Name: Geoff Ruttenberg

Age: 42

Hometown: Chicago, IL

Occupation: Real Estate Developer

Status: Badboy

Diva Minds Want to Know…

1. Where do you like to flirt?

Really, I see no reason to limit flirting to a specific time or place. When the mood is right…or the connection is apparent…it’s time.

2. Where is your favorite table for two?

Chicago is known for its great food and the city offers plenty of variety to satisfy nearly every taste. While tourist-favorites Lou Malnati’s and Gibson’s Steakhouse won’t disappoint, locals will tell you that some of the best city restaurants are found off the beaten path. For a unique pizza experience, I recommend the Chicago Pizza and Oven Grinder Co., situated directly across from the site of Al Capone’s St. Valentine’s Day Massacre. Sapori Trattoria, located in Lincoln Park, is a little-known restaurant that offers one of the best Italian menus in the city. For visitors looking to star gaze while they dine, Japonais, Le Passage, and Spiaggia are some of the favorite dinning spots for visiting musicians, actors and athletes. Likewise, Underground and the Crimson Lounge attract their fair share of local and national celebrities, too. I recommend browsing Yelp or Chicago Metromix for more suggestions, as these websites provide candid reviews on most any restaurant and bar in the city and can be really helpful if you are looking to travel to locations outside of the immediate downtown area.

3. Where should we stay when we visit?

Many tourists will feel most comfortable staying at a hotel that is within walking distance of Michigan Avenue, the Downtown area and Millenium Park. From any of these spots, finding your way to other parts of the city via public transportation or a taxi will be relatively easy. With that said, there are many places to choose from based on what you are looking for, who you are traveling with and your hotel budget. I recommend using a travel site like Orbitz or Travelocity to find the best deal for your dollar, however some of my favorite downtown hotels include The Drake Hotel located on The Magnificent Mile in the Gold Coast, the W on Lake Shore Drive, The Peninsula Hotel, The Hotel Sax (the old House of Blues Hotel) known for its trendy décor and hi-tech amenities and for families, Hotel Monaco, a pet-friendly boutique hotel that offers a complimentary wine hour for adults and goldfish in each room, sure to excite both kids and couples alike and another newer boutique, the Dana Hotel, in the trendy River West area.

4. What qualities do you find irresistible in a woman?

Personality and sense of adventure is a must. I am looking for someone that is enthusiastic about life and searches for humor and adventure in every experience; there is nothing I find more attractive than a woman who loves to laugh.

5. Where can we find you on a free Sunday afternoon?

That depends on the season and which sports team is playing that day. Nothing is more enjoyable than relaxing at Wrigley Field while the Cubs play, or tailgating before a Bears game. Occasionally, I like to treat myself to Sunday brunch at the Four Seasons hotel.

6. What do you love most about your hometown (besides our arrival)?

Chicago is a great four-seasons town. There is nothing more charming than wintertime in the city, as the downtown-area sparkles underneath strands of lights and freshly-fallen snow. In spring and summer, the city feels renewed as people begin to spend most all their time outdoors, traveling to Oak Street Beach on Lake Michigan, enjoying the parks and dining outdoors on rooftops and patios. Autumn provides the perfect setting for outdoor family trips, as people get outside to BBQ, visit Lincoln Park Zoo and walk along the lake one last time before the first snow falls.

7. What should we bring when we visit? What should we leave with?

Be sure to come to Chicago with an open mind and sense of adventure. The Windy City offers plenty to do for the average visitor, from theater and museums, to sports and dining. However, the pulse of Chicago lies in the neighborhood attractions scattered throughout the city. Websites like and Metromix provide a daily overview of what’s going on throughout the town, including neighborhood festivals and block parties, as well as the annual events that make the city unique. Chicagoans love to talk about their city and give advice to tourists, so don’t hesitate to approach a local to get an inside tip during your stay. Those who take a chance are sure to leave with a positive experience of their stay and some great stories.

8. What do we absolutely have to see while we’re there?

Chicago is a large city made up of many small neighborhoods; each offering a unique flavor that’s all its own. Beyond the tourist-friendly downtown area, which houses Millenium Park, The Sears Tower and The Magnificent Mile, there is plenty to do and see. Some of my favorite areas include Lincoln Park, known for its small individually-owned boutiques and restaurants, the Gold Coast, home to some of the most exclusive and high-end stores in the city and the up-and-coming West Loop area, where Restaurant Row and Oprah’s studios are located. If you’re lucky enough to be in Chicago during a cubs game, I recommend taking the trip up north to Wrigleyville right off the Addison Red Line stop to visit the stadium, walk along Clark Street and if you’re lucky, even score tickets to the game.

9. Any areas of town we should avoid?

Like any big city, Chicago has its share of locals that are not ideal for tourists. However, most natives are very friendly and willing to provide directions or lend a hand to those who may appear lost. With that said, talk to your hotel concierge, approach a sales clerk or talk to a waiter, and you’re sure to stay on track!

10. Any local secrets you want to share?

Chicago is a very maneuverable city, offering a variety public transportation options that are relatively simple to figure out. The “L” (Chicago’s elevated subway system) provides a simple and inexpensive way to travel to some of the city’s most popular spots. Or, check out one of the free trolley rides that run regularly throughout the year to a number of tourist-friendly locals, including Navy Pier, the Lincoln Park Zoo, Michigan Ave. and more. For tourists wanting a behind-the-scenes look at the city, the Walk Chicago Tours, led by local residents eager to share their passion for Chicago, are a great way to get an insider’s look at the town while also avoiding the large group and bus tours that populate the city. Covering topics from art and architecture to neighborhood hidden gems and Chicago’s gangster past, these tours are budget friendly ($30 or less) and cater to small groups of people to provide a custom view of the city. Reservations are required, so they recommend you call in advance.