I had 2 very basic ideas for a Valentine's quest, which I will write for your consideration.
1 - Cupid tells you that it's Valentine, but there are three ladies all alone on the special occasion. For this quest, you would have to go buy Roses from Blossom, and go hunting the eligible bachelorettes of TMW NPCs

. My nominations for this are Wyara, Elanore, and Wendy (marriage NPC). Upon brightening their day, see Cupid for a heart-shaped reward!
2 - A quest to get each other matching anniversary rings. Done with two people obviously, this one involves each player doing something 'Valentine'-y to earn an anniversary ring. The quest is finished by both players seeing Cupid with the rings equipped. Feel free to elaborate if this sounds at all good

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Tiana wrote: I apologize if I gave anyone the impression that BC is the troll-king of the GM's. That title is rightfully held by mrgrey

<Mistakes> you are too difficult to troll
<Frost> Germans have Chess Boxing. English have Cheese Racing.
<Frost> I'm slightly terrified what the Russians consider violent sport.
<o11c> chatroulette
<Jaxad0127> YOu can't grab yourself.
<Jaxad0127> Elenore explicitly prevents it.
<Mistakes> speak for yourself