Let a guy buy her a drink: tick
Try something new: tick
Hook-up with someone: ... not quite

For one night only, Naya's friends convince her to shed her frumpy cardigan for an evening on the town. For once, she'll forget about her demanding job and, with the help of her new to-do list, practice flirting with a charming stranger...

Jake might be just what Naya never knew she was looking for. He's sexy, he makes her laugh and he challenges Naya to rebuild her lost confidence.

But the best things in life are never easy, and the complicated strings around dating Jake might just destroy her career. Naya has two options: she can protect her professional reputation and return to her old life, or she can flirt with the unknown and stay with the person who makes her feel like she's finally living again...