IMHO best steak in Baltimore is the Prime Rib on Calvert St in Mt Vernon. It's about a $5 cab ride from the Inner Harbor, but if you drive they have free valet parking. Requires a jacket and tie. Around the Inner Harbor there the the expected chain steakhouses.Ruth Chris, Shula's, Mortons, and Capitol Grille.
When I think fun night I think tapas at Pazo on Aliceanna in the Fells Point area. Also just a short cab ride from the Inner Harbor (and free valet).