Dear Johnathon:
Thank you for your courageous question.
Before answering your question, let me make a couple points about the nature of "dating" itself.
A couple of years ago I heard on "Focus on the Family" a young man of about 22 years of age said one of the most courageous things I have ever head a young man say in this day and age.
He said that he had given up dating because he was not ready for marriage. He explained that the purpose of dating was to find a person for possible marriage and for NO OTHER REASON. Thus, if a person is not ready to marry then they shouldn't date.
Although you are talking about "courtship" I wanted to make that point because so many people, almost everyone, seems to date for the wrong reasons. Dating is NOT for companionship, for sex, to stave off loneliness, or whatever. Dating has one sole purpose -- to seek out a potential marriage partner.
The old convention of courtship went something like this (with variations from culture to culture of course):
1) Dating several people to see the potential
2) Keeping Company with a few people selected from those one dated.
3) Going Steady by selecting just one person whom one feels is a good candidate for marriage.
4) Giving Promises for possible marriage once the relationship has matured to a point where marriage potential is very real
5) Engagement for marriage in which a promise of marriage is made and plans set for marriage.
6) Marriage
This is similar to the process of becoming a Religious.
1) Looking around for a Religious Order = Dating
2) Aspirant = Keeping Company
3) Postulant = Going Steady
4) Novice = Giving Promises
5) Temporary Profession = Engagement
6) Perpetual Profession = Marriage
The point is that marriage as in the Sacrament of Marriage, or as in the spiritual marriage of Religious Vows, is a process of discovery and formation and maturity before the final commitment.
Dating is the first step in seeking a marriage partner. if one is not ready to marry, then do not date, for any person we date is a person we might marry.
In addition, if we date we may find ourselves with feelings of love, including sexual feelings, that we cannot even begin to realize because we are not ready to marry. Thus, again, do not date, unless one is looking for a marriage partner.
Now with all that said, to your specific question.
All physical demonstrations of love that involve nudity or partial nudity or private parts need to be restricted to the marital embrace. To engage in "petting" is like standing in a barrel of gasoline smoking a cigarette; it is stupid and one is asking for it.
We have a moral obligation to avoid even the near occasion of sin. "Making out" as in caressing of private parts and deep kissing is a near occasion of sin that is asking for trouble. The sexual passions are strong. Do not smoke in a barrel of gasoline.
What is okay, in terms of prudence and good virtue, is simple hugging, holding hands, simple kissing, cuddling on the porch swing; that sort of thing. Anything more involved in that is placing oneself in the near occasion of the sin lust and perhaps fornication. Even if not fornicating, one violates the virtues of modesty, prudence, and self-discipline. To violate these virtues is NOT love, but lust; and lust is a sin.
Bottomline: to avoid sin and the near occasion of sin (whether it be the sin of lust or that of fornication or anything in between), do not get the cart before the horse -- keep it simple and lovingly modest -- hugging, holding hands, simple kissing, cuddling on the porch swing. God will bless you both for your virtue.
If this person is for you and your relationship matures and develops til you eventually get married, then you can enjoy each other in the fullness of the marital embrace as a gift to each other; but do not open the gift, or even take a peek, before Christmas...
God Bless,
Bro. Ignatius Mary