Kids with a sitter | See Jane Fly

The Penthouse

1111 Second Street, Santa Monica; 310-393-8080; www.thehuntleyhotel.com/penthouse-restaurant.php

Put on that sexy black dress, and hit the number 18 on the elevator at the Huntley hotel. Newly renovated, The Penthouse boasts 360-degree views of the ocean, mountains and twinkling City of Angels. Slink up to the horseshoe silver bar for a blackberry-pineapple sidecar, then dine in the sky as the sun sets into the Pacific. An after-dinner drink in the lounge wraps up a perfect romantic evening.

Pacific Resident Theatre

707 Venice Blvd., Venice; 310-822-8392; www.pacificresidenttheatre.com

The Westside’s most prestigious theater, this co-op has been around for over 20 years and has garnered numerous awards. With three separate stages, there are multiple productions to choose from and a wealth of talent to watch, so call to see what’s playing while in town. Head to Abbot Kinney for dinner before the show at AK, Gjelina’s or Joe’s, or have a drink at The Other Room after the show.

Hollywood Bowl

2301 North Highland Blvd., Los Angeles; 323-850-2000; www.hollywoodbowl.com

This famous architecturally significant outdoor amphitheater is a jewel with state-of-the-art sound. Picnic in the boxes on delectable food by Patina while enjoying rock ’n’ roll, jazz, the symphony, world beat and more. The Bowl is a glorious way to spend a romantic evening under the stars and a prime spot for people watching and a magical evening in LA.

Old Globe Theater

Uptown - Balboa Park | 1363 Old Globe Way, San Diego; 619-231-1941; www.oldglobe.org/

If you’re visiting San Diego during the summer, take in Shakespeare under the stars (and under a blanket on chilly evenings). Not the summer? This Tony Award-winning regional theater still make for a great night out, especially with bigger-budget shows in the main theater (which are often Broadway bound) and more intimate—sometimes quirkier—shows at the theater-in-the-round.

Anthology

Downtown - Little Italy | 1337 India Street, San Diego; 619-595-0300; www.anthologysd.com

Modeled after the great supper clubs of the 30s and 40s, this sleek entertainment venue has all the ingredients for a sexy night out: delicious cocktails, excellent New American cuisine and live music. Musical acts are eclectic and might include jazz, classic rock, blues, Latin or world music. Want to skip dinner? Grab a drink and appetizers at the bar or head upstairs.

Sogno Divino

Downtown - LIttle Italy | 1337 India Street, San Diego; 619-595-0300; www.sogno-divino.com

Not sure what you’re in the mood for? At this charming Little Italy wine bar, you’ll be spoiled for choice. With an extensive wine menu from around the world—which you can enjoy in any size from 1-oz. pours on up—and a seductive array of hearty appetizers, you can’t fail to find something to your liking.

Avec

615 West Randolph Street, Chicago; 312-377-2002; www.avecrestaurant.com

This petite, boisterous lounge that resembles the wood-lined interior of a wine cask or a Swedish sauna offers a simple European-inspired incarnation of a wine bar. Rub elbows with locals while feasting on flatbreads, salumi and cheeses accompanied by a mind-boggling list of wines from around the world.

Alinea

1723 North Halsted Street, Chicago; 312-867-0110; www.alinearestaurant.com

Alinea is like a Willy Wonka factory for grown ups. Chef Grant Achatz is a pioneer in the field of molecular gastronomy, so you can expect an unforgettable meal whether you choose the 13-course tasting menu or the 23-course tour. The dining room itself is a study in streamlined modernism with some whimsical pops of color, perfect for a memorable night out.

Graham Elliot

217 West Huron Street, Chicago; 312-624-9975; www.grahamelliot.com

Chef-owner Graham Elliot Bowles takes a decidedly rock 'n' roll approach to his cuisine (in fact, the toque is also a musician), adding offbeat touches like lavender marshmallows, parsley bubbles and vanilla ice (get it?) to his delightful dishes. The dining room is a study in hipster chic: picture exposed brick, a copper-clad communal table and a rock soundtrack that skews favorably toward the '80s.

Japonais

600 West Chicago Avenue, Chicago; 312-822-9600; www.japonaischicago.com

Spend a decidedly adult evening stylishly sipping and socializing at Japonais, the sexy Japanese restaurant and lounge located along the Chicago River. Splurge on signature dishes like Kobe beef prime rib and maple leaf–smoked duck, paired with Floating Orchid cocktails if you're really feeling saucy.