Tara Winters will never forget that fateful day back in high school when, in her haste to get to class, she barreled into a boy with the brightest blue eyes she’d ever seen. She was mortified to discover that it was none other than D. J. Parker: popular senior, soccer star, and way out of her league. Yet when he was assigned as her study hall leader, the two formed an unlikely friendship. Tara always hoped their relationship could be something more and dared to believe it was possible after they shared a spectacular kiss. But when D. J. confronted her about it, she said that the kiss hadn’t meant anything, when in fact, it meant everything. But how could she admit her true feelings when he was a popular, accomplished, and very spoken-for senior, and she a mere freshman with less-than-stellar credentials? The decision has haunted her ever since, so she vowed to never let a chance at love slip by again, even if that meant saying yes to any dating opportunity that came her way.
Now in her midtwenties, Tara has become quite the dating expert with a constant stream of suitors. But none measure up to D. J., her first true love. Tara blogs about her dating escapades and has amassed quite a following—perfect strangers invested in her finding “happily ever after.” While she’s seen as the quintessential singleton, all Tara wants is to settle down. She leans on her best friend, Andy, for advice and support throughout her dating debacles. She’s beginning to seriously consider his proposal from that drunken night where they vowed to marry if neither has settled down by the time they’re thirty. Then Andy meets Natalie, a high-strung Pilates fanatic who is of the mind-set that men and women cannot be friends. As Tara finds herself competing for her best friend’s affection, she must decide if she’s in it for the right reasons—or simply to win. Because she still can’t seem to put the ghost of D. J. behind her. Along her journey of self-discovery, Tara shares pieces of dating advice with her followers. But perhaps the most important lesson she must learn is to embrace the power of “no” to find her happy ending.
I Should Have Said Yes is a refreshing, candid, and often humorous look at what it takes to find Mr. Right.