Chapter 3.1 outlined some principles that could govern a dating relationship over its first several dates. At that point all the definition the relationship needs is simply the date itself. Over those first six to eight weeks the man and the woman are simply dating one another. However, shortly around that time, both the man and the woman reach a crossroads: how much longer are we going to do this? What kind of relationship is this becoming? Are we just having fun or is this for real? Whenever the dating couple reaches this point, it is time to define the relationship (DTR).

First of all, it’s important to realize that this will be the second time the relationship has been defined. It was first defined when the man approached the front-door of the house and instead of pretending he wanted to initiate a friendship with the woman he declared his intentions: “I’d like to take you on a date.” Once the woman said, “yes”, the relationship was defined. Whatever relationship the man and the woman had before that moment ceased to be and their new relationship to one another became, at least for the time being, a romantic one.

Any healthy relationship needs definition on a regular basis – whether two people are friends, dating, or even married. Feelings change, accidents happen, and misunderstandings abound over the course of every relationship and without regular and honest conversation about the relationship itself, it can quietly and quickly begin to die without the couple noticing – until the relationship is practically over. For a dating couple, I recommend having a DTR at least every 2-3 months (married couples a little longer – every 6-12 months).

So, as it was for the man in asking the woman for the first date, so it should be in defining the relationship: he steps forward to initiate the conversation (front-door style) and she has the opportunity to respond either in favor of his request or not. Here’s a basic outline of how the first DTR could go (assuming they are both still interested in each other):

  • The DTR should happen by around the 7th date or the end of the 3rd month – whichever comes first. By that time, both the man and the woman have had plenty of time to figure out whether or not this is something that needs to continue.
  • The man should ask the woman for a date just as he has done six times before. This particular date should be planned so that a conversation can be had at some point during the date. So, the man should be thoughtful in considering the location for dinner and/or where they might go afterwards. He should also consider that the conversation might not go the way he hopes and/or could become emotional for both of them.
  • I generally recommend a nice dinner out and then the couple can go someplace a little more private (but not secluded) to have the conversation.
  • The man should not start the conversation until he is ready for the date to be over because once the conversation ends (no matter what she says), the date also needs to end (no hanging out on the front porch until 3am).

To begin the conversation, the man needs to clearly state his intentions and then remember to give the woman an opportunity to respond. So, he might start out by saying something like this:

“Sue, I really enjoy spending time with you. These past several weeks have been even better than I had hoped they would be. You are [he says 1-2 genuine compliments about the woman’s quality that he has found especially attractive]. Since we’ve been on several dates now, I wanted to let you know that I’m still very interested in dating you and would very much like to continue this relationship. Would you like to continue with me?”

Here the woman must respond clearly and without hesitation to the man’s initiation. If she is not interested in a more long-term relationship with the man, then she must politely decline his invitation. If she needs more time to think about it she can certainly ask the man for that, but she needs to know that the man will likely receive such a response as a passive “no” (This is really the worst option for the woman to choose because now she has created an awkward pause in the relationship until another conversation is had in the future that now must be initiated by her. And, let’s be honest, she will not be excited about initiating that conversation, will likely avoid it, and the man will be left hanging. Not cool.). However, if she is interested, she could reply like this:

“Bob, thank you so much for telling me where you stand in this relationship. You have made me feel so secure in the way you have approached me these past several weeks and it has made dating you a pleasure. I would would be very interested in continuing this relationship.”

Once the couple has reached an agreement that they are both still interested in continuing the relationship, then the man should begin the process of further defining the relationship by saying something like: “Great. Well, then I thought we could spend the rest of our time tonight discussing what the next stage of our relationship could look like.”

We’ll stop here for now and continue with that conversation in part 2.

Every relationship is different, so it is important to remember that these time tables and methods are completely flexible to the unique nature of each couple. What is most important is that the man is initiating definition with the woman and giving her the opportunity to follow his lead in the relationship or politely communicate to him that she is no longer interested.


Women, is this right? How would you feel if a guy took the time to do this?

Men, how does this strike you? Do you think it’s important to take the time to do this on a regular basis?