the fairer sex. Most of my life this hasn’t been a huge deal because I’m not interested in flings and I’ve enjoyed doing whatever I wanted, which for a long time consisted of getting way too drunk and having laughs.

That lifestyle, wow raucously fun during college, started to take its toll when I found myself hungover way too much, underpeforming at my job, smoking way too much weed, wasting money, and not really making any meaningful progress towards the really worthwhile things in life. Not to mention loneliness starts to become a thing as seemingly everyone you know starts to get hitched. And I’m at the age where I would like a meaningful relationship (as mentioned earlier, casual sex is worthless too me). Plus, these are in all likelihood my most energetic years. I’d like to spend them with someone I love.

So about a year ago I started to follow your self improvement plan. I work out regularly now, cut way back on drinking, eat better than 90-95% of people I know (not really a feat in Buffalo, NY), started kicking ass in my job, and working hard towards gaining advanced education to further my career (which is really important to me).

Overall, this has done big things for my self confidence, as I know have a much clearer sense of self and what my best qualities are. However, I haven’t really seen this life momentum translate into any real progress on the dating front. I don’t get a ton of opportunities to meet women (most of my friends aren’t single), and when I do, my lack of experience seems like it prevents me from taking any real chances. I’m below average at reading signals, but even if I were to sense a girl was in to me (not a common problem for me) I wouldn’t have the first clue of how to moving things forward without coming off like a pathetic creep.

My question is, what’s the best thing to focus on the moment? Should I be finding a way to meet more girls, or do a better job with the ones I do interact with? Or if I keep working on myself (which will happen anyway, feels too good not to) will things fall in to place naturally?

I feel like a variation of this question has appeared in the mailbag every week for three months, so I’ll keep this short: Internet dating. Get on Tinder and/or OKCupid (or Match if you’re more serious).

Also, don’t live in Buffalo.


I’m in a two keeper league but had a terrible year after going all in on CJ Spiller and have no other real value to speak of. I don’t have a question, I’m just seeking sympathy from internet strangers.

I’m sorry, we’re fresh out of sympathy today. Will you settle for some derision?

Sex – I recently starting seeing someone who is smart, attractive, talented, interesting, and so far not the slightest bit annoying. She’s also been sober for a few years – she’s struggled with alcoholism in the past and has seen some bad stuff in her family. I’m not the drinker that I was in my early 20s but drinking is still a big part of my social life. I also think that few things are as fun as sharing a bottle of wine with a lady and then having some sloppy, sloppy sex.

For what it’s worth, she says she doesn’t mind being around drinking. I respect her decision and the strength it must take to be sober, but this is uncharted territory. Since your wife doesn’t drink either, do you have any insights/advice? It’s by no means a deal-breaker but I’d like to have some idea of what to expect.
– A humble reader

As long as she doesn’t mind YOU drinking, enjoy it. It takes a little time to adjust to life without the social expectation of shared drunkenness, but the benefits are real: cheaper dates, all-time designated driver, and — should things ever progress to pregnancy — she doesn’t hate you for drinking while she can’t. Go forth and embrace her sobriety.


Bandwagon Seahawk Fan,
Hello good sir. Sorry about that bandwagon jab, just a joke.

A joke that would perhaps cut deeper if I hadn’t been writing about my Seahawks fandom since 2006 with articles that detailed my fandom throughout the ’80s and ’90s.

Sex: My only question is what do you miss most about being single? I only ask because I hope your wife still reads this every week.

I don’t think my wife would be shocked to learn that I think the best part of being single is the freedom to sleep with new and different people. But I wouldn’t say that I miss that, because I’m not a particularly nostalgic person. Meeting and wooing someone sexy is definitely exciting in a way that marriage isn’t, but it’s also laden with the frustrating bullshit of dating.

There are other freedoms to miss, of course: more time with your friends; more drunken stupidity; more time in athletic shorts and stained t-shirts, perhaps; more time playing video games if you’re into that. For me, none of it’s preferable to having a nicer home, cooking dinner and watching Netflix with the same funny person, and sleeping next to someone I love every night. I like the steadiness, even if it makes me less fun to hang out with by the standards of twentysomethings.

Fantasy: I know it’s super duper early but I’m trying to figure out my best course of action for my Keeper league. We get to keep 2 athletes, taking them two rounds later than drafted the prior year, and can keep a guy for 4 years max. Free agents picked up during the year cannot be kept. Here are the best options I have:

-Arian Foster, round 2
-Keenan Allen, round 11 (my only certain pick)
-Jordan Cameron, round 13
-Kenny Stills, round 14

Arian Foster is the only one that was drafted prior to last year so the latter three would have every year of “eligibility” in play.

I was leaning towards Keenan Allen & Kenny Stills prior to the draft, post draft I’m thinking Keenan Allen & Jordan Cameron. Depending on draft position (determined a week prior to our draft in August) Arian Foster could be in play but I’m wary of his prior workload, injury history, etc.
Help me Captain Caveman…. you’re my only hope.
-Lorne Malvo’s Barber

Nope, you’re right to go with Allen and Cameron.


Dead Capt Spaceman,
I am recently engaged, and am contemplating guest lists. I am marrying a girl from college (I am now 30) at our university cathedral. Most of the invites will be our mutual friends from college and the two towns we have lived in after college. I moved around a lot as a kid, but have stayed remotely close with a few friends from all over the country. I want them to be invited to my wedding, and I would love to see them, but I think it would but them in an awkward situation — they wouldn’t know many people, would be in a small, remote town (college is on top of a mountain in a 5,000 person town), so they wouldn’t have much else to do.

I know I won’t have much time to entertain them, so should I even bother inviting them. I don’t want them to feel compelled to come, but I don’t want them to feel slighted either. These were my best friends at some point, and I do keep in touch (text a few times a year, maybe see each other passing through on vacation). Ideally, I’d invite them, and they wouldn’t come, just so no feelings are hurt and I don’t feel nervous about entertaining.
So where do you stand on childhood friends?

Invite them. They’re adults who have the ability to meet new people and make small talk. Unless they’re total morons, they have an innate understanding that they don’t get to monopolize the bride and groom just because they don’t know other guests. They’ve been to weddings before, you know?

If they say yes, THEN you can tackle the problem of where to seat them. And while the seating chart can be one of the more difficult aspects of planning a wedding, it can also be fun to plot which sets of friends you think will get along. Then, as the wedding rolls into the night and you see your childhood friends drunkenly laughing it up with your intramural Quidditch teammates, you can think, “I AM A GENIUS OF SOCIAL INTERACTION.”


Note to readers: this final email was a single-paragraph, thousand-word block of text when I got it. When you read it, you’ll understand why.

Greetings captain,
Sex/relationship question: I apologize for the length but this is kind of a doozy, at least for me. I’ve never really had to deal with something quite on this level before, at least from a complication factor. I’m getting married soon. Like, next month soon. I could not be happier or more excited about it, and my fiancée and I are both tremendously in love and trust one another fully. I take a lot of pride in the trust aspect of that and believe it’s a sign of maturity and a strong relationship. However, she is the type of girl that guys just tend to fall in “love” with after meeting her for a short time. She’s very attractive and also INCREDIBLY personable, sweet and open to almost everyone she meets. On more than one occasion this has led to her having to explain to coworkers or guys she otherwise interacts with that no, she is not in fact interested in them, she’s just a nice person.

To be fair, sluts are nice people, too.

Your fiancée’s not a slut, of course; I’m just saying there’s room for confusion. For example: I’m very self-conscious about anything that could be seen as flirting with my co-workers, because I don’t want others to think of me as Pervy Married Guy. If your fiancée is constantly fending off admirers because she’s so nice to everyone, maybe she should consider dialing down the charm a little bit.

(In light of the #YesAllWomen conversation happening on Twitter, I want to make it VERY clear that I’m not faulting your fiancée’s actions at all. I’m merely pointing out that when we make a lifelong commitment to another person, we often need to re-examine our established behaviors.)

Again, I completely trust her and I think I do a very good job of politely reminding her on a regular basis that literally every guy she thinks is “sweet” wants to fuck her. She works in a very male dominant corporate job and I’ve met a lot of these guys. They are either sad techy “nice” guys or ultra-douche alpha dickheads.

Sounds like a blast.

I really wish that weren’t true, because it sounds like such a typical jealous boyfriend attitude, but sadly it has proven to be reality. Usually these scenarios revolve around dudes that we aren’t really friends with and it’s very easy to resolve. However, there is one guy at her office that I would consider us very close with. We used to hang out with he and his wife on a regular basis and I would have considered them very good friends.

Well, over the past few months this guy has been going through a divorce and having a hard time with it. My fiancée, being the ultra-supportive and wonderful person she is, is always trying to make him feel better. We’ve all gone out for drinks with him and stuff, and I actually did believe he was one of the rare guys that could be friends with my fiancée and I could trust.

Fast forward to last weekend. It was my bachelor party and my best man had done an awesome job and gotten us a beach house for a long weekend of partying. It was everything a bachelor party should be, and it was an awesome time. Before I left, my fiancée had specifically told me not to worry about her and to have an awesome time and she would talk with me when we got back. The last night of the party, I came home extremely inebriated and found an incredibly distressed text message from her saying she was so sorry to bother me but she needed to talk to me because things were not ok. Needless to say, this freaked me the fuck out. I managed to fight off my drunken haze enough to call her.

She basically explained that she and a group of work friends had gone out with this guy and all gotten drunk. They all then went back to his place to hang out and drink more. Now, she knows that this is a very precarious situation, but like I said, she’s extremely trusting. Anyway, as he gets drunker, he basically admits to my fiancée that he’s not quite as stand up a guy as we thought. He’s been cheating on his wife with TWO girls at their office that my fiancée is friends with and one of whom is fucking married and coming to our wedding.

Again, your lady’s corporation sounds really great.

He then proceeds to grab her and drag her back to his room and, not to be overly dramatic, basically attempts to rape her. She managed to get away and sneak out and that’s when she called and texted me. Sadly I didn’t have my phone on me because we were at the beach, so I didn’t see the messages until about an hour after this happened. As a guy, I’m fucking furious. Like, I don’t really know how to even control myself or react. This dude, who was supposed to be our friend, used the fact that I was out of town for my BACHELOR PARTY to try and pull this move. One of the worst parts is that she has to interact with him literally every single day at work and they are even sent on business trips together sometimes. This is not good. Not good at all.

Yeah, um, about that. Attempted rape is a crime. You should be talking to the police, not me.

Of course, he used the “I was so drunk I don’t remember anything” apology with her when he texted her the next day. Bullshit. I’ve been so drunk I don’t remember anything, and I’ve acted like an ass and regretted it the next day. 

Again: it was a crime. “Oh man, sorry about last night. I got so drunk I don’t remember anything! What? I murdered a guy? Oh well, I was drunk, what’re ya gonna do?” –> not a good legal defense

What he did clearly showed signs of premeditation. I am looking for any advice here at all on how to handle this. She did go into work and tell her boss (who’s also his boss) what happened. It just happened, and the fallout from it hasn’t even had time to occur at their office, but I’m struggling with whether I just never speak to him again and let him get fired or otherwise dealt with or whether I just follow my instinct and confront him. That seems like it has bad potential, but it also feels like I’m not doing anything if I don’t do it. Thoughts?
I’m so fucking mad from typing this I can’t be clever

If your fiancée’s corporation is worth its salt, the H.R. department has already intervened to the point where they’re no longer working together — although given its male-heavy environment, I wouldn’t count on them to do the right thing.

Unlike most people in every comments section, I’m not a lawyer. But if it were me in your shoes, I’d be talking to the cops and pressing charges, and if there wasn’t enough evidence to prosecute, then I’d be talking to lawyers about a civil lawsuit. Doing everything you can to destroy his life and livelihood will speak much more loudly than confronting him in person — and it will do a better job of preventing him from trying to sexually assault another woman.

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