Dragon's Dogma

When you babysit that one rich girl in the main town/hub, do everything she tells you and fast, but make you don't get too far from her. Also, by the end of the quest, let her win the foot race as she'll give you a gold statue that I'm pretty sure you can't get anywhere else in the game and you can use said statue to give to a merchant so that they'll like you more and stock up on better equipment to sell. I had to make due with a silver statue for that mistake.

While I'm on the topic of this family, be sure to help out her father (Fournival) when his side quest comes around, his shop sells some really useful items such as God's Finger, which can kill just about anything in one hit. Though, you can only carry one at a time. I'd recommend it for bosses. Namely the Cockatrice.

Also, make sure your party is balanced out as it pays to be prepared for any encounter. Having a healer around is always a good idea in most games, and while mages and sorcerers require a bit of babysitting, they are actually quite useful in terms of support. I've actually had to rely on the team's Mage to be the damage dealer in my first fight with a dragon, as I had really shit equipment at that time and couldn't do piss for damage against it, even with heart shots (playing as a strider/assassin).

Finally, make sure you finish up as many side quests as possible before proceeding with the story. Similar to perma-failing quests, a lot of side quests will be canceled and impossible to finish if you blow through the story too quickly, causing you to miss out on some pretty worthwhile quest rewards.

where the dragon is supposed to take my love interest.

I hate to sound vague, but if I remember correctly, the girl is taken to a citadel. It should be up North West at a Gran Soren campsite. The best way I can describe the area is;
Lots of Goblins, and Harpies, occasional Chimera, and at night there might even be vengeful spirits and a Wight. There's many black tar swamps, and the area is very rugged and there's a cave that's VERY big in the vicinity.

The cave is best described as many broken bridges and many detours along the way, probably 4 levels. Monsters inside consist of Cyclops, Vengeful spirits, Sulfur Saurians, spiders, Harpies, Goblins, and if you've proceeded far enough in the storyline, a Cockatrice.

But yeah, she should be here. If I had the map up right now I'd tell you the exact location but I recently started playing Hard Mode again.