Find your Gilbert: Dating tips from Anne of Green Gables

By Erika Ahern

Published on February 10, 2025

Anne Shirley — the spirited, imaginative heroine of the Anne of Green Gables series by L.M. Montgomery — never faced the unique trials of the modern dating scene. But the story of her loathing-turned-love for Gilbert Blythe holds lessons for young women even today.

From the first pages of the first novel, Anne’s longing for beauty and love drives the storytelling. In her imagination, the world takes on an almost sacramental quality (remember the “White Way” and the “bend in the road”?), and friendships are sacred (“my bosom friend”!). 

As Anne grows, so does her appreciation for Gilbert, modern literature’s #1 frenemy.

Whether you’re waiting for your own Gilbert or simply looking for a wholesome perspective on human love, here are eight romance tips inspired by Anne-with-an-e. 

Look for good qualities that complement yours.

“Gilbert would never be Andrew’s ideal of a college hero. Gilbert’s way of doing things might not be Andrew’s way, but he had qualities of greatness that were Andrew’s best ideal made flesh.” (Anne of Avonlea)

Anne initially dismissed Gilbert because he didn’t match her dramatic notions of romance. But over time, she realized how much his steady support, intelligence, and humor complemented her passionate, dreamy nature. Look for someone who balances and enriches your unique personality.

Prepare to be surprised.

“Perhaps, after all, romance did not come into one’s life with pomp and blare, like a gay knight riding down; perhaps it crept to one’s side like an old friend through quiet ways; perhaps it revealed itself in seeming prose, until some sudden shaft of illumination flung athwart its pages betrayed the rhythm and the music, perhaps . . . perhaps . . . love unfolded naturally out of a beautiful friendship, as a golden-hearted rose slipping from its green sheath.” (Anne of Avonlea)

Anne spent years dismissing Gilbert Blythe, looking for a grand, storybook romance. But real love often grows quietly and steadily. Don’t mistake drama for love; look for someone who feels like home.

Love is a decision, not just a feeling.

“It’s not what the world holds for you. It’s what you bring to it.” (Anne of the Island)

In Anne of the Island, Anne falls hard for the wrong guy. Roy Gardner fits the image of the perfect man she had conjured in her dreams – with all her youthful, romantic ideas of a love that sweeps you off your feet. 

“[Anne] lay long awake that night, nor did she wish for sleep. Her waking fancies were more alluring than any vision of dreamland. Had the real Prince come at last? Recalling those glorious dark eyes which had gazed so deeply into her own, Anne was very strongly inclined to think he had.” (Anne of the Island

Anne’s feelings for Roy turn sour, even as her admiration for Gilbert grows. Eventually, she realizes that lifelong love is a decision of both the heart and the head. Feelings may ebb and flow, but integrity, honesty, and responsibility are a more important foundation than a man’s “dark eyes” (Gilbert, of course, has it all).

Learn from your own mistakes (let him help you).

“Isn’t it nice to think that tomorrow is a new day with no mistakes in it yet?” (Anne of Green Gables)

Anne’s life is full of mishaps—dyeing her hair green, breaking her slate over Gilbert’s head—but she always learns and grows from her experiences. In romance, she is endlessly awkward (and even cruel sometimes). 

A man worthy of you is willing to rescue you from your silliest antics without making you feel small. Remember Anne’s attempted re-enactment of the Lady of Shallot? Gilbert offers only a small chuckle (every marriage needs a sense of humor) before rescuing her from the icy waters.

Still waiting for love? Learn to be a great friend.

“True friends are always together in spirit.” (Anne of Green Gables)

Anne and Diana Barry’s friendship was the foundation of Anne’s early life. In romantic relationships, too, friendship is key. Anne is a great friend – and Gilbert notices. He may find her devotion to Diana irksome at times, but he also finds it admirable. 

Anne and Gilbert start off as rivals, then become “chums,” and finally – after her ill-fated sentimental romance with Roy Gardner – a couple. Gilbert earns Anne’s friendship and her hand in marriage.

Choose a man of virtue.

“I wouldn’t want to marry anyone who was wicked, but I think I’d like it if he could be wicked and wouldn’t.” (Anne of the Island)

Anne values someone in control of his own passions who can also acknowledge his mistakes. Gilbert is the first to be gracious in their relationship (“I’m sorry I called you Carrots”). He also challenges her to show that same graciousness to him.

In addition to his virtue, Gilbert could match Anne’s wit and challenge her intellectually. A good husband encourages you to grow and inspires you to be better, while also sharing a sense of fun and adventure.

Be patient.

“All things great are wound up with all things little.” (Anne of Avonlea)

Anne’s love story with Gilbert didn’t happen overnight. It took years of personal growth and mutual understanding before they found their way to each other. 

In fact, Anne rejects Gilbert’s first proposal. 

In the end, however, his patience is rewarded.

“I asked you a question over two years ago, Anne. If I ask it again today will you give me a different answer?”

Still Anne could not speak. But she lifted her eyes, shining with all the love-rapture of countless generations, and looking into his for a moment. He wanted no other answer.

(Anne of the Island)

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C. Holloway
C. Holloway
1 month ago

This is one of the best articles on waiting for the right man that I have read! As someone who is mid-series and did not want to spoil the rest of the Anne books, I did have to skip over a few paragraphs!

Say hi to strangers
Say hi to strangers
1 month ago

Re: Love is not a “feeling”– stop dismissing feelings! Anne noticed how Roy’s lack of shared humor made her “feel” flat towards him, while seeing Gilbert with another woman whipped her feelings up into an ire! You have to be discerning if not motivated by strong movement of the heart in the initial bonding stages of love! St. Ignatius would entirely approve. Unless we are entering arranged marriages, I think we have begun relying too heavily on a strict reading of one single line from JPII.

Say hi to strangers
Say hi to strangers
1 month ago

My man’s “dark eyes” have kept me intoxicated by him for many years…and mine to him! This is a natural part of God’s plan!

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