I’m going to be completely honest. This whole thing started because upon venting about how I’m struggling to stay a-float with real work and blog work and freelance work and The Hook-up Conversations R said, “what can I do to help” and I jokingly said, “write tomorrow’s blog post.”

“I thought you’d never ask,” he said.

And so began what I assumed would be the beginning of the end of our relationship.

“Explain to me again why you broke up?” I envisioned friends and relatives saying.

“Well he just could not structure a blog post to be both informative and entertaining! I did what I had to do…”

Luckily R seems to know his way around a 20-Nothing topic, and put together both an interesting topic: how to behave on a first date with an interesting twist: I don’t want to give it away. Best to read for yourselves.

Enjoy! And thanks to you – and him – for patience as I wrap up some non-blog projects and get back to focusing on my thrice weekly routine here.

(R’s post begins here, but that will become clear by the use of proper grammar.)

First, I want to say that I’m genuinely honored you allowed me to post on your blog as I know this is not only an opportunity so few have received but that you easily get nervous and skittish about what I’m going to say next to the general public – especially when it has to do with relationship stuff. Even when we approached the idea of me tackling this topic, I could sense a little more apprehension than pure excitement. I’ll do my best to not embarrass you and hopefully dole out some helpful advice. Here goes nothing.

As J can attest, I tend to keep things short and to the point. Which as I think of it now seems to be the exact opposite of what a blogger does. Not that you ramble J, but often you ask me relationship questions and my one-line responses leave you less than satisfied. Take for example the time you asked me my take on the chameleon dater (for those new to the blog this was the idea that there’s a type of girl who changes her personality based upon the guy she dates). My response: “A girl who changes to what the guy wants? That’s awesome. I encourage that.” This response led to my first experience with J’s “harrumph”. So know that my forthcoming advice will be mostly brief, somewhat tactlessness, but absolutely invaluable.

Here it is: Ladies: “think like a man, but act like a woman.” Guys: “act like a man, but think like a woman.”

What does this mean exactly? Let’s start with the women.

The first half of the statement is “think like a man.” Why is it that girls always say “being a guy is so much easier?” That’s because for the most part it, it is. Guys tend to not over-analyze, not stress, and certainly not care about the small things. We tend to be our true selves off the bat more often – sometimes to a detriment, but a genuine one.

On a date, try to adopt our lassie-fair attitude. Don’t analyze each word that comes out of his mouth, don’t be concerned about ordering that side of mac ‘n’ cheese (because it’s probably going to be excellent). What would a guy do? He’d order that mac ‘n’ cheese because it comes with bacon and bread crumbs and that’s always delicious. Look, someone is going to stutter through a sentence or say something that may slightly offend you. Like when J told she didn’t like Bruce Springsteen, I may as well have left her at the bar then and there. However, despite my continual attempts to prove the glory that is The Boss, I know that any relationship – short, medium, or long – will have moments where you and the person don’t see eye-to-eye. Let them go. Be the self who you really are. If you are a dork, dork it up on that date. If you loved the Watson episodes of Jeopardy (which I still can’t stop thinking about), then talk about it. At the end of the day, guys want to see that fun side you have even if you are slightly embarrassed by it. We don’t want the version of you that you think makes the best impression. Guy’s don’t do that, and we certainly don’t want that. We want the version of you that makes you most comfortable.

However, the advice is not to be a man, but think like a man. At the end of the day, we want you to “act like a woman.” Now I know this can mean a lot of things to a lot of different people but at the end of the day, it’s a few simple things. One – show us your caring side. This doesn’t mean reach over and start caressing our hand on the first date as we tell a story, but be engaged and show interest. We will do our best to make you comfortable (guys get ready for my upcoming advice) so show a little maternal instinct and care about us a little. In a word, be sweet. Two – be flirty. Guys like women that seem into them, so if you think you are into him, show it. That line of not wanting the girl to come on too strong applies to one out of fifty guys, in my opinion. Most of the time, we’ll get excited that you are into us. And three – look nice. We know you like to get dressed up for first dates, so go for it. We’ll appreciate that you took the time and we want to see you excited about the date. Looking good will remind us this is a date and we need to treat you special that night.

For the guys, let’s start with the second half of your advice which is “think like a woman.” This means you anticipate what she’s probably going through before meeting you. She’s probably nervous, concerned about what to wear, excited to be going on a date, stressed some from work thing, etc. Assume it’s basically the entire gambit of the human emotional spectrum bottled up in a less than 24-hour period. No, I have no idea why that happens, but I know it does. So guys, anticipate that. Think about these concerns (don’t do more than that though) and with all this knowledge of what she’s thinking about ….

The most important part of this advice: “Act like a man.” Take some initiative, man up and set the tone early that you are going to make this a comfortable and fun first date. Let’s break it down with some examples.

• You think that she thinks: “I don’t know how long I am going to need to get ready for tonight. Your act: Make a specific time you will pick her up (and yes pick her up) that is a reasonable time post-work and don’t be late. And do tell her your plan a few days before the date and remind her that morning. This way she should feel comfortable preparing to and minimize the amount of stress that goes into that.
• Second example. You think she thinks “I hope we don’t go somewhere lame/too fancy/too expensive/too cheap etc. You act: You pick a place that is your personal favorite and tell her so. She’ll appreciate you bringing her in on something that’s important to you but she’ll also be comfortable knowing that you are comfortable there.
• Third example. You think she thinks “I am not sure I look right for this date”. You act: Very simple – tell her she looks great regardless of what she’s wearing and tell it to her immediately. This is a no-brainer and will go a long way.

Basically guys, think about what any woman could be nervous about going into that date and act accordingly to make her as comfortable as possible.

And last but not least, the classic conundrum of to kiss or not to kiss on a first date. To me, there’s no rule on this (right J?). Go for whatever feels right in that moment. And here’s why – if you tallied up all the relationships in the world that have ever happened over the long course of time, no one would tell you that the whole deal rested on the first-date kiss. Don’t go by a standard rule because there is none. If you two are feeling it at the end of the date, make it happen. If there’s no second date then whatever, you got kissed. And if there is a second date, great. You both know you are into each other, and what could be bad about that.

And that’s it folks. Good luck on your first dates everyone. Hope this helped and J, hope I didn’t embarrass you.

image credit.