Want Better Friends? Start With These Ancient Approaches from 44 BC

Friendship has always been at the heart of a woman’s life. The ancient Greeks called it “philia”: the love of shared virtue, mutual encouragement, and delight in another’s presence. The Romans, through voices like Cicero, gave us some of the most enduring wisdom on what friendship ought to be. In How to Be a Friend, written in 44 BC, Cicero shares his journey of friendship filled with timeless advice and insights that insist that friendship cannot be based merely on utility or pleasure, but it must be rooted in virtue and goodness.

This classical foundation shines a light on the struggle many women face today. Making friends as an adult feels eerily like dating… You meet someone new, sense the possibility of connection, and then wonder if this will be your best friend for life, or if you will slowly drift apart.

The classically feminine approach doesn’t avoid this reality, but looks deeper.

On a search for your “kindred spirit” in the words of Anne Shirley, you sometimes find a friendship that develops beautifully. Other times, you realize you’re not as aligned as you thought. The parallels to dating are uncanny, and if we don’t approach this season of friendship-building with intentionality, we can end up either isolated or surrounded by relationships that quietly drain us.

Classical femininity offers us a refreshing way forward with a differing perspective from modern approaches. Our differing approach to life does not promise effortless bonds, but it does give us the tools to cultivate friendships that are truly nourishing, marked by Truth, goodness, and beauty.

Why Friendship Feels Like Dating Today

The shift away from built-in friendships is cultural. As we live in a transient age, where neighbors may only stay a year, careers uproot families, and online communities often replace local gatherings, we add to this the busyness of adulthood—work, family, commitments—and you have a recipe for scarcity. Growing up, we stumbled into friendships just by playing outside or sitting next to each other in homeroom.

These days, friendships require the same level of pursuit, discernment, and even “chemistry” that dating does. The question isn’t only: Do I enjoy this person? But also: Do we share values and a vision for life that allows us to walk together?

Cicero observed that friendships formed out of advantage alone rarely last. We see this now more than ever. People often treat friendships transactionally, like networking for career gain, gaining a companion for status, or clinging to relationships out of convenience. This is why the process of “vetting” feels so much like dating, as you’re seeking not just someone fun, but someone whose soul aligns with yours in friendship.

Step One: No Desperation

The first step is determining where you are coming from. A woman who is at peace with herself doesn’t cling to friendships out of fear of loneliness. Instead, she opens her life with generosity and warmth, believing that she is worthy of high-quality friendships. 

Desperation for a friend often leads to poor choices like investing in them too quickly, excusing red flags, or forcing intimacy that isn’t there. Just as we often talk about these things in dating, the same issues must be considered with friendships. Classical femininity trains us to be content in our solitude so that our friendships come from abundance, not lack. Cultivate your home, your rituals, your sense of beauty, so when your life is already rich, you won’t need friends to fill a void but to share in the joy.

Here, Cicero is instructive on this topic by writing that true friendship can only exist between people who are “good” in the moral sense. This doesn’t mean they are “perfect,” but it does mean you must be striving toward virtue yourself if you hope to find virtuous companions. In other words, the work begins within. When your own life is marked by integrity, you will naturally attract others walking the same path.

Step Two: Vet Early and Kindly

This is where friendship begins to mirror dating most clearly, and we must properly learn the art of vetting. It’s important not to approach this step with suspicion or cold judgment, but with attentive discernment.

Pay attention to how your potential friend speaks:

• Does she gossip about others freely?

• Does she complain endlessly without gratitude?

• Does she show respect for her family, her commitments, and herself?

  
  

A woman’s words are a window into her heart, and if you listen closely, you’ll know whether she is someone who builds or someone who tears down. If she’s speaking poorly about someone else, she likely will do the same for you down the road.

Vetting may seem forward and unkind, but it really is not. In fact, it’s deeply kind to yourself and to her. By recognizing incompatibility early, you save both of you from the strain of a mismatched friendship. Cicero warns against false friends who flatter, manipulate, or lack constancy by reminding us that “friendship is nothing unless it is steadfast.” In the modern context, that means paying attention to early signs: is she the type who shows up in both celebration and hardship? Or does she vanish when life gets difficult?

To vet kindly is not to judge harshly, but to take Cicero’s wisdom seriously that friendship is too precious to be wasted on those who are faithless.

Step Three: Look for Shared Rhythms

Compatibility is not about being the same in beliefs, habits, or style, but about shared rhythms of life. If you love lingering Sunday dinners, is she someone who values gathering over a meal? If you’re committed to orderly habits and purposeful work, can she respect that, or does she constantly pull you into chaos?

Friendship is lived out in ordinary moments, and two women can admire each other but never become close simply because their lifestyles don’t overlap. When rhythms align—whether through shared traditions, hobbies, or even similar seasons of life—friendship has fertile ground to grow. This is why you had so many friends in school growing up, or at your work, or with other mom friends.

Here we might apply Cicero’s idea that friendship is “a complete harmony in all matters human and divine, joined with mutual goodwill and affection.” Harmony doesn’t mean being identical; it means two lives moving in sync. A classically feminine woman notices whether another’s rhythms are compatible with her own, as there is no hard striving to make it fit or find similarities.

Step Four: Start with Small Invitations

As easy as it might be to dive into deep vulnerability on day one, maybe think twice before sharing your life story. Instead, extend small invitations like coffee at a local café, or maybe a walk in the park, and perhaps a casual errand together. Small commitments like these are, in a sense, crude as it might sound, a test.

Does she show up on time? Does she reciprocate by inviting you into her world? Does she listen as much as she speaks?

Little things, even though there might be excuses, reveal much. If she consistently cancels, never initiates, or treats your time as disposable, believe her actions. Conversely, if she responds with eagerness and follow-through, you’ve discovered someone worth considering more seriously as friend material.

Cicero believed friendship develops best over time, tested by constancy. Small gestures like keeping a coffee date, remembering details, and even simply offering encouragement become the proof that a person is who she says she is. The early stages of friendship are less about trying to impress a potential friend and more about discerning who they really are.

Step Five: Guard the Gate, but Keep It Beautiful

Modern culture has been positively bullish on the need for friendship to require boundaries. But still, too many women either open their lives too widely and let anyone in or shut themselves off completely, for fear of disappointment. The classically feminine way is balance.

Cicero cautioned against indiscriminate intimacy. While it is good to be friendly with many, only a few should be admitted into the deepest circle of trust. In his words: “When a friend asks something that is not right, one should not grant it, for friendship is a partnership in virtue, not in vice.” The classically feminine approach echoes this: guard your circle, but let it radiate beauty so that the right companions feel welcomed in.

Common Mistakes in Modern Friendship

Here are a few traps many women fall into:

1. Confusing Proximity with Compatibility. Just because you work together or attend the same church doesn’t mean you’re meant to be close friends.

2. Mistaking Fun for Depth. Someone you’ve just met may be delightful at brunch, but then absent in a crisis. Friendship is proven in difficulty, not just the fun times.

3. Ignoring Red Flags If she regularly mocks her spouse, belittles her children, or dismisses her obligations, take note. These patterns often will come back to haunt you.

4. Forcing Intimacy Too Quickly. Oversharing on day one can create a false sense of closeness that rarely lasts. Depth takes time.

How Can We Get Better at This?

Friendship is an art that improves with practice, and the more you step out, the sharper your intuition becomes. You learn to read character, to recognize generosity, and to value consistency. Cicero’s central teaching is liberating on this topic: friendship is only as secure as the virtue it rests upon. If a friend asks you to betray your conscience, she is not truly your friend. If she encourages what is noble, uplifts your character, and steadies your heart, she is worth every investment of time and affection.

Here are three ways to grow in this art:

1. Be a Woman of Follow-Through. Show up when you say you will. Send the text. Write the thank-you note. If you’re reliable, you set the expectation and she should reflect that as well.

2. Embrace Seasonal Friendships. Not every friendship is forever. Some last a season, and that’s beautiful and totally fine. It’s perfectly normal to have different types of friends in different seasons and at different arm's length. They likely each taught you something at the differing stages in your life.

3. Seek Virtue, Not Just Affection A true friend doesn’t just make you feel good but ultimately makes you a better woman. Look for women who inspire you to grow in what is True, good, and beautiful. If, in time, they provide you with constructive criticism, listen to them

A Checklist for Vetting Friendships

Drawing from Cicero’s wisdom, ask yourself:

• Does she love Truth, even when it’s difficult?

• Is she steadfast in word and action?

• Does she uplift virtue or pull me toward compromise?

• Is our relationship built on shared values, not convenience?

• Does her presence make me more courageous, more hopeful… more good?

Cicero concludes his work by sharing that “friendship improves happiness and abates misery, by the doubling of our joy and the dividing of our grief.” That, at its heart, is why we continue the sometimes awkward, sometimes painful process of seeking true friends. Because what lies on the other side is not just companionship but a shared life that multiplies goodness.

Classically feminine women do not pursue friends casually. Instead, we stand rooted in a long tradition that stretches from Cicero to our own dining room tables, of women who believe friendship is one of the greatest treasures we will ever be given.

If you are looking for a place to find like-minded women to befriend, our mission at The Swish is to help you foster that community! Stay tuned for more to come soon.