The "DTR" (Define The Relationship) is a very controversial, and I believe misunderstood, concept. Many people are very averse to it, and never recommend it to be done under any circumstances and instead that clarity should come about through other parties (i.e. talking to others in order to have them relay information on your behalf, etc.). I, however, have a different opinion on the matter. I believe the DTR, while it can be awkward and even mishandled, can provide many benefits to clarifying together an often confusing and hard to navigate process of dating/courting that leads to marriage. I also believe that it can help to set up a proper foundation for communication for the future of the relationship, because at some point (i.e. marriage) a couple should not be dependent on others in order to communicate how they feel or what they think, and this usually takes practice.
So when do I need a DTR?
I like this definition and understanding of when the DTR is most needed and most helpful: "It's the imbalance between the evidence of connection and clarity that can create anxiety in a relationship. Someone who feels a strong connection growing with another person but doesn't know his or her status with that person may feel vulnerable and maybe even taken advantage of. When the evidenceof connection greatly exceeds clarity, it's helpful for couples to have a DTR."
Basically, if you start to have anxiety or tension in the relationship caused by wondering where you are at in the relationship and/or where things are going, then it is probably time to have a DTR.
Over the course of a relationship, you will likely need to have more than one DTR. Even in marriage it is good for couples to discuss where they are at in their relationship, where they are going, and what needs to happen to embark together in those directions.
Be careful that you do not push to have the DTR to quickly, otherwise you might 'scare' off the other person or force them to make commitments to soon. For example, the first date is probably not the time to have a DTR.
Also be careful that you are not pushing the DTR inappropriately simply because you are insecure and want to feel safer. There are real insecurities that can come with romance, especially when there is lack of genuine clarity, but we must fight to have our ultimate confidence and security in the Lord and not in the status, or even clarity, of a relationship (Ps 94:22).
So how do I have the DTR?
The DTR can be very awkward and scary, let's face it: you are putting yourself on the line. The basic premise of the DTR is to clarify what might be confusing or ambiguous about the relationship, but you have to be ready and prepared for the clarification to not be what you want. This is especially true in the beginning stages of a relationship. If you are going to try to clarify what the intentions and motives are of the relationship and where things are headed, then you must have the maturity to handle hearing that your desire for the relationship is not reciprocated - this can be quite painful.
*This is the main reason I believe that people are averse to the idea of the DTR, because often people lack the maturity to do it well and thus cause more damage. Therefore, I say that if you are not mature enough to have a DTR, then you aren't really mature enough to pursue a romantic relationship in the first place, it would be better to wait - if you are going to get in the arena of romance, you must be ready to be hurt.
You need to use appropriate language for where the relationship is at.
For example, on the second date, you probably don't want to say something like; "I have really grown very fond of you and in fact I love you and have decided that I would like to make you my spouse, how do you feel about that?" This is inappropriate to the stage of the relationship (unless people are acting out of hyper-emotionalism, or there are extenuating circumstances such as being close friends for an extended period of time before going on dates, etc.). Instead something more appropriate should be communicated along the lines of: "I have really enjoyed our past couple of dates, and getting the opportunity to know you better. I would like to continue to get to know one another and wanted to see how you would feel about us doing that intentionally through talking consistently on the phone once a week and going on some more dates together?"
Perhaps the relationship is much further along and the couple has been dating steady for over a year and wish to have clarity about the future and timeline of the relationship; "I like/love (some people are hypersensitive to the use of that word - an entire DTR around how/when to use that word could possibly arise) you and would like to see our relationship progress to the next level, but I want to make sure that we are able to start out on good foot and have a good situation financially/career/etc. I am getting input from others in my life about this and have some plans in place to help us get there in a timely fashion. How do you feel about that? or perhaps; "I have really enjoyed our relationship over the last year and I am excited to continue to pursue this relationship to see if it can continue to progress toward marriage or not. I would like more time to date and get to know one another before we progress on to the next stage", or perhaps; "we have been dating for a while now and I am not sure that I really foresee our relationship progressing much further, I think it would be best for us to stop pursuing each other romantically."
Should I get help with the DTR?
You should have some trusted spiritual advisors (your tribe) that can help you navigate how and when is best to have DTR's along the development of a relationship. It is good to have some advisors that are married and have gone through this type of process successfully.
While there is no formula to the DTR, or to relationships in general, prayer, wisdom, and selflessness should govern our decisions when it comes to having DTR's, not fulfilling our own selfish needs or desires, and certainly not to fulfill some insecurity that we have.
The DTR can be a very helpful tool, not only to help clarify where the relationship is at and where it is going, but also to help people learn to communicate through feelings and desires in honest and vulnerable ways while at the same time learning to trust God through very scary and emotionally naked times. This helps to set foundational building blocks in one's faith and the relationship that will be needed in the future.
For more on the DTR, as well as an assessment on whether your relationship is a candidate for a DTR; see here.