Depends on what you like to do. There are a lot of good restaurants on that side of town off of Sandlake.
Moonfish Grill, great place for Steak and Seafood
Timpano's
Roys
Seasons 52
Samba Room's not bad.
I can't speak too much for the night life during the week but you are not too far from Millenium Mall, which has Blue Martini, high end club with mixed clientel. Young to old...not so rich to rich...
http://www.bluemartinilounge.com/eventsorlando.html
Not sure what their busy nights are. Mondays used to be and I am sure they are busy on the weekends.
Cafe Tu Tu Tango is a pretty cool restaurant on I-drive that I like, think of it more of a date place but it's something different with appetizer sized portions that you share.
http://www.cafetututango.com/
Opa is down there in Point Orlando, can be fun, (Encourage people to eat on the tables) but usually not busy during the week. Maybe that's different now since it's tourist season.
http://www.opaorlando.com/home.php
Downtown Orlando for Wednesday, Urban Flats has a Wine down Wednesday event, pay $18 unlimited wine and food buffet til 7 or 8 can't remember. Pretty strong following especially if the weather is nice.
You could catch a Magic Game, they are playing tonight, not sure how available tickets are. Heard the new Arena is very nice.
http://www.nba.com/magic/schedule/
HTH, if you are looking for other suggestions let me know.