Tuesdays with the Pretty Girls: The First Date

Gents have questions about ladies. What better way to get into the minds of a gal than to directly to the source. Luckily, a few lovely lasses have signed on to answer the questions plaguing the guys. First, meet the panel.

Sara N. Carpeaux / Dallas, TX

I’m a girl who enjoys being a girl. My closet is equal parts classic, tailored simplicity and relaxed femininity. I wear clothes that entertain me. Like any good private school east-coaster, I posses a soft spot for blazers, plaid and the color navy. I adore shoes and own an (almost) excessive amount. My thoughts: know who you are and what looks best on you, find a good tailor, pay attention to details; have fun with the rest.”


Jenny Yamaguchi / Sunny California

“Classic girly girl, inspired by the boys. ‘Cuteness is my weakness.'”


Rebecca / Los Angeles, CA

“I like vanilla ice cream, but not things that are “vanilla”.  Keep it spicy, but not in my food.  Good manners, humor and rhythm go a long way.”


Yekaterina Burmatnova / New York

Student, model, entrepreneur, band manager, stylist, writer, fashion expert, a one woman show. When it comes to style i am all about mixing and matching, a dress from a thrift store and an expensive pair of shoes.
I live by “Liberators don’t exist, people liberate themselves.”


Jennifer Aull / St. Louis, MO

“Do your best. I’ve been quoted before, life doesn’t come with an instruction manual. At the end of the day if you’ve done you’re best, that’s all we can ask for.”


Let’s get it going. This week’s question:
Lawrence wants to know: Becoming a ‘real person’ (aka an adult) is an interesting transition especially when it comes to dealings with the fairer sex.  This isn’t college anymore and you can’t just meet girls and chat them up in a fraternity basement, though it would be awesome if I could still do that without having part of my soul die.  Maybe it’s the crowd of degenerates I roll with, but first dates seem kind of rare.  Should we ask you out to coffee? What’s the preferred move?

When you see a pretty girl, just smile and say hey. That’s step one.
Then you should ask her if she is free to meet you for a drink sometime this week. Give her options, just because she can’t grace you with her presence tonight, doesn’t meet she isn’t interested. The drink date will be long enough to find out if she is someone you’d like to see again.
Then feel free to ask her out or make a quick exit.

When planning a first date, one of the most important things to consider is how well you know the woman.  If you’ve just met and only know her first name/location/job and preferred drink, then I’d say stick to a safer date, i.e. coffee shop.  However, if it’s a woman who you’ve known for awhile or even a friend, then it’s fine to be more adventurous and creative.  Great first dates with someone you just met:  coffee shop, karaoke bar, the zoo, comedy show, cooking class.  Great first dates with someone who you know better:  sporting event, theme park, flea market, a hike or a picnic.    The most important thing is to make sure your date feels comfortable so you can make it to the second date and beyond.  We all know awkwardness and uncomfortable silences blow.

There are basics that may not need to be covered for first date advice, but for the sake of thoroughness, I should probably mention a few.

Resist just inviting her to your place (creepy…actually, really creepy) or the loud sports bar relegated for boy’s night. It’s a mood killer telling you about our day, or really anything, in between touchdowns. It’s rudimentary knowledge––but my girlfriends and I can attest it happens.

The ultimate goal is setting the stage to discern a bit of chemistry that might warrant date number two. You want to get to know her, so the location should be quiet enough to carry on a good conversation without being so sterile it magnifies the inevitable awkward silences (and you find yourselves staring blankly at each other, the floor, the salt shaker, desperately grasping for a topic). Atmosphere is a must; people watching, a picturesque view of the city, music that sparks a common love for a band, or something as simple as darts at a local haunt immediately give you something in common and might bring out a more relaxed or playful side of her.

Something to keep in mind is where or how you initially met. Preferably, you already know an interest or two of hers, so find something in that vein…it shows you’re paying attention. If you met her randomly and have little context for her interests, keep it simple; simple, but creative. Creativity goes a long way, gents, it shows effort and thoughtfulness, even if it’s not a complete success. Pick somewhere familiar where you can be yourself; yourself on your best-looking, most witty day. I think coffee or drinks is effective if the place has some character…an interesting story, some place more stimulating than a Starbucks. After all, if it’s meant to be, do you really want to celebrate your one year anniversary with a caramel skinny latte?

First dates are rare and totally lack sweetness.
First step: Definitely approach the girl and make the first move. Don’t be shy and being nervous is ok. Sometimes we get a little shy, as well.
Second: Ask us out for coffee or dinner, but really, be creative. Take us to a picnic or the museum, it’s fun and different. It’s making the first date feel special. Besides, We can always go out to dinner.
Third: win us over with your charm and humor. What girl can say no to a witty and clever guy?

If you can follow these steps, then you will have won our hearts over!

This is a delicate question as I have been on a few general ‘good dates’. What can I say, I’m rather lucky. I will only mention the bad dates now, that end— or he tries to end them with sloppy make out session, drunken stupor, or club going night out, in which I can do by myself.

Call me a traditionalist, but the last real date I went on was with a friend who took me to his high school re-union. He picked me up at a friends where I had gotten ready, brought me flowers, and even opened the car door for me.  Sure, it wasn’t just the small gestures that seemed to put me on cloud nine, but there were two specific behaviors that left me wanting more. He led me into a room that was full of familiar faces to him and as son as he saw I wanted to scream and run, he led me in by the small of my back and made me feel comfortable.  Yes, the alcoholic beverages he offered may have helped but the conversation was that which no one could fabricate. We talked amongst his friends of books, politics, local fare, and general ‘good’ gossip— there was no bashing. At the end of the night, he gave me a peck and that was that. I was left in the hands of my girlfriends and friends to ask the question, ‘what the hell just happened, and did I do something wrong?’ In fact I didn’t.  It was just a perfect night. He moved over seas and visits now and again. Age difference too may play a small factor but seriously, it was one of the better dates in my years.  After all, we can all find those guys who take you out to dinner, a movie, and try their swoon tactics to just get in your pants at the end of the night.

My answer is to ask me out genuinely; and no, going to a club afterwords does not constitute a date. Movies dates are fun but only after you’ve had the deep conversation to find out about the other person.  Anything less is just a crush and is better left to the imagination.


8 responses to “Tuesdays with the Pretty Girls: The First Date

  1. All great advice from my fellow females!
    I’d say, stick to the basics. Of course you’re going to be nervous, but I personally think that’s endearing! It’s like saying, “hey, I like you a lot and I don’t want to mess this up.” I think it’s even OK to tell her that you’re slightly nervous.
    I also believe in planning a date together! Ask her what her preferences are and throw out some suggestions. Then, plan something that you both feel comfortable with. DEFINITELY make sure you don’t take her some place where she might be allergic or just not down to try!

  2. Wow…great advice. I think I need to print this out and tape it to the inside of my billfold. 🙂


  3. Will the redhead from Dallas please accompany me to Starbucks?

  4. Yayyy for Rebecca!! Sorry, I’m biased. Anyway, I like a cozy picnic at the beach that turns into a flirty food fight, leading to rinsing off in the ocean, and ending with a walk into the sunset- my ideal right there. Bonus is if you find me a pretty seashell on said walk so that I can keep it on my nightstand and if it all works out, I’ll then be able to remember that first date 50 years from now when I look at that shell.

  5. No, she will not. Show a little effort Castleberry!

  6. loving this post x

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