I Hate to be the Wearer of Bad News…

You all remember Raul?  If not…by way of refresher, he’s a guy I dated – it didn’t work out, and I wrote a blog post about our “break-up.”  You can check it out here.

Well, Raul and I have remained friends and it’s a great friendship!  I asked him for advice, the other day, on what to wear for a date this weekend, and he sent me a mini tome on the matter.  So, naturally – I thought I’d post it.

I figured, the women can read it to get some insight into what guys think about how they prepare for and look on dates, and guys can read it to see if it’s an accurate representation.   I’d love some commentary below… I mean…do you other guys REALLY agree that you want a girl to come out “UN-spanxed??”  Can it BE?  I’m a doubting, spanx-wearing Thomas…
Convert me.


I have no idea if what I’m saying is worthwhile or representative of most guys – it’s just my sole opinion, but I’ll generalize as if I’m speaking on behalf of the entire US male population.

OK, here’s the bottom line:  99% of the time, we couldn’t care less what you wear.  Really, it doesn’t matter.  Whether you’re wearing a miniskirt or a canvas sack, we probably think it would look best on our bedroom floor.  There you go.  Plus, we won’t remember it the next day, anyhow, unless the impression was a really bad one.  How do you avoid a bad choice?  Follow these guidelines:

  1. Wear something appropriate.  This is the number one – and probably the only – consideration.  Fortunately, it is also the easiest.  We certainly don’t expect you to obsess over what you wear to meet us; using your normal judgment in what’s appropriate should be simple enough.  After all, we’ll hardly give a moment’s notice to what you’re wearing unless it’s totally, wildly inappropriate.  If we ask you out to a honky-tonk dive bar, don’t show up in a ball gown.  If we ask you out to a nice French restaurant, don’t show up in sweatpants.  This isn’t rocket science.  But it IS probably the only time we’ll make a judgment about YOU based on your clothing.  If you show up in blue jeans and a t-shirt for the symphony, we’re embarrassed.  We make certain assumptions about your background/upbringing/education, and will give serious thought before inviting you to something nice again.This also includes activity-appropriate clothing if the date involves a fair amount of movement (dancing, bowling, batting cage, shark wrestling, etc.), wear something that allows you to do that activity comfortably – if you knew what the date involved, we don’t want to hear you say “I can’t because my skirt is too tight / dress is too long.”
  2. Wear something you are comfortable in.  This means two things:  First, don’t wear something that will cause you to complain (I’m cold, I’m hot, this scratches, my feet hurt, this purse is heavy – please hold it, etc.).  In fact, once you are dressed, look at yourself in the mirror and repeat a few times, “I will not complain on this date.”  Good, now you’re ready to go.  (OK, I’m exaggerating….a little.Second, “comfortable” means wear something you are confident in.  If you are visibly self-conscious, that’s a distraction.  If you are constantly tugging down your skirt, pulling up your strapless top, talking about the fact that other people are staring at you, etc., that’s a distraction that makes you look nervous or self-absorbed.And yes, I’ve had the occasional date that seemed derailed by what the girl wore and how it made her feel (inappropriate to the venue, uncomfortable for the planned activity, inappropriate for the weather, and yes, someone who complained about her feet hurting every five minutes (so why did she wear those shoes?).  I just think that the early dates should be as distraction-free as possible, because you want to focus on each other.  But I could always be wrong.
  3. Don’t show up all spanxed out.  This is false advertising.  I know, girls don’t want to hear that, but it’s true.  We want to see you for you, not the tucked-in, trussed-up, ratcheted-down, corseted, lifted, sculpted, Wonder Bra-ed version of you that does not, in fact, exist in real life.  That doesn’t mean thrown on some shapeless, frumpy, moo-moo as an alternative…it just means that whatever you choose should be an honest reflection of who you are.  If you want to be appreciated for who you are (and who doesn’t?), then don’t be afraid to show up that way.  We understand that no one is perfect, and we don’t expect perfection (lest you expect it of us!).
  4. Don’t wear your “dating uniform.”  To quote Sarah, —  “TRY.  That’s it.  Effort.  [Men] love a [woman] who gives THOUGHT to us.  Effort is at the root of romance.”  We don’t want to feel like we’re just date #572…where you put on your “1st date” go-to outfit, pick up your lunch pail, and go to work.
  5. Calibrate the “revealing” aspect of your outfit to where you want the date to go.  If you’re not sure yet, err on the side of demure.  I did not say err on the side of the masculine (for most women, pantsuits are as difficult to pull off successfully as very short haircuts), just go a little more conservative if you don’t want him to focus exclusively on “those” thoughts (remember, he’s a guy, those thoughts will be there even if you show up in a burqa).  If you don’t want to be complaining to your girlfriend that he never made eye contact above your neckline, then don’t where something that makes him spend the entire dinner hoping for something to slip out.  I’ve had girls show up for dinner at a restaurant in VERY revealing clothing, and I almost think that’s a test – if I glance down, I lose.But if you do think you want the date to go there, then anything that leans towards descriptions like “short”, “tight”, “low cut”, or “see-though” (or my favorite – all of the above) is probably a good thing, as long as it manages to remain at least somewhat classy/tasteful, and does not cause others around you to think “who let that trollop in here?”  If meeting his parents for the first time, avoid anything with two or more of the aforementioned adjectives – remember, one is fine, two or more, and you’re “that tart that Raul brought over for dinner”.  Not good.

Well, them’s the rules.

Aside from doling out advice for the women of online dating, Raul enjoys traveling, cooking, fly fishing, scuba diving, reading and, in general, getting krunk.
He currently works as a steel drum virtuoso in an internationally-recognized Calypso band.”

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