This story assumes that Data and Jenna D'Sora's relationship described in the episode "In Theory" happened to coincide with Valentine's Day.
February 11th
Data sat at the Ops console in the front of the bridge, pale fingers flying over the touch-sensitive panel. He adjusted the continuous scan of the space warping past the Enterprise-D and read with inhuman speed some of the more interesting information lighting up his console. Of course, if something of great interest were to make its presence known, the console would make sure the person—or android—at Ops were to notice it. But, Data tended to have a fancy for details and a ravenous curiosity, and this occasion was no exception.
As Data's golden eyes flickered over the console, positrons in his cranium undoubtedly blinking and whirring at the incoming data stream, his advanced hearing allowed him to perceive a shuffling behind him. Data slightly tilted his head to the side, amplifying the sound and therefore giving more clarification to the curious noise. He flickered his eyes to the left before looking back at the black console in front of him. That brief glance allowed his peripheral vision to view the dark red and black uniform and the larger shape of Commander Riker coming up behind him.
Commander Riker placed his right boot on the supporting arm of Data's console, and leaned over. "Have you got anything special planned for Jenna? You know, for the big day?" he asked.
"'Big Day?'" Data asked, confused at the term. Data had noticed over time that humans had a tendency to use colloquialisms, most of which rendered him clueless.
"Valentine's Day?" Riker clarified. "An Earth holiday in February…?"
"Ah," Data said. "I have observed the increase in amorous behavior on this day, especially during my time at Starfleet Academy." Data's eyes seemed to glaze over with the memories, no doubt because his recollections took up all of his concentration considering he remembered every detail of everything said and done.
Riker recognized the signs of one of Data's endless one-sided discussions about to begin, so he quickly put a stop to it before it started, saying, "So, what do you have planned for Jenna?"
Jenna D'Sora was—one could say—Data's girlfriend. After breaking up with her late boyfriend Jeff, Jenna had displayed a new interest in Lieutenant-Commander Data. Data, having no emotions of his own, hadn't noticed the signs until she had impulsively kissed him in the torpedo bay. After that, Data had decided to go with the flow and accepted her growing emotions for him. To satisfy her needs in the relationship, Data had created a sub-routine specifically for Jenna, but he hadn't tried the program yet. So far, the couple was—despite some awkward moments and confusions—currently continuing their time as a couple.
Riker's comment brought the android back to the question at hand and, while simultaneously scanning the contents on his console and contemplating the usage of literary devices in the first chapter of Oscar Wilde's The Picture of Dorian Gray, he looked up and answered, simply, "I have no plans for Jenna."
This innocent and honest remark made Riker pause for a moment. "You do know how women feel about Valentine's Day, right?" Riker asked the pale skinned android.
"No," Data replied. "My lack of emotions does cause me sometimes to underestimate the influence of emotions over humans."
Riker groaned inwardly for Jenna's sake. "Then we have our work cut out for us, Data."
"'We', sir?" Data asked. As he looked at Commander Riker, Data noticed a small grin spread across the man's face.
"Yes, we. I'm not going to let you feel…experience…the wrath of a woman when she doesn't get her roses and chocolate on February 14th!"