Fiona Montgomery has been in love with Owen since she moved to Shadow Ridge two years ago. The first time she saw him, she knew their bears were meant to be together. Although the infrequent dates were disappointing, she understood his passion for the family business, and didn’t press him to give her more. When Owen promises her a surprise, she thinks he’s finally ready to move their relationship to the next level, until she meets the new Mrs. Chocolate. Owen Waverly never minded making sacrifices in his personal life, or working long hours, until his curvy mate walked into his store for the first time. Suddenly, he wanted more than a prosperous business; he also wanted a wife and a family. The internal struggle plagued him until he realized he wanted one more than the other. Determined not to spend Valentine’s Day alone, Fiona contacts the Matchmaker for a date and escapes to her hometown of Shadow Creek. Owen follows, but as the big day approaches, he realizes he might not find Fiona in time. Sometimes a bear in love needs a little help, a little luck, and a whole lot of determination.

Caleb Montgomery has been in love with his roommate forever, but has kept silent out of fear. He’d agreed to a sexual relationship, in the hopes that she’d change her mind, but she never did. On the eve of Valentine’s Day, he decides he can no longer live in silence, and plans to tell her the truth on the day of love. Tall, curvy, Marianne Harris has always known she wasn’t Caleb’s type, but when he offered her a friend’s with benefits relationship, she couldn’t say no. The approach of Valentine’s Day reminds her of how they met, and what her fate will be when Caleb finds the one. When Caleb finds out Marianne contacted the Matchmaker for a date, anger and jealousy replace his fear and he lets her go without a fight. Marianne knows she must take drastic measures, or she’ll never be able to move on, but her heart aches for her bear. When two bears who love each other keep silent, the Matchmaker steps in and helps a bear in trouble.

Cecelia “CeCe” Clark is lucky in business, but unlucky in love. She found her mate more than a year ago, but quickly learned that fate had made a mistake. Her curvy body, and comfortable, casual style don’t fit into her mate’s luxurious, suit-wearing world, and even if they did, he was already taken. Ian Walker knows his gorgeous mate doesn’t like him, but he has no idea why. One day they were flirting, and slowing getting to know one another, and the next, everything changed. They were both to blame, but he had no idea how to mend the rift between them. With Valentine’s Day fast approaching, the Matchmaker has a few plans of her own, and when CeCe ends up owing the woman a favor, all bets are off. Sometimes, the only way to help a bear in denial is to isolate her with the truth.