Don't Start What You Can't Finish

Having done a lot of ministry and given numerous talks to teens the question of "how far is too far" often comes up when discussing relationships, chastity and purity, and femininity and masculinity. This summer I spoke with my Totus Tuus teammate, Katherine, about the question in great lengths because I found myself stumbling for an answer. Well the truth is, as many chastity speakers have said, purity is not about how far can you go but how high can you aim. Better questions to ask yourself are: how much can we glorify God in this relationship? How can we lead one another to sainthood? How pure can we be (what is purity?)? How can we love one another with Christ's love?
I would have to argue that a relationship that isn't searching to answer these better questions is going to have a really hard time being chaste. I know personally in my own relationship once Jake and I started discussing the value of purity in our relationship and very intentionally turning our relationship to God through the hands of Our Lady that the "how far is too far" question wasn't about what is sinful and whats not but how can I respect and honor you as totally belonging to God and how can I help you be a saint.
Nonetheless it is a good thing to know and ask. I say this because we like concrete rules to understand virtues. we like our actions to define our hearts. Often we hear opinions of how to act in a pure relationship. Some say don't kiss until you're married. Some say just don't have sex and do whatever else you want.
I would say that the question needs to be asked not so much as to see how far you can go in order to be morally stable while getting the satisfaction you desire (which just doesn't make sense because you start making God's laws abide by you and your desires) but rather a relationship needs to be focused on one another's ultimate purpose and calling - to be holy, to be saints. The question then becomes what are we doing that is drawing us from Christ-like virtue? and what is it that we are doing that is appropriate in the face of God and leading us to sainthood?
To be practical and satisfy this "how far is too far" question, I would say: Don't start what you cannot finish.
Before Marriage we do not have the Sacramental Grace to love in the way sex calls for. Simply, we cannot be total self gifts if we are not vowed to one another for a life long commitment. So why even try to go down that road? If the actions that you perform with your boyfriend or girlfriend get you ready for something you are not able to do than that's too far.
This is a hard thing to do. "Well we were just kissing and then that led to more and then and then..."
I would say recognize in your own heart and in your relationship where you cannot go without it getting you ready for sex. Practice self control. Sacrifice your desires for the sake of the purity of your boyfriend or girlfriend. That is true love: willing the will of God for that person.
Also just to point out - there are certainly inappropriate actions that should be avoided in a relationship before marriage. These actions would be equivalent to touching fire to see if its hot (which is just unnecessary, we can all agree? we know fire is hot, so why test it?) I'm not just saying make your own rules but I'm challenging you to recognize the dignity that sex has in a marriage and its misplacement outside of a marriage and to truly love one another in such a way that makes you pure of heart and body and on the way to becoming saints, not on the way to doing something you cannot yet do. So don't start something you can't finish - don't get to that point.
If you happen to have pushed the envelop a little far or maybe if you've already had sex outside of marriage, its okay. Seek the Lord's forgiveness and healing that he longs to give you and ask for his Grace. Ask for the prayers of the holy saints who sacrificed so much for a life of purity. You were made for more than your mistakes and in God's eyes you are still infinitely loved so seek his compassion and his everlasting love and try again. Jake and I aren't perfect but we constantly refocus our relationship to God and try again.
Psalm 37:23-24 "Those whose steps are guided by the Lord, whose way God approves,
May stumble, but they will never fall, for the Lord holds their hands"

St. Thomas Aquinas, pray for us
St. Maria Goretti, pray for us
St. Joseph, pray for us
Jesus, Purity of virgins, have mercy on us.