What Not To Wear - First Date Edition

You know, four years ago when I had my gall bladder removed, I was pretty much incapacitated for eight weeks.  I needed to do something in my off time to pass the time while I healed.

One way I did that was by reading lots of stuff, either in book form, or in online articles. 

A couple of these articles were on first dates, and specifically what men should never wear on a first date.  Being someone who has trouble securing second dates with people, let alone first dates, I read with interest, wondering if maybe I was subconsciously doing something wrong.

Turns out some of their suggestions I tend to agree with.  Some I'm indifferent on.  Some I outright disagree with.  But, I figure that I'd let YOU be the judge.  Of course, I'm going to pipe in with my own two cents on each of these articles of clothing and whether I agree with the idea of them being worn on a FIRST date...but I'm interested in reading some of your comments, because really, how they came up with this list is something I find entertaining. 

Ready?  Let's go!

1.  Pleated KHAKIS - Apparently the person who wrote the first article said that khakis are okay, if you were going to a junior high school dance, but not for a first date.  I kind of have mixed feelings about this.  If I were to go on a first date, I'd probably end up wearing dark wash jeans without holes or tears in them.  But, that being said, if my khakis were neatly pressed (and did not have pleats in them), I don't see any reason why my date wouldn't like them...of course, I am just a typical man here...what do I know?  I say that they're fine...but again, I prefer flat front.  Pleated makes you look bigger than you really are, and that I know from experience.

2.  JOKE TEES - You know the shirts I'm talking about.  The ones that have cartoon characters on them, or the ones that have swear words on them.  Yeah, I agree that those shirts are probably not a good idea to wear on a first date.  Could you just imagine taking a girl out on a date to a nice restaurant and wearing a T-shirt that says "I'm With Stupid"?  Yeah, there's a deal-breaker there.  Mind you, I happen to own a couple of T-shirts that have cartoon characters on them, but I only ever wear them as sleepwear or loungewear.  Certainly not for a night on the town!  I completely agree.

3.  TOO SHORT PANTS - I just want to say right now that while I agree with this one too (I mean, what guy wants to look like Steve Urkel on a date?), I also want to say that as someone who stands at over six feet tall, finding pants is always a challenge for me.  More often than not, I have to wear pants with a 34-inch inseam, and most stores only seem to carry 32-inch.  Different brands offer different interpretations of what a 32-inch inseam really is, and in some cases, I make it work...but it takes a lot of experiementation.  If ever you see me with too-short pants, it's likely an experiment that didn't quite work.  But, yes, I will reserve my 34-inch inseams for the first date.

4.  TURTLENECKS - I guess they'd work if your first date was at a ski resort, but my personal preference is that I really don't like them strangling my neck.  Definitely not a fan.

5.  TIGHTY-WHITIES - Now, here's one that I question.  I get that to many women, tighty-whities are anything but sexy, but to some guys, they bring comfort and support.  And, I mean, it's underwear.  Whatever you wear underneath your jeans is really up to the wearer's preference.  But, again, these are suggestions for what not to wear on a FIRST DATE.  The chances of having sex on a first date...well, I would think that they'd be pretty darn slim.  And, if that's the case, one could wear tighty-whities, boxer shorts, even go commando, and nobody would care because unless you're totally drunk out of your mind, the chances of a first date ending in a motel room are SLIM at best!  Again, some women may not find it sexy, but it's the FIRST DATE...who's gonna know?

As for what comes between me and my...um...Levis?  That'll have to wait until at least date #2.  ;)

6.  BOW-TIE - If you're best man at a wedding, they can work.  If you're Drew Carey, it can work.  If you're Archie Andrews in the 1950's, it can work.  Personally, I don't like bowties.  Will never wear 'em.

7.  NOVELTY TIES - I'm also the type of guy who hates wearing ties in general...but if I have to wear one, I must agree with this one.  Wearing a Sylvester & Tweety tie to a first date is almost as bad as wearing an "I'm With Stupid" shirt.  Just my opinion though.

8.  TUXEDO - Don't most guys RENT these things?  And, even if you do own one, where would you wear a tuxedo?  Though, I must admit, it'd be pretty hysterical if a guy wore a tuxedo to impress his date and the first date was mini golf.  Mini golf in a tuxedo...yep, there's a YouTube video right there.

9.  TOUPEE - This is news?

10.  MAKE-UP - I guess I'd have to know what their definition of make-up is.  If it were up to me, I'd say things like blemish cream and face moisturizer are acceptable enough, and quite possibly Chapstick, if your lips were dry.  That being said, I don't think women tend to go for guys who wear more make-up than THEY do.  Unless, of course, you're Gene Simmons from KISS...

11.  SELF-TANNER - I'd only recommend this look if you were a cast member of Jersey Shore.  Personally, I'm fine with being pasty white, and I would hope that my date would feel the same way.

12.  SLEEVELESS SHIRTS - I only put this in because I don't know where there would be any sort of instance in which wearing a sleeveless shirt on a first date would be appropriate.  I suppose it may work if you had your first date on a beach...or possibly a gym.  Somehow, I don't think it would be very romantic of a first date to jog on a treadmill while listening to a Sweatin' To The Oldies soundtrack.

13.  VEST - This is one I will fight you on.  I mean it.  My personal style when I'm outside of a work environment is something I like to call economic prep.  In short, I kind of dress like one of those Yuppie type people who can't afford Starbucks.  Would that make me a Guppie?  Who knows?  The point is, I have this really awesome looking argyle vest that looks really great with jeans and a plain T-shirt.  It's also an outfit that I have been complimented on by several people.  Therefore, I completely disagree with the idea of a vest being inappropriate for a first date look, because I've found a way that I can make it work, and still look good. 

14.  SKINNY JEANS - It really all depends on what your definition of skinny jean is.  If your definition of skinny jean is strangling your midsection and losing the feeling in your legs...they're TOO TIGHT.

15.  DIRTY CLOTHES - Unless you got abducted by a garbage truck, or slipped in a mud puddle on your way to pick up your date...this should be common sense!

16.  WIFEBEATERS - Again, a classic tank top style shirt (which is also known as the stupid term wifebeater - seriously, I hate that term) is fine...provided you wear them as underwear like they were meant to be.  I'm pretty sure that if I arrived for a first date just wearing one of these shirts, my date would run the other way!

(For what it is worth, I prefer a V-neck myself.)

17.  COLOGNE - I'm not entirely against cologne or perfume.  A couple of spritzes or dabs are perfectly fine.  Dumping the whole bottle over top of you...yeah, that's never good.

18.  EXCESSIVE BLING - I'm very basic when it comes to jewelry.  I just wear a watch, and that's it.  So, when I see guys that have watches, gold chains, piercings, rings, earrings...I'm tempted to hold up a magnet just to see if they'll stick to it.  That would be entertaining.

19.  PAJAMA PANTS - They're okay if you're sick, recovering from surgery, or if you're sleeping.  Not for a date.

So, there you have it.  Now it's your turn...do you agree?  Disagree?  Have any other suggestions?

Of course, this is all for fun here.  The real lesson is that in my opinion, while I feel it best that you do make a great first impression on a first date, once you meet the one that you love and fall in love with, then it shouldn't matter what you wear or how you look.  As long as she loves you, she'll accept your joke tees, your novelty ties, and your tighty-whities. 

Or at the very least, you can compromise.  :)