KSK Mailbag: Where to Live in America if You’re Young and Single

01.10.13 5 years ago 243 Comments

There are plenty of questions in today’s mailbag that address the NFL playoffs, fantasy football, and various sex and love problems. But the comments below are going to be dominated by the last question: what American city would you recommend to someone who’s young and single. As someone who was single over much of the country, I have some opinions, and there’s nothing that people on the internet hate more than opinions. So enjoy. I look forward to your scorn.

Dear Matt,
Football: I don’t have a football question. Here is a picture of Jennifer Lawrence instead.

She’ll do.

Relationships: I admit this is stretching the purposes of the mailbag a bit, but I think you can help. My brother-in-law is getting deployed for a tour of Afghanistan within the next month. It’s his third tour (2 in Iraq already), but first since he started dating and subsequently married my sister.

I really like the guy, but as a result of living quite far apart I don’t know him particularly well. We’ve just not had a chance to get to know each other really well. He’s also a bit gruff on the outside and not one for sentimentality.

Do you have any advice for how to let him know I want him to be safe and come home OK? I don’t want to sound like Constable Bob with a “Stay frosty out there” having not been in the military myself.

A simple “Come home safe” is sufficient. “Keep your head down” is also an acceptable, non-douchey version of “stay frosty,” and if you want to dabble in gallows humor: “Don’t get your balls shot off, my sister wants kids.”

Also, what kind of things should I do for my sister? Do I bring up the fact her husband is in a war zone and get her worried? I don’t want to not mention it and look insensitive, or have it become an elephant in the room. (She’s in paramedic school right now, so she’s doubly stressed). As you can see, I’ve perhaps over-thought this a bit. What has worked in your experience?

I’m gonna go out on a limb and wager that she’s not going to forget that her husband’s in a war zone. “Whoa, IRAQ!?!? Shit. I just thought he was taking a really long time to get cigarettes.”

All you need to do is be there for her more than you usually would. She’s likely going to be lonely at night, so call her regularly just to say hello and see how she’s doing. Tell her about what’s going on in your life; it will help take her mind off of hers. And yes: ask how your brother-in-law’s doing. It will show her that you care about him, too.


(This question is from last week, but it asks about the Seahawks, so hey: still good.)

Hello Captain!
Since fantasy football is over, I figure I’d ask your opinion on the actual playoffs. Obviously my Jets are a molten dumpster fire of disappointment, so I thought I’d pin my hopes on your Seahawks for a decent run. The defense is dirty, I loved Russell Wilson at Wisconsin, and BEEF MOE continues to get his Skittles. I think they can pick off the Skins in DC, and I don’t hate a potential matchup against the Falcons, assuming the Packers rebound against the Vikes. How deep do you think they can go?

I also like the matchup against Atlanta — at least compared to an away game against San Francisco or Green Bay — but I think this game could be more problematic for Seattle than people suspect. A 1:00 start time on the East Coast for a West Coast team is a big handicap to overcome in an away game, and story lines that gets repeated ad nauseam in the NFL (“Falcons can’t get it done in the playoffs”) have a tendency to get blown up in due time — remember when Peyton Manning couldn’t win the big one?

Anyway, I think the Seahawks could be a Super Bowl team, but I think ANY of the remaining teams could be a Super Bowl team if the chips fall the right way. Except the Ravens. Flacco sucks.

Sexytime: A friend of mine sent me a link to a really funny blog post about a month ago and it turns out that the writer of the article is this drop-dead gorgeous girl about my age.

I’ll call her Kristen, since fake names are hard.

I went through some of her older posts and it as happens I really like [Kristen’s] work. I’ve occasionally gone back to the site for updates, but I hadn’t really given her or the blog much thought. Then last week I see a photo of a vaguely familiar person pop up in a friend’s photo in my newsfeed; turns out [Kristen] is living in Boston with a girl that I was friends with in college.

I will call your college friend Sarah.

My first reaction was: You should reach out to her! After all, the chances of us having a mutual friend is hilariously small and what do you have to lose? I thought about messaging [Sarah] on facebook and saying something like, “Hey! I’ve been reading this blog, I think [Kristen] is really funny and smart and pretty and oh, wouldn’t you know it? I just realized she’s your roommate. I was planning a trip up to Boston with some friends anyway (I live in Jersey) and I’d like to catch up with you and maybe buy your friend a cup of coffee if she’s interested. If not, no big deal.”

Not the worst plan, but not a good one, either.

Of course the more I think about it, the more it seems like a bad idea. I haven’t talked to my college friend in like 4 years (we weren’t really all that close to begin with), and I wouldn’t have thought about reaching out to her during the Boston trip if I wasn’t a fan of her roommate’s work. Besides, the whole thing could seem a tad creepy. “Hey tangential friend I haven’t spoken to in half a decade! I recognized your roommate from a blog that I occasionally read. She is pretty and I’d like to meet her during a road trip to your town.” Am I wearing bad idea jeans? How would you take that if you were in her shoes? I figure your line of work would lend particularly good insight to the situation.
Fireman Ed

Some people are going to disagree with me here, but I think that the best thing to do is comment directly on the photo. “Whoa, you know Kristen from FunnyKristen.blogspot.com?” Rather than using a Facebook message to start mapping out a road trip and hanging out for coffee, it’s a simple question that starts a conversation. You force an e-introduction of sorts. Sarah says yes, it’s her roommate, and Kristen gets flattered that someone is reading and likes her blog. That’s not creepy; it’s coincidence.

Once you’ve broken that communication barrier, you can say, “Well I’m going to be in Boston soon, let me buy you girls a round of drinks if you’re not busy. Sarah, it’d be great to catch up; Kristen, thanks for the laughs on your blog.” It’s still not seamless, but it’s better than showing all your cards at once.


Lady emailer!

Dear KSK,
I’m a senior in college who, after my first semester, never really settled down. I saw a few dudes, had my fair share of random hook ups, but kind of was really pretty damn single up until this fall. All of the sudden, I realized I had feelings for one of my really good friends. One of those “when you least expect it” moments, I suppose, as I found out it was mutual.

We started “seeing each other” (whatever that means)

“Fucking,” I would guess.

and he brought up that things could get tricky and complicated as he is doing long term graduate school and I have yet to get a job offer, but have been interviewing for positions in different states and even regions of the country. I mentioned something about just wanting to “live in the moment” and he realized that was the way to go. This is fun and there is no reason to stop having fun because my future at the moment is really, really vague.

However, now that we are at the stage where he introduces me as his girlfriend, or whatever, I find myself in the shoes he was in previously — unable to live in the moment.

This got really long and I’m trying to remember what my actual question of this was, but I suppose I was looking more for advice from a dude about how to handle a situation that is looking likely to have a deadline.
Thanks for any XY insight,
Stuck in the future

Oy, college kids.

So, the problem, as I see it, is that you’re in a relationship with fuzzy boundaries and a potential end-date looming. My guess is that this was okay with you until he started calling you his girlfriend, which triggered feelings/questions/worries about that possible end date that you were previously able to ignore by not thinking about it.

When you start over-thinking or worrying about something, the best thing you can do is break it down to its simplest elements: do the two of you enjoy fucking each other and not fucking anyone else? If the answer is yes, continue your relationship and don’t worry about bullshit words like “girlfriend” or “living in the moment.”

Conversely, if you’re not in love and not interested in a long-distance relationship with this person after graduation, then maybe you’d be happier being single and playing the field during your final months of college. Playing the field before you graduate is a fun thing to do that I did not do because I was dumb and didn’t have an awesome football blog to write to for advice. Blogs weren’t even a thing when I was in college, and people who used cell phones on campus were total rich snobs. I’m super-old.


My wife and I agree that simultaneous orgasms are the best. But we rarely get to experience them. She gets off on clitoral stimulation combined with slow, methodical thrusts. I find I need to play a little more fast and loose to come. Do you have any suggestions?

The best sex in the world is probably some tantric marathon on a swing over rubber sheets with lots of prostate stimulation and eye contact, but hey, that’s probably not on the docket for most of us. Sure, simultaneous orgasms are great, but I think the real key is that you BOTH are having orgasms, period. But if you really need to have them at the same time, try mutual masturbation. That can be plenty fun, and timing doesn’t get much easier.

Thanks to a midseason trade, I have two first-round picks for one keeper spot. Do I keep Calvin Johnson or Rob Gronkowski? I like Megatron, but the gap between Gronk and the rest of the TEs has me reconsidering. Standard scoring, 10 team league.
–At The Same Damn Time

It depends. Does your keeper cost you a first-round pick? If so, then I’d keep Johnson. As good as Gronkowski is, I still don’t think I want to use a first-rounder on a tight end when he could be available in the second.

However, if your keeper doesn’t cost you a first-rounder, I’d go with Gronkowski. In a ten-team league, there are enough outstanding wide receivers to give you depth and production at the position. But the drop-off between Gronk and the next tight end is significant enough to give you a decided advantage in a smaller league.


Zup Uff:
None of my friends like this idea, but I think that says more about their lack of creativity than anything else: Instead of a tradition FFL league that peters out before the season even ends, what do you think of a league where the regular season is game 1 through game 17, and the playoffs continue on to the Super Bowl, just like the Good Lord intended. Instead of an head-to-head elimination tournament, all of the points scored by every playoff-eligible player in your starting lineup is added up throughout the entire NFL playoffs, and the team with the most points after the Big Game wins (obviously). Even if you have Tom Brady or Peyton Manning, they could be one-and-done while some guy like Russell Wilson is lighting it up week after week. It also adds a whole ‘nother wrinkle to drafting, by giving Aaron Rodgers and Arian Foster a large advantage, and screwing over reasonable folks who thought the Steelers and Saints would move on rather than the Colts and Vikings. For those poor souls ho aren’t lucky enough to be Seahawks fans like you and me, it gives them a little extra football to enjoy before the dreaded Spring returns. What do you think?

I hate it. Your friends may lack creativity, but the presence of creativity does not mean it’s a good idea. Before the Wright brothers came along, people jumped off the Eiffel with wings attached to their arms.

At its best, fantasy football attempts to isolate and quantify players’ statistics in order to make fantasy owners feel like actual NFL GMs. That’s the heart of its appeal: the feeling of being a coach/GM. It’s why most leagues play head-to-head matchups even though points accumulated is a better metric to determine the best fantasy owner.

And you want to continue the fantasy season into the mess of Week 17 and the playoffs, why? So you can get your fix for a couple extra weeks? The only thing your plan does is introduce a greater impact for luck and variance. It would make every year a disastrous screwjob.

Furthermore, this all overlooks the most obvious point: the best part of fantasy football is that it makes games we otherwise don’t care about suddenly relevant. If you need an extra reason to care about the NFL playoffs, you’re either not much of a fan or a gambling addict.

As for sex, the less said the better. So here’s this:

Joey Joe Joe Junior Shabadoo

That almost makes up for your harebrained scheme. Almost.


Dear KSK,
Have a question for you that doesn’t really fall under the sex category, but hoping you can help me out. I’m a Canadian currently in my last year of university here. I’ve also got American citizenship through my parents so I’m looking at making the move down to the states once I become a free agent. All things being equal in terms of employment, if you were in your early twenties and single where would you go? Would I be crazy to put Seattle high on my list (coastal city, legal weed, Seahawks, basketball’s coming back)?

Seattle is an excellent city, and as a Canadian you’re less likely to mind the dreary, gray, wet winters where the sun is rarely more than a vague source of light behind the clouds. The summers are goddamn beautiful, though.

Every asshole thinks that where they live is the best place on earth, but what they don’t understand is that it’s the best damn place for them. I’m awfully happy living in Brooklyn and working in Manhattan, but I wouldn’t recommend it to anyone who wants a yard for their kids. So figure out what you want: if you like skiing or snowboarding, move to Boulder (this will also fit well with your taste for weed). If you want a major urban area that’s relatively close to Toronto, Chicago’s great. If you want hot weather and dumb hot girls: Phoenix or Tampa.

You can be happy anywhere as long as your interests match what the locale offers. Here’s the shortest possible guide of remaining American cities that I can make for the young, single, college-educated man:

  • New York — PROS: exciting; great food and art; tons of beautiful, stylish, smart women; no need for a car | CONS: expensive; awful real estate situation; dirty; no easy getaways to nature
  • San Francisco — Similar to New York, but with better weather and more relaxed people. Rent is just as expensive but you need a car as well. Aggressive hobos. Locals prone to smelling their own farts. Beautiful city close to beautiful places.
  • Chicago — Similar to New York, except it’s twenty degrees colder in the winter and strangers will make small talk with you. Fantastic architecture. Nothing good nearby unless you like cornfields or dairy farms (don’t give me that lake house shit, Midwesterners).
  • Los Angeles — Sunny. Beautiful women. I hated L.A. when I was younger because I thought that everyone was shallow (and because I hate traffic), but I’ve found pockets that I really enjoy as I’ve visited it more. If you’re well-connected and/or rich, L.A. is great.
  • San Diego — Like L.A., but without aspirations. Perfect weather. Unrivaled fish tacos. Just a really wonderful place to be young and single. The rare place where not having a job isn’t a big deal.
  • Dallas — Like L.A., minus Hollywood. Which is to say: pretty women and shitty traffic.
  • New Orleans — There’s a quote I always see that gets attributed to Mark Twain but I’ve never been able to confirm is by him: “In America, there is New York, San Francisco, and New Orleans. Everywhere else is Cleveland.” New Orleans has its share of problems, but the culture of the city is unrivaled in America: amazing music, unique food, a lively art community, constant trouble for a young person to get into. If you can handle the humid assault of summer, you’d do well to live here.
  • Cleveland — No.
  • Anywere else in Ohio — No.
  • Austin — The blue island in a very red state. Fantastic place for food and attractive women.
  • Portland — Kind of a cross between Austin (for weirdness/innovation) and Seattle (for mentality/weather).
  • Miami — Live here if you have a nice car and like Hispanic women.
  • Charlotte — A good place to be if you like barbecue, southern women, and NASCAR.
  • Atlanta — Too hot and humid for me, but there’s enough good food, music, and general weirdness in Midtown and Little Five Points to make me think twice if I were young and single.
  • St. Louis — No.
  • Denver — Nice, but you’re better off in Boulder.
  • Washington, D.C. — I know tons of people who love D.C., but man, it’s not the place for me. At its heart, the city is powered by government employees and politics, so while there’s some great international flavor, if you’re young and single you never fully escape from the politico-bots: guys in khakis and blue blazers with the same floppy haircut, and blandly attractive blonde girls who are looking over your shoulder for someone better-connected.
  • Nashville — Southern belles and quality music. Otherwise: no.
  • Louisville — BOURBON! There is an excitement to Louisville that you won’t find in a lot of the South, and much of that stems from bourbon and the Kentucky Derby. However, I went out a lot in Louisville when I was 22 and gainfully employed, and I was never terribly impressed with the singles scene. I am sure people who live in Louisville will shout at me for this.
  • Boston — A great place to live if you like Boston sports teams. If not, don’t live here.
  • Philadelphia — Less annoying than Boston with the sports. Similar to NYC in that there are pockets of influence from New Jersey, but otherwise fine, I guess?
  • Salt Lake City — PROS: close to Park City and fantastic skiing; lots of attractive people; an excellent launching pad for exploring the beauty of the American West | CONS: Mormons don’t put out
  • Tucson — PROS: Another outdoorsy city that gives you good access to the West. Attractive women. Not as hot as Phoenix. | CONS: Arizona’s batshit, dude.

Obviously, I’ve left places off that people will rage about in the comments (I see you and your shitty traffic, Houston), and naturally my opinions are just that, but in general, if you were just a random person I didn’t know anything about except that you were young and single and looking to have fun, I’d recommend San Diego. Go live on the beach, man.

In light of the unsexiness of this question, I’ve attached this Katherine Webb picture (controversy aside, my god this woman is attractive).

Keep on rockin In the free world,
Disgruntled Leafs Fan

Tuscaloosa! How did I leave Tuscaloosa off my list?

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