I get this question a lot by guys in dating relationships or guys who want to be in dating relationships. I wrote a response to this question over at the The Rebelution Forums in the section specifically for men and here was what I had to say:
I am a very black and white man, and I do not believe in compromising for anything or anyone lest you wish to tarnish your core integrity: who you are. Over this past year, I have been serving in ministry as a performer and speaker on several subjects; one of which is purity. It has come to my attention that my previous solution mentioned on the first page of this thread is inadequate in addressing the question.
Firstly, the question should not be, "How far is too far?" The real question you should be asking yourself is, "If I do this, will I be tempted to go further?" Temptation never slaps you in the face, but instead whispers suggestively in your ear. You must do the opposite and never whisper suggestively back, but slap temptation in the face with full armor of God.
I can't tell you where to stop, what action is going too far, except that you know you've crossed the line when you've lost your virginity. If you have any desire to avoid even getting close to that, then please heed my advice.
You as the man must set the boundaries, and once you've come to terms with that you're next step is determining what boundaries those are. This second step requires a lot of honest discussion between you and your significant other; I'd even go so far as to suggest that you may want someone the two of you trust to encourage you to be as brutally honest with each other as you can. If you and your significant other are not completely honest, even at the risk of disagreements and hurt feelings, the boundaries will be set too low and you will fail and maintaining the desired level of purity.
For example, when I choose to enter a relationship, right off the bat I'm going to tell my girlfriend that I am not comfortable being in a dark room alone with her. From there, I will take in to consideration what she is not comfortable with; constantly honing in on what we're comfortable with until we know exactly when to stop before we invite the temptation to sin.
Remember that your goal is not to come up with a list of things you can and cannot do, but to draw a definitive line which you both agree you are not going to cross. If you're definitive line is "not have sex" then you have missed the point of my advice completely and need to go back to the first step. These measures are taken not to just help you both save your virginity, but to also keep you from inviting the temptation. Let me put it allegorically, I'm not just trying to keep you from burning your hand, but to show you how to avoid getting to close to the fire to begin with.
I hope this advice proves insightful to those of you who may not have the answer to the question, "How far is too far?" Hopefully, it will also be insightful to those who do.
Until next time,