Dating in Chicago, IL ♥ Singles and Dating

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Category: United States / Illinois / Chicago


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Dating Tips and Advice for Singles in Chicago, IL

"Unless you have known the person you are going on a date with for a while, always meet at a public place, dinner or coffee/soda's are a great first date. That way you can talk and get to know each other in a safe environment. And never go out for alcholic drinks on a first date, that can leave a bad impression. :)" -Hollie Sadoff, Streamwood

"A lot of girls that I have met always think that sense of humor is really important. Along with that is honesty, kindness, and outgoing. Stay away from the ones who ask what kind of car you drive, your clothing brand, and your bank account. I like taking my girl to the Gale street inn, or any really nice restaurant. I love going to all of the festivals and everyone I go with always has a good time. It's nice to meet girls at a bar, but if you can meet a girl at church who looks good, then she is probably a keeper. " -Matt, Norwood Park

"Nice, comfortable places to go: Margies Candies, Sweet Mandy B's, Nature Museum

It's better to say "So What" than "What if?" Translation: It's better to try and fail, than to not try and wonder if you would've failed or succeeded." -Adrian Castillo, Little Village

"Chicago in the summer is can meet people all over the place...especially downtown at a number of the events...Taste of Chicago, Jazz Fest, Blues Fest, film festivals, etc, etc. Culturally, it's on point." -A.D., south suburbs

"There is loads to do in the Chicagoland area especially if you are on a budget. I am in college and cannot afford extravagant things to do. I've found ways around that. Museums have weekdays where they are free admission. The White Sox have 1/2 price game days. Navy Pier has free fireworks on Wednesday and Saturday nights throughout the summmer. Things like that provide great places to take dates, on a budget." -Anonymous,

"If a man wants to wow a woman, take her on the Odyssy. It's a dinner boat cruise that leaves from Navy Pier. You get dinner/dancing and a very romantic night on the lake. It's also fun to dress up sometimes!" -Connie, Near West Side

"My advice for all singles in Chicago is to be yourself. Whatever that means. I go to bars and clubs, and just constantly see "that guy" who wears expensive clothing and accesories trying to impress women. Are there any women out there still looking for something real? Something a good laugh." -Gil Lazaro, Skokie, Il

"Be confident... If you see someone you're interested in, go talk to them! This may be your only chance... it's a big city!

There are so many things to do in the city. Be more original... think beyond the traditional dinner and a movie. Go on a bike tour, go for a walk by the lake, go to a jazz club..." -Devon, Lakeview

"There are so many things to do in Chicago, just take your pick. In the winter, a nice dinner at a cosy restaurant would be nice. In the summer, a walk along Lake Michigan is beautiful. The city is big and with many wonderful people. Honesty is the best policy, along with a sense of humor and compassion." -Nicki, Chicago/Northwest side/Edison Park

"My fave cheap, low-pressure first-date place is Margie's ice cream on Western. You can split a HUGE, incredibly fattening sundae for about $6. And if that goes well, there are a number of bars and coffee shops close by where you can continue the conversation." -Anonymous,

"Stay away from downtown Naperville bars and hang-outs. The place is over-run with stuck up college kids and trendy wannabes." -kris, Downers Grove

"Chicago is a great city for the plain fact that on any given day there are numerous things to do that either cost little money or none at all. Be adventurous. Learn to free yourself and try new things with an open mind. Maybe the free japanese dance lesson at the center seems boring but could be really fun (or funny) if you and your date are open enough to know its cool to laugh at each other (as long as its not demeaning). Just be up for anything and have fun. Be creative. It's the best city to allow you to do so!" -Charlotte, Lincoln Park/Depaul area

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