That Star-Spangled Man with a Plan

Look at how the women fawn over him! 

Brace yourselves, dear readers, because I am about to drop some knowledge. Are you ready? Here it goes.

First dates are all about making a good first impression. There is only so much you can get to know about a person over the course of a couple of hours, so in my opinion, the point of a first date is to intrigue the other person enough so that he or she would like to see you again.

Boom. Was your mind sufficiently blown? The goal of a first date is to get a second date? I NEVER WOULD HAVE GUESSED.

Sidebar: The goal of a second date is to get a third, by the way. I’d say this cycle continues until about date five, at which point you’ve certainly established if there’s any chemistry and hopefully have gotten a decent enough sketch of one another’s personalities to determine compatibility, at which point it’s either “Yay! We’re dating!” or “Erm, better not.”

The goal of a first date might be easy to discern, but what’s hard is working out how to achieve it—how do you impress someone enough that he or she might want to see you again?

If you only ever watched romantic comedies for dating advice, you’d probably think that a Big Romantic Gesture is the only way to go. And perhaps for some women (and men), it would be; however, despite what you might think, neither I nor really any other lady with whom I’m acquainted requires a coat thrown over a puddle in the name of chivalry or a boombox hoisted over head, blasting Peter Gabriel.

Sidebar: Even though “In Your Eyes” is totally my jam.

In my favorite John Hughes movie, Some Kind of Wonderful, the main character, Keith, played by a delicious, young Eric Stoltz, plans a crazily elaborate first date with the most popular girl in school, Amanda Jones.

Sidebar: Amanda Jones—definitely no minor-leaguer who would be swept off her feet by the touch of his amateur lips—God, I love this scene. If you haven’t seen this movie before, drop what you’re doing and rent it—what? It’s not on Netflix OR Amazon Instant? That is soooo disappointing.

The date involves (aside from a standard fancy dinner) his best friend, Watts, playing chauffeur all night, and breaking into an amphitheater and later a museum where Keith has temporarily installed a portrait of Amanda that he drew himself, as well as a pair of diamond earring purchased with money from Keith’s college fund. All of these things went over about as well as you'd expect them to.

I remember the first time I watched it (in a class on marriage, of all things), I thought that Keith was adorable, but also a little creepy, what with the stalker drawing and expensive gifts. The execution was way too much, but he did do one thing right: as insane and extravagant as his plan was, he did still have a PLAN. Not only did he have a plan, but it was also one that required no small amount of forethought on his part.  

And for me, that’s the number one way to impress me on a first date—showing forethought. I don’t need flowers, or chocolates, or a $100 dinner. I certainly don’t need jewelry. But it absolutely kills me (in the best possible way), when a guy I’m going out with clearly put some thought into our evening together and didn’t show up at my door with nothing more than the question, “Soo…what do you wanna do tonight?” Ugh.

One of the best dates I’ve been on was with a guy I went out with last summer. It was basically a blind date, set up by my brother-in-law who worked with the gentleman in question. My BiL didn’t tell me much ahead of time about Phillip other than a cursory, “He’s a single, employed Aggie Catholic—what more do you want?”

Sidebar: Not much more, actually. That’s pretty much the dream, amirite?

I assume Phillip got the same kind of abbreviated biography about me, so neither of us went into the date knowing what to expect of the other.

Phillip first impressed me with his willingness to pick me up at my sister’s house where I was staying for the weekend—it was out of his way, and he had to contend with not only my brother-in-law who has a bachelor’s degree in winding people up, but also my wedding-obsessed niece and nephew who would naturally assume that this young man was here to marry me so I might be Maiden Aunt Sissy no more, which is not intimidating or awkward at ALL.

Phillip handled my brother-in-law’s teasing and niece and nephew’s sweetly embarrassing questions with aplomb. What was even better was once we finally made it out to the car, I found out he had researched not one, not two, but three options for drinks. All were slightly different—a tapas bar, a charity saloon (so cool!), and a gastropub—and all were within walking distance of one another, so if one place wasn’t to our liking, we could try someplace else.

It was clear that he even though he didn’t know much about me, he had spent some time thinking about what might be fun to do, and I was so appreciative of his attention to detail. Each choice was unique to the city and offered a slightly different mood, and it was great to be able to have some actual options from which to choose. Phillip showed up prepared, and that was awesome. I had a great time that night, and I hope he did too, and had we lived in the same state (and had I sufficiently impressed him enough to ask me out again), I definitely would have gone on a second date with him. 

This advice isn’t limited to just guys planning dates, or even girls planning dates. We as people in general like to feel special, and someone taking the time out of his or her day to put together a plan—whether it’s a romantic twilight picnic date at Miller Outdoor Theater or a Sunday brunch at your bestie’s favorite restaurant to celebrate a new job or a fly fishing trip with your dad just because or remembering to send a note to someone going through a rough patch—is bound to make whomever it is you’re treating feel important. And that’s something that we can, all of us, learn to be better at doing.