LGBT, Contemporary Rose Winters made a bet with her lover that she can get three relationships together and prove to him that she can be the next drag queen Dear Abby. It's a gamble but she's going to get Neo and Phil together and isn't afraid to play dirty to do it. Phil was once Neo's dream of a guy but then he took off the morning after their one night stand. Unlike other guys, Neo wasn't sure he wanted temporary with Phil, but that's what it turned into. He's determined he won't give Phil the chance to hurt him again. Phil had just tiptoed out his sexuality when he and Neo had a night, but problems in his family led him to shove it back in the closet, leaving Neo in the dust. Phil regrets the past but knows he'll never make it up to an angry Neo. Until Rose steps in. But can Rose's gamble tip them back into a relationship, or will the same factors that tore them apart to begin with rear their ugly heads again?

Rose Winter helped one relationship get together but now she has her work cut out for her. This time, it's personal. Tucker and Ally have been Devyn, Rose's alter ego's, friends since college. And they've had a torch burning for each other all along. Now, the flame's in danger of sputtering out. Their friends with benefits relationship doesn't work for Ally anymore. She wants more, but knows commitment-phobic Tucker can't man up. At least until not until Devyn dares him to make it work. And Tucker dares Devyn to help him. With a plan that includes strip poker, a hot tub, a night never to be forgotten, it looks like Rose, that is Devyn's, sure to book another win. But can Ally and Tucker take the final plunge and make friends-with-bennies into forever?

Rose Winter has brought two relationship together. But now she has her greatest challenge yet. A threesome. But will she risk her own relationship to make this difficult match? Josie’s not a bad person. She’s just dating two guys. Really hot, sexy guys. She’s been honest, but now it’s time to tell them about her lack of a decision as to which guy to keep dating. Only much to her surprise, Quinn and Zach don’t want her to choose. They not only find her sexy, but are attracted to each other too. Although the idea intrigues her, Josie's s a good girl looking for Mr. Right, not Mr. Right and Mr. Right #2. Zach doesn’t believe he can ever find happiness. He doesn’t dare dream about the relationship he needs actually working—no matter how much he desires both Josie and Quinn. And Quinn’s determined he’s going to win them both over and try something new. It’s going to take everything he has and more to get the two of them onboard. With Rose’s behind-the-scenes guidance, will they take the risk of being together?