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It's Jess' first Valentine's Day as a single woman in six years so she wants to go out and have a one night stand. Schmidt and CeCe agree to be wingmen for her. At the bar, Jess meets Oliver (Ryan Kwanten) and decides he's perfect for her Valentine's fling. Jess convinces Schmidt to drive her and Olver to Oliver's place. Schmidt overstays his welcome, so CeCe comes to pick him up with her boyfriend in tow. Oliver's ex bursts in on the gang and is very angry with Oliver. To get back at him, she starts making out with CeCe's boyfriend, who is high on shrooms so he doesn't protest. Schmidt, CeCe, and her bf eventually manage to leave and Jess and Oliver get down to it. But with Oliver's ex hovering around them, Jess can't go through with it and she leaves.
Nick and Julia have big plans for their first Valentine's Day together, but Julia's demanding job gets in the way. Nick ends up spending most of the night with Julai's intern Cliff. After sharing some of his life stories with Cliff, Nick manages to disillusion Cliff. The intern quits leaving Julia stuck with much more work. To try and help out, Nick does the paperwork, but he does it all wrong. Julia is still grateful.
Winston heads to Shelby's planning to spend a romantic night in only to find out that she's having a girl's night. He decides to stick it out and spends the night with her and her friends. At the end of the night, he gets a Valentine's kiss for his efforts.
When Jess arrives home from her failed one night stand, she thinks about hooking up with Schmidt. Luckily, Nick drags her away or Jess would have walked in on Schmidt and CeCe. The next morning Jess calls CeCe to confess that she almost got with Schmidt, and CeCe looks like she regrets her decision of spending the night with him.