• Mon, Jun 13 2011

The Editors Debate: Should You Ask A Man Out?


This morning, editors Jennifer Wright and Ashley Cardiff got an e-mail from a reader. The reader is a Florida-based student currently spending the summer in NYC. Every morning on the subway, she sees this one good looking guy. They’ve exchanged smiles a few times. Since she’s only here for the summer, she’s not looking for anything serious, but she would like to go on a date or two with this hot stranger. So, she asked us what to do. And we figured it out, obviously.

Jennifer: So. Should you ask a man out? I think this really depends upon the kind of relationship you want to have, and the extent to which you want to be the pursued one in the relationship. I don’t think it matters as much here as it would if it were going to be a long term relationship, but it’s still something to consider.

Ashley: You’re saying that if one is some kind of unsavory woman, she can go about tossing her number to men like so many coins or symbols of her willing genitalia.

Jennifer: Yes. Really, it depends on what you want. Do you want to be wooed? If that’s incredibly important to you, then I would say drop broad, obvious hints but wait for them to do the asking. I once pursued a man in some sort of soap opera manner – shaking my fist and silently declaring “you WILL be mine” and such. And we dated – and I don’t think we would have otherwise – but I never felt wooed the way I wanted to be. I don’t regret it, but the experience made me realize that I’d rather be the pursued than the pursuer. That’s just me, though! And I think it’s actually good to have some of each kind of relationship so you know what you do prefer.

Ashley: Sure. I think I’m too shy to initiate anything, honestly. One time I tried to ask someone out in college and it didn’t go over well because I’m a spaz. I blocked most of it out but I think I asked him about who his favorite Ninja Turtle was. Ugh. I would avoid initiating because I know I’d look like a jackass. I think there’s plenty of women who could pull it off. And really well.

Jennifer: So, Donatello? Because that’s fucked up.

Ashley: I mean, obviously Donatello. Raphael is cool but rude, Michelangelo’s a party dude and Leonardo is a boring asshole. And a gloryhound.

Jennifer: I actually meant Raphael. I’m sorry. I loved Donatello.

Ashley: Raphael had a temper and was brooding and sexy. In this way, he is an acceptable choice. But Donatello was smart and good-natured and he did machines.

Jennifer: He was the inventor! The mild mannered charmer of the group! WE’RE GETTING SIDETRACKED WE CAN’T DEBATE TURTLES PEOPLE NEED OUR ADVICE WE HAVE TO SAVE THEM LIKE THE TURTLES DID.

Ashley: I feel like you’re missing the forest through the trees. Let me put it this way: if you’re the kind of girl who loves Donatello, you want to be pursued in a smart, inventive, interesting manner and not an obvious or aggressive way. Donatello’s a gentleman but also an oddball. If you’re the kind of girl who loves Leonardo, you’ve got conventional tastes and you just want a guy to pursue you in a straight forward, dinner-and-a-movie kind of way. If you like Michelangelo, you want to go do something fun and spontaneous, like ride mechanical bulls on quaaludes. If you like Raphael, you’re down to fuck. You just want to fuck all the time. If you’re a Raphael girl, get his number. If you’re a Donatello girl, let him come to you. I’m saying it depends on what you want from this guy.

Jennifer: Riding mechanical bulls on quaaludes is my perfect date night.

Ashley: Then I think either of you could approach each other, because you’re both fun, easy-going, spontaneous people.

Jennifer: I like that we’ve managed to make this all about the woman and who she is and what she wants. Like, how important is it that a man/turtle send you a pizza launcher or other romantic gift sometime in your relationship? Would you care if he forgot the day you became a mutant? I would care very much!

Ashley: Donatello would be attuned to that because he’s sensitive and insightful. Leonardo will always remember significant dates because 1) he’s very traditional and 2) he has a secretary to do that for him. Raphael only cares about fucking you. Michelangelo has problems with short term memory.

Jennifer: I’d actually be a better match with Leonardo, wouldn’t I?

Ashley: Yes, absolutely. That goes without saying.

Jennifer: I want them to remember not because they care but because they’re bound by honor and force of habit. THE STUFF THAT LASTS.

Ashley: Leonardo would pull your chair out for you, Leonardo would impress your parents. He’s kind of the classic well-bred, well-mannered, privileged alpha male. Leonardo has little to offer but always remembering your birthday and endless nights of sober missionary sex.

Jennifer: I mean that sounds like… exactly what I’ve always enjoyed in relationships. You’d obviously always go for Donatello, yes?

Ashley: Yeah. It’s weird, I like Raphael’s aggressive masculinity as well as his anguish. I also like Michelangelo’s love of laughter and willingness to fail. But Donatello’s brain combined with his moral compass are my ideal.

Jennifer: I like that Leonardo will always remember to send flowers on my brithday and say the right things at the right time. I want someone who can just say “you make me happy” without following it up with “insofar as another human/turtle can ever MAKE anyone else happy.” The way Donatello always does!

Ashley: That’s because Donatello is a thinking individual and wouldn’t just lie to you for narrative’s sake. Donatello would respect me too much to say saccharine bullshit. The exact kind Leonardo trades in.

Jennifer: Oh, fuck you, he’ll never be in charge. He’ll always be weak. Hobbled by his own “philosophy.” I want a turtle of action. A leader.

Ashley: Fuck you. You’re going to marry that yachting chode with his unflinching smile and after you pump out 2.5 WASP-turtle hybrids, you’re going to stop by his office one night as a surprise to find him with his hands in the office fishtank. He’s never going to truly love you because he’s incapable of anything but self-love. He’s also fundamentally unimaginative. What I’m saying is Leonardo may be a go-getter, he may be extremely successful–though that’s easy when you and your strong jaw and firm amphibious handshake are given everything in life–but Leonardo is also a dead soul, empty at his core, nothing but a black hole of social unrest and mounting despair under two polo shirts with both collars popped. Fuck Leonardo.

Jennifer: I’m so excited to send the baby turtles to Choate!

Ashley: Donatello and I will be homeschooling ours.

Jennifer: They’ll be toilet trained when they’re READY to be toilet trained, goddammit!

Ashley: They’re quite good at expressing their feelings about toilet training, just not actually being toilet trained.

Jennifer: Mine will be afraid to poo, will hold it in for years. That’s what restraint IS.

Ashley: Gross. So. Should you approach a guy you’re attracted to on the subway?

Jennifer: Maybe. Should you?

Ashley: Depends.

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  • Vic

    I asked a guy out once by giving him my number on a sugar packet… does it matter that it was Imperial Sugar and not Splenda?

  • Eileen

    Choate >>>>> homeschooling. Just saying.

    • Jennifer Wright

      Also, have you seen their website? The Choate kids legitimately look like human turtle hybrids. The turts are going to have the best years of the lives there! I can’t wait to visit them to watch them just DOMINATE in water polo!

    • Ashley Cardiff

      As a homeschooler, I disagree.

    • Eileen

      Eww, you were homeschooled? I like you less now.

      Actually, I’m totally biased because all the people I know who went to Choate are really nice, cool, non-pretentious people and the homeschoolers are privileged hipster snobs. This probably isn’t indicative of the whole of either population.

    • Jennifer Wright

      No, Eileen, you are correct about everything.

    • Eileen

      Jen, I did suspect that – I usually am, after all – but it’s always nice to give the other side the benefit of the doubt.

  • Lisa

    I actually prefer to do the wooing, it’s not that hard. There’s suspense and stuff! I hope the girl asks the guy to hang out! It could be good.

  • August S.

    I tried to post a Dorothy Parker poem and my comment disappeared into the ether. This can only mean one thing: your server is being haunted by the ghost of Clare Boothe Luce. You should probably take care of that.

    PS: The poem was “Interview,” and I still think it is quite applicable to this debate, CLARE.

  • Alexander

    Might I suggest that the key point here is, it’s the SUBWAY? A decent or cautious man is likely to be reluctant to ask her out because (1) she might be scared or offended, and (2) she might resort to violence, or at least post his picture on Hollaback.

    Ordinarily, I’m for women dropping hints and men doing the asking. But in this context, if you want him, you’re going to have to make the first move — even if it’s just half a move, such as giving him your number and waiting for him to call and ask you out.