Ask Drew: Anatomy of the Perfect First Date Outfit

Yeah, you read that title right. I’m telling you what to wear if you really want to capture a guy’s attention. I know you think you know what to wear, but you don’t. Those women’s magazines that give you advice on “Ways To Dress That’ll Impress Him!” lied to you. Consider the source: next time you read an article about how to dress sexy, or his favorite sex moves, check the author of that article. Unless it’s written by a man, you’re wasting your time. “Cute” as a descriptor for clothing isn’t in our vocabulary. Hell, if we had it our way, you’d show up on a date wearing two Band-Aids and a cork. But unfortunately, this isn’t a set on Boogie Nights, so let me – a man – give you some advice on what to wear that’ll make us act like blithering idiots all night as we mentally undress you. I’ll start (literally) from the ground up.

What Shoes to Wear on a First Date

By and large, we don’t care about shoes, so if you don’t want to take this advice, by all means. However, if you’re so inclined, wear a pair of heels. I don’t know why, but they’re sexy. Not only that, but it’s amusing all night watching you walk around like a pigeon. “But heels make our feet hurt! I wanna wear my flats!” First of all, please don’t. Flats look like expensive water shoes. Second of all, you’re drinking and eating for free tonight. Invest the money you’re saving into some Dr. Scholl’s. EXTRA CREDIT: You really wanna get his attention? If you’re wearing some open-toed heels, throw on a few toe rings. They’re like a removable tramp stamp. I’ve never met a girl with toe rings who wouldn’t at least make it to first base.

Below the Waist
I was having a hard time thinking of examples of things not to wear, so let’s just play it safe. When deciding what to wear, ask yourself how it would make your dad feel. If it would get you cut you out of the family holiday card this year, you’ve done well. Show a little bit of leg and you’re fine. And if you really want to knock it out of the park, there’s nothing wrong with showing some whale tail when you lean forward.

What Underwear to Wear For Date Night

Maybe you’re looking to make tonight a memorable one and you went out and spent $900 on eleven square inches of see-through fabric to drape your lady parts in. If you did, I hope you saved the receipt because we won’t notice. The same way a kid treats wrapping paper on Christmas morning, we’re tossing it all around the room trying to get to the present inside. As long as you’re not wearing adult diapers, it’s all just some over-priced fabric made in a sweatshop. There are better places to spend your money. Perhaps an eighty-third pair of shoes would look nice.

Cleavage. That’s all. You can wear a shirt with a picture of a litter of kittens being tossed into a wood chipper, but as long as there’s some cleavage we’ll be able to look past it. I know you think I’m simplifying for the sake of being a smartass, but I’m really not. We’re not complex creatures. Besides, it’s fun for you too. That means you get to play that game all night where if you catch us looking you get to act all indignantly offended and scold us. “Eyes up here, mister!”

Wear Perfume on a First Date

Wear some perfume. Your olfactory sense is your strongest of them all. There’s one perfume (I don’t know what it’s called) that immediately brings me back to my freshman year of college, where my girlfriend and I are fumbling with a condom wrapper in my lofted bed while my roommate conveniently pretends to be asleep nearby. If you make an impression and stake your claim with that fragrance, every time he smells it in the future he’ll think of you. Romantic, right? With any luck you’ll need a restraining order against him in a few years.

A little bit of jewelry is fine, but let’s not go overboard. I was out with a girl one time who might as well have been wearing a slinky on her wrist. After a certain number of bracelets, you just start to sound like a homeless man shaking a cup full of change.


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Drew is a single guy living in Los Angeles. When he's not bar-hopping with a friend's golden retriever to convince women he has a soft side, he's taking them on short-lived dates. His fickle dating habits and "perspective" almost guarantee he'll die alone. All opinions are his own. Got a question for Drew? Ask away...

Tagged in: advice, dating, what to wear, relationships, love, ask drew, opinion,

Lifestyle / Relationships



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