This episode was directed by Rider Strong, who played Shawn Hunter on both this series and Boy Meets World (1993).
When Riley asks Topanga about her first date, Topanga answers, then changes it a lot. This is a nod to "Boy Meets World," where there are many different stories on how Topanga and Cory met.
The events of this episode mirror the third season premiere of Boy Met World episode "My Best Friend's Girl" (1995) when Shawn asked Topanga on a date to spur Cory into admitting his feelings for her.
Rowan was nervous about having her character Riley date Peyton Meyer's character Lucas because of the large age gap between Rowan and Peyton.