While setting up a first date or a date to a new spot she hasn’t gone to every now and then you’ll get lucky and you’re date will ask the greatest question a girl can ask a guy…. “what should I wear”. If you get asked this question by a potential date, for the love God, don’t mess this up. Now there’s two ways of this happening by chance OR if you’ve been in the game a while you can actually get her to ask you the what should I wear question. The trick is in setting up the date and hinting at possible venue changes. Also as much as you might hate it, this means a weekend date is a must. This is a recent phone conversation I have setting up a first date. Her: So where are we going this Friday VK: I thought we’d start at this nice little Sushi spot/ Italian spot, then relax at this little lounge or Hotel Bar I know then maybe if you can keep up we might check out this new club my promoter friend keeps bugging me to stop by at. Her: ok, that sounds like fun. Lounge to new club…. what should I wear VK: I’m suiting up but that’s just how I roll. Just to play it safe, why don’t you throw on some heals and a little nice dress and show off those legs (this was in August). Her: Oh really, anything else Mr. Boss VK: actually now that you bring it up. Yes, I like cleavage but that’s just me.

I’ve had a variation of this conversation over the last couple of months and depending on how funny and daring you can be with the girl, I’ve also used the term, “slutty tight dress” or “something that shows of those curves”. The point being is when you tell a woman what you want to see on her it’s silently sets the bar high for her beauty and attire to visually please you on this date. I’d say 95% of all girls want to get dressed up and sometimes need to be told to do so. In DC a lot of women play it safe and go with nice jeans, a dress top, “sensible” shoes. In this city there is a fear of sticking out too much and being judge by other girls who are “too cool” to put up their best on a date. I also think the real grown up “Date Night” is becoming a lost art among young men lost in the world of putting in little effort to get the best result bang. But like most things with me, the best time to do something is when no one else is doing it anymore.

When you tell a girl to dress up for a first date not only is the bar on visual set high, the bar for the whole date is set high. She has to actually shave her legs, step up her make up and hair game, wear a dress and thong or go commando (meaning hopefully wax or landing strip). The night just turned from casual no big deal dinner and drinks to this might be a date with my future baby daddy shit. The time and effort to prepare for the date plus gravity of the date means you can either blow it big time or knock it out of the park. After that you show up, compliment, tell a joke, give longing glances, order shots, two songs on the dance floor. Call it night, thank you cum again. Wait you do know how to entertain a woman for a whole night, correct?

I’ve found American girls are ridiculously lazy when it comes to this. Girl: Sooo what should I wear? Me: Well, it’s going to be a classy night so make sure to dress sexy. Girl: Mmm *shows up in brown sandals* Meanwhile, my Turkish girl (wearing stylish cutoff T, skirt, heels) Me: I thought you were going fancy tonight… Her: I am so sorry! Here I will go to change right now