Ooh that's a tough one, Tyler hasn't had a Valentine's in a while but he does get some occasionally as a Senior.
The best he's probably gotten were some "obligatory" chocolates from Clair one time in a hangout session. Clair handmade it herself, so he cherished every bite

The Worst was probably being gifted some Flowers, which happened to be a bunch of Floette... That's how Tyler got chased by an Angry Florges the whole school day--