I think I went to Last Grenadier with Aeryk one time.

Games (besides Upwords etc.) that we've gotten a lot of mileage out of:
- Cargo Noir
- Small World
- Carcassonne
- Agricola (which surprises me a bit, since it's a bit on the complicated side, but the theme is so good and well-tied into the mechanics that it's surprisingly appealing for non-gamers)
- San Juan
- Dominion
- Zooloretto
- Roll Through the Ages (saw your "bonus content" draft)
- Balloon Cup

I think I could swing a Wednesday Fiasco.

[Update] Games that went over like a lead balloon:
- Pandemic (actually, she liked the game and we played it a few times, but the theme started making her so nervous that she doesn't want to play it anymore)
- Elder SIgn
- Talisman
- Battlelore