Boundaries/Dating/My Relationships/Teen Relationships

7 Questions to Ask Yourself When Asking: How Far is Too Far?

Enquiring minds need to know: what is the virtuous, unmarried Catholic man or woman to do, when they like someone and want to show it? Sexual desires are a normal, healthy part of being human, right? So if chastity is about respect for sex and our sexuality – and there’s a lot of stuff you can do, without doing it – then how far is too far, exactly?

It’s going to take a lot more than 140 characters to answer this. In fact, it takes seven other questions:

1. How well am I living chastity in general?

Chastity is about more than just the purity of our bodies – it’s about purity of our bodies, hearts, minds, and souls. If someone struggles with pornography, for example, his/her perception of what is and isn’t acceptable in a romantic relationship will be twisted. That person will need help (Confession and accountability partners, for sure; perhaps spiritual direction and/or therapy, depending on the amount of exposure) rewiring his or her brain to a healthy sexual place before dating someone – whereas someone without that struggle could go on a date, no problem. Before entering into a romantic relationship, have a clear understanding of what the virtue of chastity is, commit to living it your whole life long, and do your best to live it on your own.

2. Where are we?

If you’re not in a relationship, then ‘How Far Is Too Far?’ is a conversation for a different day. I knew a woman in her 20s who was absolutely committed to saving sex for marriage (which is fantastic!), but had no problem making out with a different guy every weekend (which is not so great). Chastity is not just about abstinence, and physical affection should be reserved to relationships. Otherwise, it’s just use. Also make sure, within your relationships, that the physical affection develops slowly. The other areas of the relationship (emotional, intellectual, spiritual) should always develop ahead of the physical. With greater commitment, comes greater intimacy – so since marriage is a place of total commitment, it’s the only appropriate place for total intimacy.

Secondly, where are you – location-wise? There are some places where things can be more tempting than others… Avoid basements, bedrooms, and backseats and have your private time in a public place. It’s a lot harder to push things too far, physically, when you spend the evening hanging out at a greasy 24-hour diner, and your goodnight kiss happens standing outside the car in their well-lit parking lot, right? Choose your location wisely to set yourself up for success.

3. Does this create a desire in me to do more?

Part of living chastity is being self-aware, so this is one of those gray areas that I can’t answer for you. Depending on a multitude of factors (sexual history, exposure to pornography, level of commitment to chastity, etc.), what’s very tempting for one person may not be tempting to someone else. Regardless of our circumstances, one thing is created to lead to another, and it’s unhealthy to amp things up physically and then cut them off – that can lead to repression, which will make it more difficult to give of ourselves freely within marriage. Ask yourself: does ___ action creating a desire in me to go further? If we do __, will it stimulate one or both of us sexually? If so, it’s too far for you. By knowing yourself well, you can discern for yourself ‘how far is too far?’ before you ever reach that point.

4. Does this create a desire in the other person to do more?

Similarly, the person you’re dating should also be committed to living the virtue of chastity and have their own awareness of what is too far for them. Hypothetically, let’s say that a guy with no sexual baggage dates a girl who had a sexual relationship in the past. They’re both committed to chastity and begin dating. She knows that making out will tempt her to go further; he thinks extensive kissing won’t be an issue. Where should they draw the line? They should, out of love and respect for one another, cut off prolonged kissing before it gets to making out. It would be disrespectful to take things to a place that will frustrate one person, even if the other person would be fine. Clear and open communication about boundaries is essential.

5. Is this affectionate or lustful?

It’s healthy, right, and just to show affection to people we love. Consider our friendships, or family relationships – so much love can be communicated by a hug, a handshake, a pat on the back. In our dating relationships, affection can and should look a little different (provided that’s healthy for both parties in the relationship) because a romantic relationship should be different from any other friendship. Holding hands, walking arm-in-arm, a kiss on the cheek or the mouth means something with a boyfriend or girlfriend. So be aware of what you’re communicating: affection seeks to give love to the other, whereas lust seeks to take pleasure for itself. Are your actions motivated by what feels good for you, or what affection you desire to give?

6. Am I crossing lines that shouldn’t be crossed?

There are definite no’s outside of marriage. Our bodies speak a language, and the message of sex is ‘I give my full self to you, and you alone, forever.’ If two people haven’t committed to marriage, then they aren’t capable of making that statement – and any body language that says otherwise is lustful. So, outside of marriage, while it’s impossible to draw any one line that is true for all relationships, there are some things that are definitely inappropriate for all non-married relationships. Biblically, there isn’t any talk of ‘dating’ or ‘engagement,’ there’s only married or not – so until someone is a spouse, he or she is a brother or sister in the Lord, and needs to be treated with purity. That means everyone should remain fully clothed at all times, hands shouldn’t wander to places swimsuits cover up, and if it says ‘sex’ in the title of the act, it isn’t chastity. If things have gotten too physical in the past, make use of the Sacrament of Reconciliation. Not only will you receive forgiveness for past mistakes, but also grace to do better in the future.

7. How can I best love this person?

True love wills the good of the other (St. Thomas Aquinas said that, and he’s a doctor of the Church) – so every action within your relationship should be oriented toward the other person’s ultimate good: holiness. There are so many awesome, fun, creative ways to show your boyfriend or girlfriend that you care about them that won’t lead you to a confessional. For a healthy and well-rounded relationship, show your emotional, intellectual, and spiritual affection as best you can. Plan creative dates. Have great conversations. Pray for one another. And embrace the virtue of chastity – it’s the best way to love and respect the whole person – body, heart, mind, and soul.


Do you have a question about dating and relationships you’d like to ask David and Rachel Leininger? Email them at and your question could be the next blog post!


About the Author

Rachel Leininger

I work for a retreat ministry called the REAP Team, where it's my full-time job to talk about sex, love, dating, and chastity (which can sometimes lead to some awesomely awkward moments). I love being Catholic, my bearded husband, watching movies, and browsing antique malls. The only thing I have against winter is the fact that there's no baseball. Follow me on Twitter and Instagram @raleininger

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