The key to answering this question lies in what type of entertainment you're looking for...

If it's a nice dinner I'd head down to Ruston Way or try the Melting Pot or El Gaucho on Pacific although both can get pricey. Ruston Way is a better option if you don't want to drop $$$. There is an Anthony's at Point Defiance, but it is a little more causal than most of their other locations, although the menu is about the same. There is an Anthony's Homeport in GH as well.

Also I'd recommend getting a reservation anywhere you go. It's homecoming season and all of the options above are popular choices with that crowd. I got a growler filled last Saturday night at the RAM and the whole area was packed.

I second the Parkway Tavern. I'm not much of a beer person, but it does have a great atmosphere. Same goes for the Tides in GH and the SPAR in Old Town. Pomodoro in Proctor District in quaint and great for Italian.

Chopstix is another place I'd suggest having a reservation. It can get very busy and in all honesty, it's more of a place for your wife to go with her girlfriends. So unless she's got her heart set on a piano bar, I'd go elsewhere. On the upside it is right across the street from a couple other bars (Jazzbones, E-9, Masa) so if you got bored there are other options. Varsity Grill also has a piano bar, but their food leaves something to be desired.

If you're into live music/nightlife, The Swiss is usually a good time, but it can get pretty packed depending on the band. Jazzbones, mentioned above, is also pretty good in this category.

I hope that helps.