74: First Date Cheat Sheet
Monday December 14, 2015

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~The Simple Sophisticate, episode #74

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The internet is full of dos and don’ts when it comes to first dates. After all, there are so many unknowns because potentially both parties are complete unknowns to each other ratcheting the uncertainty level even higher. And while each first date experience will be different, the one variable you have control of is you.

As I look back on the many different first dates I have had, the one thing I’ve learned is to stop worrying about impressing and start seeing it more as a fact-finding mission. Now, don’t misunderstand, I am not suggesting that the first date be interrogation 101, but the goal is to see if there is any compatibility.  Sure you both said yes to the first date, which means there was mutual curiosity, but is there potential for enduring connection? That is the guiding premise.

1. Schedule when you’re available

Any set “rules” should be tossed. Schedule your date for tomorrow, schedule for next week, schedule it for tonight. It doesn’t matter. The key is that you are scheduling it when you are available based on all of your other responsibilities, hobbies and interests. Immediately, your date gets to know what you enjoy doing, what your career demands, etc.

2. Don’t let the physical attraction be the only selling point

Recently, Psychology Today reported that basing our potential partners on how physically attractive they are did not ensure  a relationship that would deepen or endure. In fact, once the “cute” factor wore off, the glaring differences and incompatibilities were reason enough to lose interest entirely.

Admittedly, there must be some level of attraction, but the key is to ask yourself, why am I interested in this person? What non-physical qualities do I respect or find attractive? Are they thoughtful, generous, intelligent, humorous, disciplined, determined or any other number of reasons to be interested in them? After all, someone with whom you wish to be in a relationship in must be more than just eye candy.

3. Express appreciation

Finding the right balance between nonchalance and adulation is imperative, but when in doubt, say thank you for opening the door, paying for the meal, opening your car door or any action in which your comfort or enjoyment was taken into consideration.

4. If you want a second date, be honest

Most likely, you will have a vibe to gauge their interest. Perhaps it is based on comments made during your conversation, body language or how the date when (did it end abruptly or go longer than expected?). But before the date concludes, just make it known, “I’d like to do this again”. State it short and sweet, don’t go on and on. At this point, the tennis match of reciprocation has begun and you can gauge how they respond.

It has been my experience as I have been dating in my thirties versus my twenties, that fewer games are played and directness occurs much more often (that is of course if the other person is at least in their thirties). Also, there is no need to wait three days (or whatever the set # of days the “rules” require) to text or call and set up the next date if both parties are interested. Texting the next day to briefly say you had a nice time shows interest and intention no matter when the next date may be.

5. Engage in equal inquiry

While both sexes receive the advice of letting the other party talk while you listen, it is crucial that the sharing be evenly distributed. After all, you’re looking for a partner that wants to be with you because of who you are, what you bring to the table.

6. A trailer, not the entire movie

The gift of a first date is that the slate is clean, no mistakes, no oopses, no gaffs or faux pas. But it also doesn’t mean the person is your trusted confidante. Introduce yourself, don’t expose yourself. Mystery is attractive initially, maintained mystery, keeping up the walls after much time and investment has passed is another story, but initially, aims to offer a glimpse of who you are and what excites you about life.

7. Authenticity invites authenticity

The best way to get to know someone as they truly are is to be yourself. Being vulnerable creates a safe place for the other person to open up as well. Now, not everyone will engage, but on the first date if you want all the compatibility meters to be read clearly and accurately, you must show (what it is you do show) the truth of who you are.

8. Let go of assumptions

Since a first date is typically a few short hours (if that), the conversation may cover a lot of ground without going too deep, or you may just touch on one or two topics and discuss and get to know the person one a single dimension. Due to this, while we should all pay attention to red flags, don’t jump to conclusions that were shown because of assumptions based on other similar scenarios. Give the person a chance to reveal themselves.

After all, there are many stereotypes and ignorant assumptions that are made because the person doesn’t have the experience of knowing someone like you. Your background, your experiences assisted tremendously is helping you to arrive where you are in your life. The person you are on a date with can’t possibly know all of those twists and turns in one date. Therefore, have patience in getting to know them as you would hope they would do with you.

As Steve Martin’s character in It’s Complicated states over his Croque Monsieur with Meryl Streep, “dating is exhausting”.  As we are trying to be cognizant of our presentation, trying to be our best selves, trying to be our authentic selves, emotionally putting ourselves out there, each of these elements alone is taxing and demanding, let alone, all of them at once.

Most importantly, be kind to yourself. Whether the first date leads to a second date and beyond, or even if it leads to a second date that reiterates your concerns from the first and everything ends there after, at least you gave it a shot and broadened your perspective of who lives in this big, amazing world.

Dating allows us to assess ourselves, where we are in our lives, and what kind of a partner we are capable of being, but we mustn’t become too self-critical. Few people will mesh with us if we are being ourselves because the person who does eventually reveal themselves to be compatible will understand our interests, laugh when we laugh, appreciate our trajectory and how we have landed where are are in our lives today. And that won’t be everyone we meet, even if initially we think they might. That is why we go on the first date.


~5 Components of Strong, Healthy Relationships

~10 Simple Ways to Be More Charismatic

~Grown-Ups vs. Adults: 15 Differences

~Petit Plaisir

~Love the Coopers

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