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.