Strife and Lilith

• First Meeting: It is unknown when Lilith and Strife first met, or if they ever even became aware of each other's existence. The only episodes that both characters appear in is "1.07 - Inn Trouble" - where Lilith is only seen dancing with the band, while Strife spends most of the episode invisible to mortals and plotting with Discord, and "1.11 - Battle Lines I"/"1.12 - Battle Lines II" - where Lilith is kidnapped by either Strife or Discord, while Strife spends most of the episode in the guise of Fake Cavil.
• Relationship potential: Comic relief and/or an accident with love potion.

Is there any basis in canon?

• Not so much in canon (see above explanation of how rarely their paths crossed), but there was definitely chemistry between the actors at some point. Jodie Rimmer stated in an interview that she dated Joel Tobeck when she was 21 (which would have been a few years before Young Hercules filmed).

Fanfiction featuring Strife/Lilith

• Why Do Fools by Achaea - Strife falls for Lilith after an accident with Aphrodite's love potion.