This is Ring of the Ruby Dragon (1983), the first in TSR’s HeartQuest series of pick-your-path gamebooks.

I hadn’t ever heard of these until a couple years ago, and I only snagged a handful recently. As you might have already guessed, the series is romance focused and aimed at women readers. The cover’s trade dress and the die-cut window for the cover art is more in line with regular romance novels of the period than any D&D product. As far as I know, this is the only time TSR used a die-cut window, which is a good thing, because the cover stock is lighter than what you’d usually find on a cover like this. It makes the book real hard to hold when reading and the holes are real prone to tearing.

1983 was a moment in time when TSR was aggressively courting new customers. The cartoon, toys and Endless Quest books aimed to net kids and HeartQuest was an attempt, no matter how brief, to appeal to women. I expected these to be straight romances, but was pleasantly surprised that the interior illustrations (by a very rushed or unenthusiastic Jim Holloway in this one) featured actual D&D monsters. That gave me hope that these were actually going to be good, a mix of adventure and romance that might have in some way anticipated the combination of the two in videogames like the Dragon Age series, or even Baldur’s Gate (<3 the good widow Jaheira). But no, they’re pretty bad.

This one puts you in the shoes of a jeweler’s daughter whose father has been kidnapped. She falls in with two knights (both of which are potential romances) and a lady thief (who can also end up with one of the knights) and together, you pursue the dragon kidnapper. Cool thing: the dragon has charmed lots of woodland creatures who wouldn’t normally be adversaries in a D&D game. Uncool thing: the protagonist cries a lot and despite being able to cast spells via her magical jewels, the other characters handle most of the action. The Larry Elmore cover painting is cool at least.