The Art of Date Improvisation

I used to believe that planning dates was an important thing. Figuring out all the logistics in advance seemed like the best idea. However, over the past year or so, my mindset has completely changed. As someone who lives radically in the moment, I rarely make any plans at all more than a week in advance, I don't even start considering date ideas until at least the day before the date, and I never solidly plan any date anymore. Instead, I mentally sketch a general idea of what I might feel like doing and leave plenty of room for improvisation. The result of an improvisational approach to dates? Dates are a lot more fluid, a lot more enjoyable, and any obstacles or deviations completely fail to bother me. I welcome change and unexpected turns of event.

There are several crucial elements to improvisational dates. In many ways, improvisational dates are very similar to good jazz solos, but there are certainly a few differences.

Have an Array of Possibilities Beforehand
Improvisation isn't about coming with stuff completely out of thin air. Instead, it's about having a wide range of possible directions to go, and choosing them in the moment, in accordance with the present mood. As such, before the date begins it's vital to have a mental list of possibilities. This can be a list of various venues that you might feel like visiting, or this might be a list of various activities that can be done at a given location. Your array or choices can be as broad or as selective as desired. A simple improvisational date list might be as simple as Outdoor Activity (go for a walk, play frisbee, kick around a soccer ball, or play at a playground) followed by a Meal (grill steaks at home, grab a burger from In-N-Out, or pickup Chinese food) and then relax at home (listen to new CD, play video games, cuddle and watch a movie, or play cards). That simple improvisational framework offer 48 possible dates, consisting of only three different activities. The vastness of your array of possibilities is limited only by your imagination.

Establish Proper Expectations
This one is fairly obvious, but it's also an absolutely crucial one. Given that improvisational dates aren't always "tried and tested," it is important that both you and your date have no solidly set expectations for what will or will not happen. Disappointment and dates don't mix especially well and they often don't end well, either. As such, it is important for you not to count on certain things happening or working out perfectly, and it's important for your date not to have any misconceptions about what you might end up doing or where you might end up going. The simplest way to eliminate false expectations in your date's mind is simply not to tell her where you're going or what you're doing. Not only does this circumvent any misconceptions or problematic expectations, but it also serves to enhance your aura of mystery.

Be Confident and Decisive
Since improvisional dates often change on whim, it is critical that you remain perfectly confident and firmly decisive. Displaying these two leadership qualities well communicates the subtext that you can be trusted and that no obstacles deter or bother you. When you are confident and decisive enough, your date will never even know whether a given adventure was pre-planned or improvised. In her mind, it all flowed together so smoothly and seamlessly that it hardly seems like the result of improvisation. When things don't go as smoothly as planned, she has the opportunity to see that you can dynamically handle situations as they arise. Either way, you win.

Improvise Based on the Energy of the Date
Since the chief focus of the date isn't the venues visited and the activities done, it's important to keep the interpersonal vibe the central focus of the date. The best choices are made based on the level of energy and the present vibe of the date. If the two of you are starting to reach a lower-level of energy, it probably isn't a good idea to go for a three-mile run or begin an indepth discussion of quantum physics. Likewise, if the mood is starting to get more personal and connected, it probably isn't a good idea to do something that involves competition or puts too much physical or emotional space between you and your date. Instead, the way you improvise should capitalize on the flow of energy and serve to further direct it. Some of the best dates are ones that have contrasting levels of energy or vibes. This serves to engage both people's emotions more fully and creates a more visceral experience.

Most Importantly, Have Fun!
In the end, the whole point of improvisional dates is to have a good time doing some fun things with a person that you like. As such, it is important to only choose elements that will be mutually enjoyable. If one of the ideas you previously thought of doesn't seem like a fun choice, don't do it. If none of the options you have in mind seem fun, then throw them all out and choose something else. If something you're doing is even more fun than you expected, then do it for longer. If something you thought would be fun ends up being quite dull, don't waste any more time on it--change activities right away! There are few things more enjoyable in life than having an amazing time with someone you enjoy being around.