The first date in any relationship is generally the most awkward. If a relationship can survive past the first or second date, it has far better chances of surviving a longer term. That being said, it is important for both the man and the woman to have the right perspective of how the first date can and should operate in the course of their relationship. Even though there are countless possibilities for what a first date might look like between strangers, two that are mildly acquainted, and even a couple that has known each other for a long time, there are some basic principles and practices that should characterize every first date. 

Before the Date:

If we still use the example from chapter 2.4 where Bob asks Sue for a date on Wednesday and plans to take her out on Friday, then Bob should plan to talk with her (phone call or face-to-face; no texting!) either the day before or the day of the date. The conversation should be very brief. The purpose of the conversation is simply twofold: 1). For Bob to communicate his continued excitement about having even the opportunity to take Sue out on a date and, 2), to make sure the two are on the same page with the particulars of the evening.

In the time between the ask and the actual date, the man and the woman should be doing completely different things. The man needs to be preparing the details and atmosphere of the date and the woman needs to be preparing her heart for the date.

Men: It is the man’s responsibility to create and maintain the entire experience of the date. The man must carefully plan everything from a restaurant to the general ‘mood’ or ‘feel’ of the date. The basic principles for men are these:

    • Select the ‘tone’ or ‘mood’ of your date first. Your pre-existing relationship with the woman will give you the guidance you need. The less you know the woman the less romantic the first date has the freedom to be. If you both are practically strangers, the tone needs to be: ‘let’s simply get to know each other a little better’. If you are closer friends with the woman, you have the freedom to have a more intimate mood, but that doesn’t mean you should have a more intimate mood. Generally speaking, the first date should be pretty conservative. Depending upon how the woman responds will give you direction for dates to come. [Note: If you are complete strangers, consider having a lunch date before having a dinner date.]
    • Based on the tone you want to establish, select the particulars. The particulars of your date involve both the length, itinerary, and complexity or simplicity of your date. First, every first date should be in the neighborhood of 3 hours long. Taking any more time just gives you more opportunity to mess things up. It also allows an obvious dud of a date to end quickly instead of being painfully long. Even if the date is a great success for both of you, it should still be kept to around 3 hours because ending on a high note will create eagerness in both people for a second date. So, bottom line,  a first date is generally going to be dinner and that’s all. Second, if all the date is going to be is dinner, then you’d better get the restaurant right. It needs to be nice, but not too expensive. The more expensive the restaurant, generally, the more intimate the mood (and vice versa). I often use Olive Garden as an example of a restaurant that communicates, “You’re worth a nice meal, but, don’t worry, I’m not ready to propose. . . yet.”
    • Make sure to think through a backup plan. Women are honored and impressed with a man who thinks through a nice evening for them. They are blown away when you show up to the restaurant you’ve selected, realize the wait is an hour long, and you pull plan B out of your pocket without looking flustered, thrown off balance or asking her what she wants to do instead.
    • Clean your car. If you have to spend more than an hour cleaning out the inside of your car, the woman is out of your league. Part of being a man (and not a boy) is learning how to live like a civilized human being instead of a slob. Nevertheless, make sure your car is immaculate. It needs to be washed inside and out. It needs to smell better than good. It needs to have a working air conditioner or heater. It should not make any loud or obnoxious sounds. If your car fails in any one of these categories, borrow someone else’s car. You want to make sure the woman is never embarrassed by getting into our out of your car in public.
    • Clean yourself. The night of the date you must: shower, shave, brush your teeth and wear clothes that have seen the inside of a washing machine since they were last on your body. These are non-negotiable. For bonus points, get your hair cut, purchase a new shirt, or anything else that would communicate to her, “I’m so honored to even have the chance to just have dinner with you.”

Women: Since the primary role of the man in the dating relationship is to initiate with you, it is your responsibly to respond to his initiation. He will be constantly looking for your response (sometimes even interpreting things you do as responses that you didn’t intend to be responses), so there are a number of things that will help you have a successful first date (even if you don’t like the guy):

    • Be confident in yourself. No matter what your insecurities, remember one thing: he already asked you out; he already likes you! In fact, he liked you before you dolled yourself up or put your best foot forward. Relax and be yourself.
    • Figure out where your heart is and don’t jump to conclusions. There will be no resisting the feelings in your heart that come from him asking you out on a date, so don’t bother. However, there is no sense in etching those initial feelings in stone – whether they are favorable towards the guy or not. Based on where you find your heart, you should do what is necessary to make sure it is open to the opposite possibility. If there is a conclusion to jump to in any relationship, chances are that you will jump there before the man will. If you have already agreed to go on the date with the man, give him a chance to make his case; give him a chance to win your heart the way it deserves to be won. Don’t take your heart off the table unfairly or give it to him too easily.
    • Decide on what to wear. I know, I know, this goes without saying. But do you consider what your clothes communicate without saying? For example, let’s say the guy asks you to wear something comfortable and casual like a t-shirt and shorts. Instead of listening to him, you come to the door in a spring dress in full make up and flats. Not only did you communicate disrespect to the man by not honoring his request, now you’re going to put him in the awkward position of either asking you to change or him changing the date altogether (because he was planning on taking you horseback riding or something). If he doesn’t tell you what to wear, your clothing will still communicate to him. It is best to keep your clothing modest and fashionable in order to communicate this message to him, “You’re worth me getting this nice” rather than, “Look how pretty I am – don’t you think I’m pretty?”
    • That’s it, women. You have far less to think about before the date than the men do, so enjoy. But don’t worry, your turn is coming soon.

This is enough for one post. Remember, as always, the method both the man and the woman choose to employ in dating (even before the date) will communicate their message to the other person. The man is and should always be communicating, “You are worth it!” The woman, if she’s interested, should always be communicating, “Thank you. I think you might be too.

In chapter 2.7 we’ll look at the remaining parts of the date: picking her up, while in the car, while at dinner, and ending the date.


Ladies, what do you hope men will do for you on a first date? What do you hope they won’t do?

Men, what are you hoping women will be like on their first date?