I've read a sci-fi novella with this very premise. Indian guy uses an AI guide designed by his roommate to pick up (sparse, almost non-existent) indian girls. He catches one with a cheesy pickup line to do with a TV show, but it turns out the girl's AI was the one interested, and not the girl herself.

In the end, the AI bots fall in love, but the guy is crushed when he finds out the girl just wants to play the field a little (girls are rare in this setting). Frustrated with his efforts, the guy decides to go out dancing with his roomate, who liked him more than a friend all along