Despite his charm, Data isn’t without his flaws. Although programmed to adhere to social norms, he frequently breaches them, sometimes resembling that well-meaning but socially awkward friend you hesitate to bring to gatherings. Occasionally, his actions extend beyond mere faux pas into darker territory. A closer look at his tender moments with his pet cat Spot reveals a curious detail: Spot’s gender appears to change without any acknowledgment from Data. This silence from his friends suggests a possibility that Data might have replaced Spot following an unfortunate incident, without anyone noticing.

Data’s questionable behavior isn’t limited to speculative pet-related mishaps. His actions often border on the audacious. Here’s a closer look at some of Data’s most questionable moments, ranked from mildly embarrassing to downright troubling.

Many adults have experienced cringe-worthy moments while under some influence, and Data is no exception. In the episode “Masks,” Data encounters a comet that houses a technologically advanced library dating back 87 million years. After a peculiar light from the comet envelops him, the Enterprise starts to transform into a replica of an ancient temple with Mesoamerican influences, dragging Data along for the ride.

At one point or another, most adults have done something mildly to horrifically cringeworthy while under the influence. That’s exactly what happens to Data in “Masks,” after coming into contact with a comet containing an 87-million-year-old, technologically advanced library. After getting blasted with a funky light while scanning the comet, Enterprise almost immediately begins to change, transforming little by little into a recreation of an ancient temple with distinctly Mesoamerican vibes — and taking Data along with it.

At first, the effects on both the ship and on Data are minor. Strange artifacts are cropping up all over the ship, while Data kicks up his clay skills a notch by sculpting a mask that just happened to pop into his positronic brain. But while Geordi is scanning his android pal to check for any comet effects, Data asks what it feels like to lose his mind. Within a matter of seconds, Data declares he is different as a strange symbol appears on his forehead. And with that, his body is taken over by multiple personalities playing out a ritual revolving around the ancient civilization’s gods as the ship around him transforms into an ancient temple. From that point forward, the rest of the episode is just Data throwing out one hammy impersonation after another, like a theater kid performing his own one-man play.

As far as we know, Data couldn’t help any of this. But intent versus impact — and there’s no denying Data’s theatrics had an impact. And someone should tell him cultural appropriation is no laughing matter, especially if you look really goofy in that mask.

Aside from Reginald Barclay (Dwight Schultz) and Geordi La Forge, just about everyone aboard the Enterprise-D was getting some action — especially the android. But most Starfleet officers usually have the good judgment to avoid dating their coworkers. Take Commander Will Riker (Jonathan Frakes), who avoids dating his imzadi and future wife Deanna Troi (Marina Sirtis) for years to avoid fraternization problems, instead preferring to hook up with every new alien species that crosses his path. While Starfleet only forbids dating within a direct chain of command, it’s just messy business to date colleagues in any military operation.

But Data doesn’t really concern himself with professional romantic boundaries, hooking up not once, but twice with his colleagues. Technically, Data’s messy fling with Tasha Yar (Denise Crosby) begins with a drunken hookup. But after her controversial death, it’s heavily implied that things continued well into sober territory despite Yar being a senior officer to Data at the time. Even if there’s no legal impropriety on her part, it certainly represents questionable judgment from both parties. And Data is not just any typical Starfleet officer — he’s a literal android who would absolutely know their relationship would certainly have fallen into an ethical gray area.

He repeats the pattern again in “In Theory” with Jenna D’Sora (Michele Scarabelli), a lieutenant junior grade security systems specialist. Once again, neither is under the other’s direct command, so it’s technically legal — but you just know it made ship-wide staff meetings with both officers in attendance pretty awkward after their breakup. And positronic or not, there’s no way that man doesn’t have information on rebounds in his database.

As uncomfortable (and unsexy) as it was to hear Data talking about being “fully functional” to a grinning Yar, it’s far worse to see him getting all hot and bothered by the Borg Queen (Alice Krige) in “Star Trek: First Contact.” And according to longtime “Trek” director Jonathan Frakes, Data and the Borg Queen most certainly did the deed.

The whole filthy business takes place in the latter half of the movie, after Data finds himself kidnapped by the very saucy Borg Queen. In her efforts to crack his encryption and get her sleazy little paws on the Enterprise-E, she’s willing to try just about anything. Tapping into Data’s burning desire to feel human, the Borg Queen activates his emotion chip and grafts a patch of skin to his endoskeleton, the ultimate android foreplay. When she directly asks about his sexual capabilities, Data gives what we can only assume is his favorite pickup line, telling her he is “programmed in a variety of techniques.”

Now, we know the emotion chip — not to mention the stress of being kidnapped by a hot, scary babe — had our little Pinocchio turned upside down and every which way. But the mask defense can’t help him here, especially since we learn the whole act was just a ruse when he turns on her. It sure seems like he could have turned on her sooner but made sure to get some action in first.

By far one of the most irresponsible things Data does is habitually conduct experiments on his own brain, which can (and do) lead to chaos and potential danger for his fellow crewmen. Data used company time to alter his own consciousness on multiple occasions throughout “Star Trek: The Next Generation.”

Some of these experiments are merely concerning, like when Data transfers his child’s memories into his own positronic brain after she fails to thrive in “The Offspring” or when he accidentally turns the holodeck into a Data-themed “Being John Malkovich” in “A Fistful of Datas.” But occasionally, his experiments are downright reckless, like when he intentionally chose to keep his dream program running in “Phantasms” despite full awareness that he’s having some dark nightmares. Deanna Troi would later regret encouraging this reckless decision when it caused him to stab her while sleepwalking.

The worst experiment by far was Data’s emotion chip. Despite knowing just how dangerous this chip could be from his past issues with Lore (also played by Brent Spiner), Data chooses to reinstall the darned thing in “Star Trek Generations.” This leads to a string of unprofessional, obnoxious, and unhinged behaviors, not the least of which is his singing about little life forms while scanning a planet.

For a guy who is seemingly governed by data and information rather than emotions, Data sure is prone to emotional outbursts — even if sometimes they’re warranted. Still, you can’t go around shooting people no matter how much they might benefit from a run-in with the agonizer. But once again, that’s exactly what Data did when an absolute space tool kidnapped him to place in his collection of intergalactic toys in “The Most Toys.”

After Data’s shuttle presumably explodes, his crew thinks that he died. That’s convenient for the guy who staged it, an entitled Zibalian collector named Kivas Fajo (Saul Rubinek). Fajo then forces Data to sit in a chair without moving, killing his own assistant Varria (Jane Daly) and telling Data he’ll continue to kill others until the android complies. In the ensuing melee, Data gets a hold of the disruptor, aiming it at Fajo. At that precise moment, the Enterprise arrives to beam him up. Back on board his own ship, Data catches side-eye from Chief O’Brien (Colm Meaney), who reveals Data’s disruptor — set to kill — appeared to have accidentally discharged during transport before O’Brien managed to deactivate it. “Perhaps something occurred during transport,” Data replied.

As a Starfleet officer, Data would certainly have the legal and ethical standing to kill someone in self-defense. But at the moment the disruptor discharges, Fajo is unarmed. Even more alarming is Data’s reaction to O’Brien’s revelation. Without hesitation, Data blatantly gaslights O’Brien with his feigned ignorance despite knowing he’d meant to kill Fajo. This tells us two things: First, that Data would absolutely break his programming to kill someone and second, that he’s just as capable of lying as his brother, Lore. Now that’s positronically ruthless.