Am I flirting?

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 wants your money and your sexy-bits, not just your money?

Gym Membership Guy isn’t in an enviable position. It’s hard for him to express the difference between his trying to get a girl to join the gym and trying to get her join him in bed. His very choice of job makes him untrustworthy.

You’re not in a great spot as the object of Gym Membership Guy’s interest, either. If you join the gym, he might think you’re flirting — even if you’re doing it for your abs, and not for his. If you don’t join, but you keep in contact with him, he might think you’re flirting, because you are.

Basically, this character is a sticky flirting-wicket, and any situation he’s part of becomes instantly complicated. If you really want him, you have to be lucky enough to encounter him outside of his job. Flirting is always better with more drinks and fewer conflicts of interest.

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 acceptable, but anticipated, regulated, and mandated by whatever cultural elite it is that still thinks Playboy is relevant to actual human beings’ sex drives.

No, it isn’t “flirting” to turn yourself out for ONE NIGHT ONLY like a goddamn promotional deal at Mattress Discounters. Which isn’t to deny the sex-having aura a short skirt, stockings, and garters can lend. But there’s nothing more awkward than a girl in her first platforms on October 31st. Unless you are going as yourself, Clumsy Slut. Which would still be sexier any other day of the year.

14. If I look fantastic in a suit, look fantastic in casual wear, look fantastic in ANYTHING, sound good, smell good … ?

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 — and it is, even if you haven’t seen Mad Men before — but Am I Flirting? would like to offer a look at the serious side of Draper’s advice.

Step 1: When in doubt, remain absolutely silent.

Although it’s a little counterintuitive, you can successfully flirt by saying nothing at all. This is great advice, actually, because in the age of yappy-ass bloggeurs, sometimes it’s refreshing to find someone who will shut up and pay attention to what you’re saying. A good listener, with body language that shows he’s listening, is playing in the big leagues of flirting.

Step 2: Be vague.

There’s something to be said for maintaining an air of mystery in the arena of flirting, but be careful with this one if you find yourself deep in relationship territory. It’s one thing not to talk about your family while you’re getting acquainted at a bar. When you’ve already moved in with a girl, and she still doesn’t know where you grew up? That’s just suspicious. Remember: everybody wants to sleep with Don Draper, but nobody wants to be married to him.

Step 3: Have a great name.

Even if your name is Nathaniel Schnirpus, you’re not doomed to a life of lackluster flirting. Introduce yourself with confidence, Nathaniel Schnirpus, and she’s not going to care about your name. Trust us. Alternately, for those of you with names that trip musically off a pretty girl’s tongue, don’t get complacent. “Don Draper is a DOUCHEBAG” has a musical ring to it, too.

Step 4: Be Don Draper.

Here, Draper gives a litany of the qualities that are essential to his character’s charm. If you have any of these, by all means use them. Remember, though, it’s enough to smell good, sound good and look fantastic in a suit. You don’t have to take the trouble to point it out, too. This bespeaks an insecurity that hardly qualifies as flirting. If you have ALL of these qualities, then put your computer away, leave the house, and bless the opposite sex with your irresistable charisma.

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 aren’t jacking it: you’re just having a regular conversation, one where you totally aren’t refreshing the top videos this week on fantasti.cc, you’re just remembering the last time you really did find a good free MFM threesome clip, and god, that’s so rare, and don’t you think? You ask, “I mean, why is that?” And in so doing you aren’t even necessarily revealing your actual personal taste in such things. You’re just making conversation — safely hinting even — about what turns you on.

Heaven forbid if every sexual topic of conversation is flirting: but having a “thoughtful” — or even thoughtful conversation about porn can played for flirt value. For anyone who’s seen too much (or made too much) porn, such banter is a way to bond over shared struggles: dear god, not another mislabeled, esoterically-edited ideepthroat scene! Making humor out of the badness and boredom of (some) porn can be a safe way to talk about sex with someone you barely know — hey, it’s just porn, it’s not like it’s about me. Yes, yes, oh whatever bad jokey porn music goes here yes, you’re flirting.

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, you’re saying “Hey, I’ve been checking you out,” without actually saying “Hey, I’ve been checking you out.”

This is nearly a foolproof flirt, but take heed of the following ways you can totally screw it up:

1) You can do it every day. “Did you do something different with your hair?” becomes a wee bit obsessive if you told her you liked her new earrings yesterday, and made a comment about her shoes the day before.

2) You can drag it on way too long. The more time you spend talking about her hair, the more you sound like Jimmy Stewart in Rear Window. Keep it short, and walk away while she’s still flattered.

11a. If I Ask Him About The Book He’s Reading On The Train? (addendum)

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 off as patronizing or ill-informed. So, what did the girl in our story do? She smiled, nodded, and got off at the next stop.

We reiterate: book-flirting is one of the most deeply satisfying forms of flirting, when it’s done right, and that’s a good reason to know your stuff.