Tip #31: Date strategically

Anyone who has read dating advice articles has probably seen the pearl of wisdom that you should observe your date in a variety of settings to ascertain different facets of their personality. While that is true, that is a rather broad generalization of what goes on during the preparation phase. Your role is not to be a sociologist that observes the behaviors of the subject under conditions of dark and light, in hot weather and cold, in a restaurant or a stadium, or on weekends and weeknights. "Dating in a variety of settings" is more than simply varying the venue, time, or activity. What it really means is to strategically find variances that will give you information of how this person will fit into your regular life.

A person will mostly act the same in any kind of a restaurant, in any kind of a theater, or in any kind of a large arena. But those kinds of dates will provide precious little information for what it will be like to spend multiple days a week with that person, unless eating out, watching entertainment, or cheering on a sports team is an enormous part of your life (to which I'd say, try to find more of a life). Those situations are almost always contrived for the purpose of getting to know only a little bit more about a stranger in an easily severable environment. That's okay for the anticipation phase, but once you are in the preparation phase, those arms-length meetings have no place any more. During the preparation phase, dates should be about finding deeper compatibility with the things that each of you value most — things that mean enough for you to devote considerable time to. For instance, if you have a passion for helping the needy, bring your date to a soup kitchen. If you like educating children, have them join you at library reading hour. If you make it a point to friend the elderly, invite them along when you visit seniors (and be prepared to light-heartedly laugh off any kind of insinuation). If you are about helping the environment, ask them go along with you on a litter pickup patrol. You get the idea.

Asking your date to share in the things that are near and dear to your heart is a two-way benefit. On one hand, it will give your date insight into the kind of person you really are, below the facade, and will create more trust about your genuineness. On the other, it will give you insight into the person your date really is, and will provide buckets of data on how well the person would fit into the parts of your life that mean the most to you, which is of utmost importance when determining if there is truly "something" there. This is the time to move beyond just "chemistry" and look for a deeper connection on an emotional level. Set the context for what normal life would include if things go further. It may get a little bit uncomfortable as the person starts to encroach upon your private life, but those are the things that should be acknowledged before you make too big of an investment emotionally.