Derek Jeter | MISS WINGMAN

What’s better than scoring a date with a woman? Getting her back to your place for the first time. Well actually, scoring a relationship with her would be better, but we’ll start out slowly. Baby steps.

So you’ve managed to lure her back to your lair with your smooth-talking ways, or better yet, your genuine honesty and likeable personality. But no matter – she’s there – good job. What you might not have realized is that as soon as a woman walks into your domicile, she immediately does a visual scan of the premises.

What is she looking for? Anything to give her further insight into who you are – for better or for worse. This is your chance to make a winning impression – or totally blow it – depending on the circumstances. So, a list is in order to break down the good, the bad and the you-should-probably-hide-that of what she’s thinking when analyzing your bedroom:

Cleanliness: The first thing she’ll ask herself – Is it messy? Don’t worry, most guys are messy. We can handle it. But is it reeeeeally messy? Like, she’ll be wondering if someone from Hoarders lives there messy? Oh dear, this is a problem. There’s a difference between clothes strewn about and mold growing on half-eaten snacks stuck to plates. If you can’t be bothered to at least clean up a bit before having company, we may not be inclined to visit twice.

Framed Pictures: This one’s a no-brainer. Pictures of your family? Good. Very good. Pictures of your ex? Check please! Pictures of you with your friends? This is favorable, just make sure you’re not doing anything horrifying in them. Oh, and if you have pictures of you holding babies, with children or doing anything volunteer-related, she may just sleep with you right then and there. We’re suckers for that stuff.

Bed linens: I think this one is better illustrated in photos. If you own this:

Or even this:

…if she’s like me, she’ll laugh. I think any guy who would own this is hysterical, and pretty awesome for what it’s worth. But that’s just me, and I definitely don’t represent the whole female population on that one sadly. Would I sleep with someone who owned these sheets? Probably not. And I think I DO speak for all women on that point, sorry guys.

Maybe it’s because we expect anyone who owns these sheets to also own a race car bed, a la Rick Schroder on Silver Spoons, but in general you should keep the nostalgia to a minimum.

And speaking of nostalgia…Trophies/Awards: These are great if they’re relatively recent or just for something really impressive. If your baseball team were state champions three years in a row and you were the pitcher – even in high school – it’s still a pretty big deal. College and post-college achievements would be preferable, though.

Kindly avoid displaying things like your Perfect Attendance award from tenth grade or even your Cleanest Desk on the Sales Floor ribbon that the nice people in your office gave you last year. Award displays in general walk a fine line between being proud and narcissistic, just be careful which side of the line you’re on.

Visible Signs of Other Women: If we see any vestige of other females in your bedroom, it’s lights out – and not in a good way. Whether it’s finding discarded underthings from last week’s fling to spotting…other things (I will not elaborate, you get it), this is usually our cue to leave. Lipstick on your pillow, a number scrawled on your desk, these also fall into the same category: Thanks for playing, adios.

Speaking of women, if we spot things that are Obvious Ploys to Impress Us: rows upon rows of sneakers lined up like you’re a one-man Nike factory, a guitar that just so happens to be laying on your bed (and then you launch into a Mayer-style unplugged concert), expensive watches on display, etc., don’t think we don’t know what you’re doing there. Humility is a good thing – remember that.

And finally, your Wall Accents speak volumes. My general feeling is that men shouldn’t own posters – strike that, no one should own posters – after college. Unless you’re an extreme sports enthusiast and it’s of some snowboarder mid-insane air in some jaw-dropping stunt, it’s hard to justify. Sports are pretty much the only type of poster women would tolerate, if that. But if you display any images of scantily-clad girls, Pink Floyd album covers or Scarface imagery, you’ll probably be sleeping alone. We don’t require you to be sophisticated with your artwork (bonus points if you are!), but having a room that looks like it was decorated by Tucker Max won’t work in your favor, either.

That’s about it in terms of your boudoir, boys. I don’t want you to think that we’re constantly judging you (even though some women ARE constantly judging you), I’m just urging you to consider what impression of yourself you’re giving off to the world. No one says you have to live in Derek Jeter’s digs, just be a gentleman if you find yourself with female company. And please, whatever you do, don’t forget to make your bed.

The holidays are a time for reflecting. But what if, while looking back, there’s a figure in your rear view mirror that your current passenger isn’t too thrilled to hear about? When it comes to exes, there’s a fine line to put us at ease about how you regard her; Too fondly may mean you two still talk often (or hang out – which doesn’t sit well with most women). But, if you never mention your past, you may have us wondering if your love ended with a restraining order, or if she’s currently at the bottom of a river somewhere? No one’s so detached that you move on and nary breathe a word, after all.

Whatever your status with your former flame, there are a few things that your current (or potential) love interest will be none too pleased to learn about the One That Came Before. Just like most men don’t want to hear that our ex is the heir to a (fill in the blank) fortune with McConaughey’s good looks, Gosling’s sensitivity and the anatomical endowments of Wahlberg in “Boogie Nights,” there are certain things we hate to hear, too. So if your ex fits the following bill, perhaps it’s best to play your cards close to your chest:

A Model of Any Kind: Whether her bod graced the pages of an LL Bean catalog or, God help us all, a Victoria’s Secret glossy, why not do us a favor and keep that your little secret, too? Normally I’d tell you to always be up front, never lie by omission, but in this case that news may just mess with her head more than any normal woman can handle. No matter how confident a female is, we almost always compare ourselves to our peers. And, if you inform her that her peers now include genetically gifted chicks who don lingerie for a living, her head may just explode. Seriously, how would you feel if we told you we used to sleep with a Ryan Reynolds look-alike (or worse, the real thing)? Mum’s the word, boys.

A Do-Gooder: Does your ex volunteer for the Peace Corps? Is she healing the world one under-developed country at a time in Doctors Without Borders? Does she rescue orphans from war-torn regions? Yeah, this is a little too Angelina Jolie for your average woman to handle. It’s one thing to volunteer her time on a relatively local level – many of us do that, and enjoy it immensely – but if she’s off globetrotting or started her own Nonprofit, those are some big shoes to fill. We should all do good just for the sake of doing good, but that bar is set pretty high, don’t ya think?

She Lived With You (or worse, you two were engaged): No one takes a relationship to that level unless you’re really serious with that person. People break up and move on every day, but there’s something about the permanence this once showed that makes it hard for the one who’s with you now to ever feel like she’ll be as much of a presence in your life. Sad but true, and tricky to work around.

A Semi-Pro, Pro or Otherwise-Gifted Athlete: Two words, David Beckham. OK fine, maybe that’s not a fair comparison…But seriously, girls who have skills on the field or on the court are a tough act to follow – even if her name isn’t Hope Solo or Maria Sharapova. And being a female who’s good at something sports-related is about as good as it gets (unless she’s built like a Williams sister or is gender ambiguous, a la Beijing Olympics – not hot).

Granted, we know we shouldn’t worry about making such comparisons, but would you like it if she told you Once upon a time she dated Derek Jeter or Mark Sanchez? Or C.J. Wilson, or Cam Newton (I could go on and on here boys…) Right, didn’t think so.

Bi-Sexual or just Bi-Curious: We’re aware of your fantasy to see us with another girl, but if your ex actually WAS with another girl, that’s not just dipping our big toe in to test the same-sex waters, that’s diving head first into the deep end of the pool. I’m all for people being with whomever makes them happy, male or female, but that little tidbit may just make her feel like she’d never be seen as adventurous enough to entertain you in bed.

An Identical Twin: You boys and your fantasies again… We know, twins are twice the fun. So, even if you only dated one half of that novelty pair, at some point you still swam in the Doublemint Commercial pond, and probably liked it. Nothing we can do about this one, but still not terribly reassuring.

An Adrenaline-Junkie: Was she A) a pilot, B) a race car driver, C) an extreme sports enthusiast (read: she loved skydiving, motorcycle riding or snowboarding half-pipes) or D) a crack shot with a firearm? If so, we will immediately begin to wonder why you are now dating a regulation female like us. Even if your ex’s adventurous ways were too much for you to handle, it’ll still be hard to hear that you once shared a bed with a badass.

A Singer or Actress: This one is less “actress,” since the definition of that word is shamefully loose these days, and more “someone in the public eye.” If your ex had Adele’s pipes or used-to-be-on-that-television-show-about-that-guy, those types of run-ins are hard to avoid. Even if you swear that you’ve learned to resist her siren song, your current beau might not believe you. And she might have to stop watching TV or listening to the radio, too. Would you like it if our ex was a triple threat, of the Timberlake variety? No one would, hell I’ve known straight males who crush hard on that guy. But you get the idea.

Granted, in a perfect world your relationship record would be expunged, and we would all forget that anyone came before us. Women – and men, for that matter – prefer to feel like they were the first pioneers to, er…explore your land. But that’s not realistic.

Don’t ever lie about your past, lest you seem like you’re making a bigger deal out of something that wasn’t. Just realize that, once you’ve told us your ex fits into one of these categories, it might take us a minute to process the news. Then, it’s out there and you should answer any questions she has about it, but don’t dwell on it – move on as quickly as possible.

Making the one you’re with feel like she’s the only one that matters is important, but it’s also a two-way street. If you reassure her and she’s still stuck on it, or can’t shake her insecurities, then you’re dealing with a much larger problem. The confident woman will always prevail…just as long as your ex’s name isn’t Giselle.

MISS WINGMAN

Female musings for the modern man.

Tag Archives: Derek Jeter

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