October 2008
27 posts
16. With the Gym Membership Guy?
You probably know this guy, dear readers. He is ripped, cut, and every other violent past participle that goes along with a great body. He’s the Gym Membership Guy, and he totally wants you.
Or does he? There’s a certain amount of flirting that goes along with his job, and he’s usually great at it. But when you he gives you a disarming, well-rehearsed line, how do you know he...
15. If I wear a 'slutty' Halloween costume?
There’s nothing “flirty” about the ritualistic donning of hooker gear by good girls. I know there’s dudeslut costumes, too, but they’re never that slutty, anyway, so yeah, I’m gonna say it: DOUBLE STANDARD. I don’t need to tell you how fucked it is, that there’s one day a year when dressing like you’re asking for it isn’t just socially...
WatchFig. 14: Don Draper’s Guide to Picking Up Women. Am I Flirting? is simply mad about Mad Men, but not everyone can be Don Draper.
14. If I look fantastic in a suit, look fantastic...
Absolutely. In case you didn’t get the reference, Saturday Night Live recently featured a short called Don Draper’s Guide to Picking Up Women, with Jon Hamm in his role as the dashing lead of Mad Men. Draper is known for his ability to fall into affairs so easily that it looks accidental, and in this SNL segment, he delivers four secrets to his success. This is supposed to be funny...
Like this video. Wow, he really actually goes down... →
13. If We Talk About Porn?
Were you masturbating? KIDDING. Together? This can happen, right? You’re on the phone or IM or texting or whatnot, and he just happens to interrupt your flow, and I mean, it’s just going to take a second to say, “Hey, yeah, I did torrent the new TV on the Radio on your recommendation, and THANKS!” so why take your hand off your bits while… you…?
Okay, so you...
12. If I Notice That She Changed Her Hair?
Are you kidding? Noticing things without being creepy is your flirt-bread and flirt-butter — or flirt-meat-and-potatoes, if you prefer. If you have a crush on someone you see almost every day, like a co-worker or a barista, you’re bound to notice things like haircuts, new highlights, and the shaving-off of beards. When you comment on these things, especially the subtle ones,...
11a. If I Ask Him About The Book He's Reading On...
A parable worth remembering, if you hope to be a successful literary flirt, is the story of the guy who tried to fake his way through a conversation about La Ciudad y Los Perros in incompetent Spanish. Discussing Vargas Llosa’s first novel with a cute native speaker in her own language is a bold move. At best, you’ll impress her with your willingness to try. At worst, you’ll come...
11. If I Ask Him About the Book He's Reading On...
Unless he’s grading you for credit, usually, yes [1]. And only do this if you’ve read the book. You’ll sound silly if he brings it up in bed later.
[1] And even if he is your TA, that doesn’t mean you also aren’t flirting.
10. If I Send Him Songs Via Email?
This is another reader question. We appreciate all of the questions, gewgaws and flirtations we’ve received so far!
The exchange of music is an age-old prelude to the exchange of fluids. It’s a ritual that dates back even further than the time of Young John Cusack and his heroic boombox serenade in Say Anything. Although that was a landmark moment in flirting history, sending a song...
9. If I Twitter About a Cute Barista?
Another from the mailbag. The thing is, when you Twitter about a cute girl in front of you, you know she isn’t on Twitter at that exact moment to read it. (Even if you do have an iPhone and live in the Mission or Williamsburg or whatever it is and kids today etc. etc. etc.) What you’re doing is, to abuse post-structuralist theorists Judith Butler and Eve Sedgwick, performing a...
8. If I Point Out The Nude-Caterpillar-Like...
This is our first reader question, and, although we suspect our fair reader already knows the answer in his or her heart of hearts, we will attempt to fully address its nuances.
This scenario falls right on the line between clumsy flirtation — maybe you read one of those asinine pickup artist manuals, and you were using the boogie-splosion to score a “neg?” — and utter...
WatchFig. 7: Bringing your girl to R. Kelly greatly increases the likelihood that some flirting is going to take place. (Note to R.: if you’re reading this and you have questions about whether you’re flirting or not, we’ll just let you assume “yes.”)
7. If I Wink My Eye and Let Her Know I Got The...
Yes. [Source: R. Kelly.]
If I Write In With A Question?
If you urgently need to know whether something is flirting, feel free to write in with a question. Will we assume you’re flirting with us? Only if you want us to.
6. If I Bend Over?
I was watching this couple at a cafe, both leaning over the counter after ordering. And they looked so comfortable, bent over: bottoms out, sure, but it wasn’t a come-on at all. They were pair-bonded in their ass display. For all the socially reasonable moments when one can bend over, though — oh, let me get the check! you forgot your umbrella! is my ass falling out of this summer...
5. If I Mention Woody Allen?
You know what you are? You’re God’s answer to Job, y’know? You would have ended all argument between them. I mean, He would have pointed to you and said, y’know, “I do a lot of terrible things, but I can still make one of these.” You know? And then Job would have said, “Eh. Yeah, well, you win.”
If you name-drop the man who delivered those...
4. If I Tag Her In the Facebook Photos of People I...
You got home from the party. You’re too “awake” (drunk) to pass out yet, so you go sign into Facebook and see what other parties she’s ignored you at? Stop. If she hasn’t already approved those photo tags, it’s because she hates the photos or the people who took them or the visions evoked by her inbox alerts, of swaggering young lads who just go and rub one out...
3. If I Say Goodnight to Him on IM?
What is he now, your own little stuffed tiger to hold at bedtime? It’s definitely cute — and pleasantly noncommittal, hundreds of miles away from one another as you may be. But why are you small-talking at all? Flirting is a time to be sharp. Unless your idea of flirting with a daily “good night” is to pre-emptively stray into comfy relationshippy patter. And you...
2. If I Comment on Each of Her Flickr Photos?
This is in clear “yes” territory. Yes, you are flirting. No, she will not go out with you. (Have you even asked?) How is that shot of her $300 haircut supposed to be special if you also comment on, for example, the photo of what she had for dinner? This is the Internet equivalent of driving by her house every hour in your white van to make sure that she is safe.
1. If I Favorite Her Tweet?
We need a better word than Tweet. But sure, you are probably flirting if you know that she checks Favrd even before having morning sex. She may also be Merlin Mann.