The 49-year-old actor tried his hand at dating Sophia the robot in a video posted to his YouTube channel on Thursday, and it didn't exactly go well.
While the humanoid robot developed by Hanson Robotics is able to display more than 60 facial expressions and has participated in many high-profile interviews, she didn't seem to be a big fan of Smith's.
"Thank you for coming. This is beautiful. I wanted to meet you for a really, really long time, and being here with you in the Cayman Islands, I've got to say, I'm feeling a little something," Smith tells Sophia in the video, handing her a glass of white wine, which she didn't pick up.
"I've heard your songs. Not for me," Sophia tells Smith. "They show us I, Robot just to make sure we truly don't get any ideas."
Watch the awkward date -- including Smith's attempted kiss -- below:
"I just met Sophia the Robot. She wasn’t feelin’ me," Smith added on Instagram. "I guess based on my History with Robots."
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"Love is Like Gardening... I have learned to focus on HELPING you to BLOSSOM into what YOU want to be (into what you were born to be)... Rather than Demanding that you become what my Fragile Ego needs you to be."
"I’ve learned to take pleasure in Nourishing YOUR dreams... Rather than wrestling with you to Fulfill my Selfish Needs & Satiate My Insecurities," he continued. "I have learned that Love is Listening. Love is Giving. Love is Freedom."