KSK Mailbag: How to Talk to Attractive Strangers

04.03.14 4 years ago 121 Comments


Hello friends. Apologies for the slightly-later-than-usual mailbag. My Wednesday night preparation was thrown off by the USA and Mexico playing a soccer game that started AFTER 11:00 p.m. on the East Coast. That perverse scheduling set off a series of dominoes in my life, the largest of which was “being hung over all day.”

Fortunately for you and me, a li’l hangover has never stopped me from writing TOP-TIER, SUPER-PREMIUM life advice. Let’s do this!

Hola Cap’n,
I know you hate baseball,

I don’t hate baseball at all. Baseball is fine, and I enjoy going to games occasionally. I don’t care for baseball supremacists or people who live-tweet the game they’re watching, but these are complaints about people, not the sport. Baseball as it is is a charming and endless endeavor. It is America’s cricket.

so I’ll ask a fantasy question: two keepers, standard 12 team league, lose the round you drafted the keeper in.

– Stafford (and hope he puts up video game numbers with now a #2 WR) for an 8th
– Megatron for a 1st
– Jimmy “Don’t Bend My Goalposts” Graham for a 3rd

People will yell and throw rotten vegetables at me for this, but I’d go with Stafford and Graham. While I happily admit the awesomeness of Calvin Johnson, he’s appropriately valued as a first-rounder — and if you end up with the first or second overall pick, he’s probably not the guy you’d want to use that pick on. Meanwhile, Jimmy Graham is typically gone by the second round, and Stafford is an excellent fantasy QB for an 8th-rounder. GO WITH VALUE, says I.

On to (too long and complicated) relationship stuff.

Obligatory background info: I’m 27, have Bachelors and a Masters degrees, and have a stable job that pays me to be solidly in the middle class. I was married at 21, divorced by 24, and have dated girls since.

The lesson: do not make important life decisions at age 21.

All of those girls were objectively pretty, so I know that I’m not ugly, but I’m not gonna model anytime soon either. Problem is, I have zero (and I do mean goose egg) amount of self confidence. This stems from childhood sexual abuse issues, and I’ve seen a therapist about these, but they still stick with every single day. Sometimes they take the form of flashbacks (as a military man, I’m almost positive you know these suck), anxiety attacks, and the aforementioned utter lack of self confidence. No matter where I am or what I’m doing, if I actually like a girl for more than wanting to hookup, I can’t pull the trigger to simply ask her to drinks or dinner.

I’ve been on the Ufford Approved Post Up Plan, even though there isn’t a breakup, and I just moved to a new city, so I’m actively trying to get involved in things that interest me in the community. I’ve really tried to work hard on not having a negative outlook on things, but my past (sexual abuse, had two miscarriages while married, divorce, etc) is really having an effect on how I perceive woman and relationships (or lack thereof). This is why things like Tinder are good, since I objectively know (for lack of a better word) that certain girls want to be flirted with/asked out/whatever else.

Going to my therapist was the best choice I ever made, and I could not stump harder for people to go and see one for any issues. But I still can’t manage to go up to a girl I like, with confidence, and ask her out for a drink. Any suggestions?

As a reward, Anna Kendrick is going to be on SNL, and she was already in GQ. Because she’s basically perfect.
First Time Caller, Long Time Listener


First of all: Anna Kendrick is a national treasure, and her DNA should be harvested so that future generations can clone her and appreciate her mix of talent, humor, and approachable sexiness.

As for your self-confidence issues, I won’t tread on your therapist’s territory, and I applaud your decision to get professional help for an awful thing that should happen to no child. This mailbag is a nice community for us to talk about shit, but we can’t compare to actual, professional help. So, good on you.

I will say this, though: having anxiety about approaching an attractive stranger is just about the most normal thing ever. The only solution for it that I’ve ever known is to genuinely not give a shit about the outcome of the interaction. Think about everything you’ve survived — “sexual abuse, had two miscarriages while married, divorce, etc” — and ask yourself: what do YOU care about one person saying no to hanging out with you? You’ve been through the SHIT, what’s a little rejection?

Oh, and that person you can’t just walk up to and ask out? She’s not some flawless goddess. She’s just a normal person who’s self-conscious about the weird mole on her back, or her teeth, or her belly button. Do you like the way she wears her hair? It’s to hide her ears, which she thinks stick out too far. Maybe she’s got an annoying laugh. Maybe she doesn’t like “Game of Thrones.” Maybe she’s a complete bore (this tends to be the case with very attractive people).

Here’s an anecdote (and one I’ve probably told before). Years ago, I saw a cute girl at Penn Station. We were obviously waiting for the same train, which was delayed 10 minutes, then 20, then an hour and 15. I said, “Hey I’m gonna get a drink while I wait, you wanna join me?” And she was hesitant, so I was like, “If you’d rather sit on your luggage for the next hour, suit yourself.” Because fuck her. I’m happy enough with who I am that I can get a drink by myself, you know? Anyway, she joined me for a drink, we started dating, and now she lives on in all my stories that include the words “the worst person I ever dated” and “just an awful human being.”

Anyway, the point of the story is we’re all just sentient meatsacks whose pointless lives don’t even last a cosmic eye blink. No human is too intimidating for conversation.


Dear KSK,
I’m getting married in a few months and lately I keep having dreams where I’m having sex with a girl who is not my future wife. I never had these dreams until recently and now they’re happening at least twice a week. The girl is usually someone different from dream to dream. Sometimes it’ll be one of my exes and other times someone I don’t recognize. In my dream, I’m always fully aware that I’m cheating on my fiancee and I always feel guilty. I don’t read into dreams, so I’m not worried about actually cheating, and I don’t feel guilty in real life. I’m just wondering if this is unique or if you and the readers have had recurring dreams like this leading up to a wedding as well?
-Fart Stupidton

That’s a good question, Fart, and now seems like a good time to remind readers that I make up fake names for submissions that aren’t signed.

Anyway, it’s totally normal. You’re normal. The whole point of sex dreams is having sex with people you can’t have sex with. Like, why would you have a sex dream about your fiancée? SHE’S LAYING RIGHT THERE. You can have actual sex with her whenever she wants.

Fun aside: I once dated someone who got mad at for something I did in her dream. Allow me to repeat that: her unconscious self concocted a version of me that did something wrong, then she woke up and was mad at me for a construct in her brain. This was the Penn Station girl. Never pick up strangers.


Hey Captain (no time for nicknames, I’m terribly busy),
Relationship shit first, and I’ll do my best to keep it succinct. Last year, I dated a girl (we’ll call her “Girl 1” because creating an alias for an already-anonymous story is idiotic)

I agree! Why give people human names when we can label them with numbers? It’s such a pointless part of storytelling, which is why my favorite characters in Top Gun are Pilot 2 and Navigator 1.

who broke things off because she wasn’t over an ex. We remained friends and occasionally hung out, though I was always loath to take another shot because I kinda didn’t buy her reason for ending things- I just assumed she wasn’t as into me as she’d originally thought and wanted to bow out gracefully. Whatever, shit happens.

Fast forward to a few months ago and I have a new girlfriend (henceforth known as “Girl 2”.) Everything was going fine- we got along well, she was great company, all that jazz. Then, last month, my brother died.

He had been dealing with heart issues (he was 32 and in phenomenal shape) but he was feeling much better and was optimistic about his recovery when we last spoke, so naturally it came as a huge and awful shock. While I was out in San Francisco with my family taking care of his affairs, I noticed that Girl 2 was really just getting on my nerves (pro tip: sending constant “How are you?” texts and GIFs to “make you smile” to someone in the middle of a massive life event who clearly needs some time and space isn’t a good idea.)

Oh God, that’s awful. How old is she? Twelve?

Meanwhile, Girl 1 was amazing: incredibly supportive, very patient and very understanding- she’d gone through the same thing with her sister when she was younger, so she has a much better grasp of what it’s like.

Why is everyone’s sibling dying young? It’s like you’re writing from Downton Abbey.

By the time I got back to New York, I was fed up with Girl 2 and broke things off, telling her that I couldn’t be in a relationship with anyone, which was true when I said it; HOWEVER, Girl 1 had me over for dinner the next night, we hung out more after that, one thing led to another, and we’re dating again. She’s been amazing throughout all this- I honestly have no idea how I’d be getting through this without her, and I’m extremely happy that we’re back together. Girl 2 and I haven’t talked much since the breakup, but she’s under the impression that A) I’m still single (I’ve done nothing to disabuse her of that notion since I didn’t want to look like I dumped her for my ex- I guess I made my bed on that one) and B) We’ll be resuming our relationship once I’m feeling ready to do so.

My question is twofold: since Girl 2 and I only dated briefly, am I obligated to tell her that I’ve found someone new and don’t want to date her again? And if so, how do you suggest doing it?
Thanks for the help,

You are under no such obligation. If you broke it off with her and have drifted out of touch, then she can figure things out from the standard social media stalking that every human now does.

If you’ve been texting her, do so less often and more tersely; you don’t need to say “I’m dating someone else” unless she asks you to hang out. Otherwise, initiating that conversation out of the blue might feel like you’re rubbing it in. “What’s up? Still single? NOT ME!”

Also: I am terribly sorry to hear about your brother. I will not share a GIF to make you smile at this time.



Those are solely for me to enjoy.


Fantasy First: I’ve been in a league with mostly the same core group of friends since the beginning of high school with a few of the spots rotating. Through college, we could always meet up back home before school started back up for a live draft and designate someone as the money guy and pay the winner on Christmas Break. Most of us graduated last spring though and are spread out throughout the country. We still did the league last year, but no money got exchanged due to this geographical issue and as a result things weren’t taken as seriously. Is there most efficient system for long-distance leagues to handle finances and make sure they are handled in an organized and timely manner?

Yeah, it’s called PayPal.

Sex: Just started law school in the fall and still figuring out how dating works within such a small community after getting used being a small fish in a big pond in undergrad. But I asked a girl out at the beginning of this semester and she turned me down and essentially said I was great and she knew she would have fun going out with me, but she was going through too many personal issues with school stress to get involved romantically with anyone (she also implied a bad breakup from last summer).

In undergrad, I had some success with girls but dealt more often than not dealt with rejection and developed a good perspective on it in that there is no point in getting hung up on someone who isn’t into you as there usually isn’t much you can do to change that. However, past rejections for me have usually just been straight “no’s”, “let’s be friends”, or girls leading me on because they like the attention without any intention of taking me seriously. Like I said, not much you can do to change their minds and you need to move on when those things happen. But I never had a, “It’s not you, it’s my issues right now” response before.

Is that just a response nice girls give to guys to make them feel better about getting turned down, or is it common for a girl to tell that to a guy she would go out with under better circumstances? If it’s the former, I wouldn’t have a problem getting past this girl. If it’s the latter, then I might try one more time with her in the fall as I do genuinely like her.
An overworked and undersexed law student

Ordinarily, I’d be pretty resolute in believing that she was merely giving a softer edge to your rejection. In most cases, “I’m going through some personal issues and can’t get involved with anyone” means “I will never be attracted to you. Your mere physical presence turns my stomach, and I’d rather listen to Ugly Kid Joe’s cover of “Cats in the Cradle” on repeat for six hours than hear your voice.” (Loose translation.)

I’m willing to admit, though, that law school is a weird environment populated by people with terrible judgment. I’ve encountered some law school weirdos who were like, “I can’t try to have sex with someone, I have to read up on tax law” — particularly during that brutal first year.

So why not? Ask her out again, and if she says she doesn’t want to get involved with anyone romantically, say, “Perfect! I’m just looking for something sexual.”

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