Tomorrow we enter the month of sweethearts and valentines and I thought this mailbag question was perfect for the occasion. Thank you for sending it over Macy!

A friend and I are working on a book and we are having trouble developing a love story between two of the main characters. They are already good friends, but we’re trying to make it more than just friends without it being awkward. Do you have any tips?

First of all, I say embrace the awkward! And I’m not the only one who thinks so. While working on this post, I scrolled a handful of sites and it seems to be the consensus that “awkward” is an important, and very natural step, as two people transition from friends to something more.

There’s an old episode of the TV show FRIENDS that always makes me giggle. After pining for Rachel for years, Ross is finally leaving the friend zone and entering the “something more” zone. The problem is that Rachel can’t stop giggling.

When he asks her why she thinks it’s all so funny, she says, “I’m sorry. I guess I’m just nervous. I mean, it’s you, you know? It’s us. I mean, we’re crossing that line. Sort of a big thing.”

Keeping this line in mind is helpful when you’re working to draw friends together. Crossing over into the “something more” zone can happen in a lot of different ways, but at some point your characters will realize that things are changing. Awkward is a very natural reaction to such a big emotional bombshell.

It’s important to remember that awkward can have a lot of incarnations. There’s cutesy awkward, avoidance awkward, dreamy awkward, angry awkward, confused awkward, clumsy awkward, and plenty more. However your characters are constructed, some form of awkwardness would likely be appropriate when a new feeling is introduced into a friendship.

Some other things to consider:

Show us their friendship. Readers need a good dose of what these two characters look like as friends before they can invest in and appreciate the transition to something more. Put your characters in situations that show us how loyal they are to one another, how dependent, how generous, how helpful, how encouraging, or how infuriating (if that’s how their friendship flies).

Readers need to see their friendship in action because it sets the stakes. When we see how great they are as friends, how valuable they are to one another in those roles, we start to understand what they risk by crossing the line.

Show us why each character is loveable. No, your characters shouldn’t be perfect. Yes, they should make mistakes and have flaws. But you need to orchestrate scenes that show off just why one character is falling for the other and vice versa. What is it that is attractive to the other party? And while physical attraction often plays a role, you need to dig deeper than that if you want readers to buy in.

Show individuality. While your characters may be approaching a line of demarcation in their relationship, they don’t necessarily have to approach the line at the same speed or with the same feelings on the matter.

Perhaps one party is excited about their new-found feelings while the other hates that things are changing. Or perhaps there are situations that prohibit one or the other from acting on their romantic inclinations. However you do it, it’s helpful to remember that these are two distinct individuals, not simply a plot point to wrap up. Let their unique personalities drop obstacles in their path. Obstacles are the storyteller’s best friend after all.

Show restraint. Readers like to feel. In fact, that’s probably why they’re reading your book. If you forego showing off the friendship, setting the stakes, and earning loveability just to jump into the dreamier moments, the payoff will be shortchanged. Let your readers feel each step as the friendship transforms. This increases tension and keeps us flipping pages.

And that’s what every author wants: readers who flip pages.

Tell me, what are your favorite fictional love stories? Do you have any tips for writing a friends to valentines kind of tale?

Shannon Dittemore is an author and speaker. Her books include the Angel Eyes trilogy, a supernatural foray into the realm of angels and demons, as well as the fantastical adventure novel Winter, White and Wicked. Its sequel, Rebel, Brave and Brutal is due out January 10, 2023.

Shannon’s stories feature strong female leads grappling with fear and faith as they venture into the wilds of the unknown. She’s often wondered if she’s writing her own quest for bravery again and again.

It’s a choice she values highly. Bravery. And she’s never more inspired than when young people ball up their fist and punch fear in the face.

To that end, Shannon takes great joy in working with young writers, both in person and online at Go Teen Writers, an instructional blog recognized by Writer’s Digest four years running as a “101 Best Websites for Writers” selection.

For more about Shannon and her books, please visit her website, Instagram, Facebook, Twitter, and Pinterest.