Posts Tagged ‘How to dress for a first date’


     On Thursday last week, I had planned to meet a few potential wingwomen.  These promising ladies may be useful later on in my 2010 quest for finding a New Year’s date, but I don’t want to get ahead of myself…

     A few hours before my Lady Date I was perplexed as to what to wear, as some of you may have seen from my tweets.  What does one wear when meeting a woman that you are hoping to see again, should things work out?  Territory in which I’m not familiar.  No real need to show off my cleavage, but if they took to the “wingwoman” title seriously, I need to show them I have the goods to assist reeling something in, whether for myself or the good of the team.  One was latina, who could out curve me, not needing the assist.  However, the other two were Asian, and they most likely will view “my mangoes” useful.  Went with a light V-neck sweater and jeans. 

     Since I chose a place downtown, I figured, why not multitask?  I had a coupon for a store that was about to expire and needed to run to the bookstore.  Hopped on the train and headed downtown with plenty of time to spare.  First stop, Victoria’s Secret for my free pair of underwear.  Under normal dating circumstances this would probably not be a store I would head to.  And not that I thought the night would lead to needing a change of panties, but if it did, I was now prepared.  Forewent the pink striped bag and just shoved the tissue wrapped garment in my purse.

     Next stop, Barnes & Noble.  Scurried over to the self-help section and there was one copy left of the book I was looking for.  This book is key, for my 2010 project.  Headed to the counter, paid, and nixed the bag there too.  Shoved the book into my purse and headed to the lounge.

     As hoping, arrived about ten minutes early.  Now had ample time to reorganized purse so that my wallet was on top of self-help book and bikini briefs.  Would really love to avoid making an ars of myself on the first meet by pulling out an ATM card with a side of underwear.

     Meet time came and meet time passed.  Ten minutes later one showed up (traffic).  About ten minutes after that, another showed up (Who knows the reason, but she did text to say she’d be late).  And the Latina, after saying she’d be there, never showed (standard LA flakage).  Her loss.

     We ordered drinks, food, and got to chatting.  Miss Independent is originally from the Philippines but has been in LA since she was a child.  Mid-thirties, likes to grab a beer on occasion, and has no problem going and chatting it up with a guy at a bar.  Shop Girl is originally from southern California, but is of Taiwanese decent.  She is more traditional old-school Asian.  In her early thirties, thinks window-shopping is a form of exercise, and aspires to be a housewife.  Shop Girl has a sunny disposition and Miss Independent is a little more matter of fact.  

     Both seem to be very strong in their opinions, but not opposed to hearing those of others.  This was made clear when we were swapping date stories and Shop Girl mentioned online dating and Miss Independent said she never did/would because, “if it ain’t broke don’t fix it.”  After hearing some of my date stories, Shop Girl asked if I was collecting them.  Man, she has no idea and I wasn’t about to tell.  I figure I can ease them into the blog, if at all.

     At one point, before I knew what was happening, there is was.  My mangoes made it into the conversation with Miss Independent making a flat-as-a-pancake hand motion and telling me I’m not Asian, so I don’t have to worry about it.  Good call on the V-neck.

     All in all it went well and we are planning to meet up again.  On the flip side, I did ask them, since they are both from LA, about some places to go hiking, since I’ve never been around here and I hear it’s great.  I don’t want to be locked in to just meeting up at bars and lounges with them.  Nonetheless, Shop Girl said yoga is as strenuous as she gets and Miss Independent flinched, made a face and said she doesn’t like getting dirty.  Hmph.  Looks like I may need to repost my wingwoman ad and try to find a woman with a little more tomboy in her.  Because window-shopping – doesn’t work for me.


Next Up

          I think either person can initiate the first date.  If you just keep emailing, you might as well list that you’re only looking for a pen-pal. 

          And those class acts who email their number in the first email – seriously!?  They’re usually the ones who have the 2 line bios and interests in MMA and UFC.  Dude really, what could we possibly have to talk about?

          If you’re emailing back and forth for a while and you enjoy reading and writing them, it’s probably a good idea to do an initial meet.  When I told my best friend I was having my first meet she quickly asked, “What are you wearing?”

          “I don’t know,” I said.  “I haven’t thought that far ahead.”

          “I know, that’s why I’m asking,” she replied.

          Not fitting the mold of most women, what to wear is not usually the first thing on my mind.  Don’t think it even makes the top 5.

          I have a whole theory on how to look for your first meet.  Many little factors come into play, but here are the basics.

          When you decide to meet there’s usually a number exchange.  So, there’s either a phone call or text(s) involved.  If you’ve talked on the phone and the voice matches the emails and you’ve already decided you kind of like the person, put a little effort into your appearance – but not a ton.  If you’ve emailed and called and/or texted and it’s going to come down to physical chemistry to make up your mind, just be your regularly dressed self.  If you’ve emailed and exchanged numbers and then there’s an abundance of texts – which has happened to me more than I’d like to admit, you begin to dread the first meet.  At this point I get the feeling that the guy likes me way more than I like him.  So, to dress for this meet, not much effort – no frills.  I’ll show up clothed and little, if any, make-up.  Here’s why:

          He already likes me too much.  I don’t want to be looking too attractive just to have him like me more when I’ve already partly decided he’s a tool.  This works well for me because I have yet to have any of those guys turn out to be keepers.

          However, some of them are still excited and want to see me and all my frumpiness again.  They’re either desperate or I have some hidden “wow” factor to which I’m completely unaware.