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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

For close to 100 years, people have gone to the movies with romance in mind (the darkness, the entertainment, the talking points for afterward).

Although this prototypical date is time-honored, never-fail and always wonderful, here are two modern updates you can try this week:

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

There is something about a breathtaking view of a city skyline that screams romance.

The Eiffel Tower in Paris and The Empire State Building in New York City have always been linked to such glory and spectacle, but let's not forget the iconic choices here in Chicago.

RICH MAN: A day at the Willis (Sears) Tower is a sure-to-be-fantastic and refreshing "Tourist in your Own City" date that 1.3 million other people visit each year.

The Skydeck and view is obviously very cool, but don't forget the exhibits about our great city, high-tech telescopes, and summer concert series on the plaza – head over this Friday from noon-1:30 p.m. for music and dance by The Boilermaker Jazz Band.

Thirty bucks gets you in the express line to the tallest(?) building in the Western Hemisphere. It also provides you the opportunity to brag about the time you saw Illinois, Michigan, Indiana and Wisconsin from one spot. Cool.

POOR MAN: Enjoy a possibly even better view at the other tall dark building that is part of our pretty skyline known as the John Hancock building.

For the cost of a drink as little as $7.50 (non alcoholic) or a $12 cocktail, you can head up to The Signature Lounge on the 96th floor without an admission fee. You¹ll get great views of the beachfront, Lake Michigan, and the city and, most importantly, a tasty beverage.

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

Here at Single City, we really care about the friendships that keep you sane.

So when you’re sick of trolling Match.com or your local pub for a date this weekend, consider redirecting your attention to build the platonic portion of your social calendar.

Try, for instances, MeetJoe.net, a kind of friend match-maker service.

Started by “Joe” of Roscoe Village, the service promises you one meeting with a single person or in a small group setting after a personal consultation with Joe himself, for the initial ticket price of $29 and then $29 per friendly set up thereafter.

Joe also calls ya the next day to see how the friend-date went, making the service what he calls, “the most low-risk, high-reward social opportunities” you’ll find. Citing customization, privacy, quality, service and value, Joe also describes himself to be a “personal social concierge.”

Maybe you’re current bestie is getting married and you need a new single girl in your life to go out on the town with. Maybe you’re new to the city and just want someone to eat dinner with. Maybe you’re just bored! Whatever the reason, if you are 21 and in the area, Joe wants to set you up with the friend of your dreams.

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

Locals often lament Chicago's winter cold is utterly bone-chilling, but “the summers make up for it.”

And while the list of things to love about and in a warm Second City is endless, a visit to the beautiful Museum of Contemporary Art is a must – if only for their beautiful outdoor space on Tuesday evenings (5:30-8 p.m.) through Sept. 28.

RICH MAN: Entry to “Tuesdays on the Terrace”
hosted by our impressive neighborhood art museum – one of the world’s largest for contemporary art – is just $22 a person. It is a steal considering you are treated to a jazz concert as you enjoy an internationally themed dinner buffet prepared by Wolfgang Puck catering, which uses locally-grown produce from the MCA’s own farmer’s market.

RSVP immediately for Tuesday’s night of fun featuring Brazilian cuisine, including grilled churrasco, chimichurri swordfish, grilled eggplant, rice and tomato salad, farmers market salad and dessert.

POOR MAN: So Wolfgang’s out of your league? That’s OK, because you can still enjoy the same jazz concert on a great summer night at MCA with the cuisine of ... a county fair (still romantic!). Bring a blanket and find a spot on the garden lawn, where a few bucks will buy you something from the outdoor grill (burgers, dogs) or drinks at the cash bar on the lower terrace. And while you’re, you know, at a fantastic art museum, walk around the sculpture garden too – all of this for free!

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

Smoking, religion, parenting are all accepted, and obvious, deal breakers.

But if you are dating in the city, sometimes it's the quieter ones that hurt your budding romances first. In the spirit of finding the mildly bumpy but everlasting road to true love, keep these deal-breakers in mind for your next first date if you are hoping it will be the last.

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

The grand theater is not just for snooty winos and drama geeks and freaks. Often times, it is just exactly what it is --fun!

And it is a great date idea, although the key for it to work for the masses is to stick to something more low key and modern since the ballet or opera are two definitely acquired tastes. Chicago is full of these kind of gems, so here's two to consider this weekend:

RICH MAN: A good tried-and-true story is almost a guarantee for good theater. Currently playing at the Lookingglass Theater is Lookingglass Alice – a fantastic adaption of the Lewis Carroll original. The exterior looks like a castle, and the space is very small and cozy, which attendees unanimously agree there isn't a bad seat in the house. It is also centrally located next to the Water Tower Place, making for a prime opportunity to walk along the beautiful Mag Mile post or pre-date. Tickets are $32 to $64.

POOR MAN: Support your local artists by going to the Viaduct Theater to see their most current vision That Sordid Little Story – an eccentric bluegrass musical, half of which is in Spanish – by The New Colony about a prophetic concept album that takes its protagonist, Billy, on a journey through the Bible Belt. The music is enjoyable even if you aren’t a bluegrass fan in a must-see Chicago theater with a relaxed atmosphere.

The best part: There’s a bar inside so you can drink while you watch instead of just slamming and sneaking alcohol in during and from intermission. The show is funny and the show's eccentricity leads for great discussion later. $25 gets you a ticket in to the air-conditioned spectacle.

Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

There are many conquests on the average Single Life’s Bucket List – crazy sexual escapades, dates with a millionaire and the race to see how many people you can make out with on one backpacking trip through Europe, are common items.

But it is speed dating that is perhaps among the most synonymous for such a youthful list of reckless dating and mating. And like an elderly man who checks off sky diving, speed dating is an exciting unknown that you’ve probably “always wanted to try,” although the fear of throwing up in your mouth was also omnipresent.

On a warm June evening, I had 17 mini-blind dates in under two hours thanks to an event for college educated 20- and 30-somethings that was organized by Date and Dash (www.dateanddash.com).

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

There’s little explanation needed for why we all love fireworks. After all, that big, explosive, pretty, bright lights display is a cliche for chemistry for a reason. So as you plan dates for this weekend’s celebration of America’s independence, here’s hoping to seeing some fireworks in the night sky and feeling the fireworks all night long.

Sweet Talk in the City

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

Here is June's roundup of the 10 best, worst and most hilarious verbal exchanges I've been blessed to witness:

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

For two miles, one man after another -- six total -- stopped to help my friend Sam this weekend on the Lake Front path. Clad in a coral sundress, she was a damsel in distress when her blue Schwinn road bike’s crank fell apart and she was forced to walk the “piece of $^*&#” (her words) home.

One man, in his 40s, asked her three questions in this order: first, her name; second, if she could walk it home; third, if she was “married, single???”

Taken a-back by the straight-forwardness, immediately, I thought, biking must be sexy.

And if you, too, believe that to be a universal truth, try this week’s date ideas as soon as possible!

RICH MAN: Bicycling and charity work --makes ya look good, makes ya feel good. Have both at the Friends of the Parks’ L.A.T.E Ride on the overnight between July 10 and 11.

Register for $45 per person for this 25-mile benefit ride, where 9,000 cyclists will meet at the Buckingham Fountain at midnight Saturday-into-Sunday and bike through the skyscrapers downtown, the Lake Front by starlight, and many city neighborhoods to end with the sunrise over Lake Michigan and then an all-you-can-eat breakfast at Goose Island after (an additional $7).

All money benefits Friends of the Parks, a 34-year-old not-for-profit parks advocacy group. And I’m not gonna tell you this will be an easy ride, but event coordinators claim the the 25-miles will be all flat roads (except for bridges) and is “doable for cyclists of all levels.”

POOR MAN: Anyone who has not experienced Chicago Critical Mass must!

Thousands of bicyclist take over the streets for this free monthly bike ride across the city. There is a certain amount of rebellion (A big proverbial “Suck it!” to the motor vehicles in the Loop, some of who will honk in dismay) and a certain amount of care-free youthfulness to the event (lasts around three hours through the ups and downs of city neighborhoods). People yell “Happy Friday,” some dress up, some come shirtless, some bring boom-boxes and play Michael Jackson -- all of which will put a smile on the face of you and yours. Rain or shine on the last Friday of the month, meet them at 5:30 p.m. at Daley Plaza, Dearborn and Washington, this Friday!

Also, North Side Critical Mass (Young Lincoln Statue, 5959 N. Clark) meets every second Friday and Pilsen (Tenochtitlan Plaza, 18th and Loomis)and Wicker Park (Polish Triangle, Milwaukee and Division) meet every first Friday.

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

There are many occasions in a person’s life where being single can become a consuming matter of fact. Sometimes to the entire world (New Year’s Eve parties, a sibling’s wedding, Italian restaurants on Valentine’s Day), and sometimes just internally. As I celebrated the anniversary of my life last weekend (hooray), I found lessons for the occasion that falls somewhere in between.

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

My friend Sam once slow-danced at a park with a boy -- the music blaring from his purple hatchback -- following a sweet first date. She was instantly smitten. Who knew such a simple gesture could be so romantic? Despite the guy's less-than-heartfelt description of the moment (“You just put your hands around the girl and stand around”), I still commended him for the well-played move.

After all, dancing is a kind of unspoken vertical foreplay, one that goes beyond the awkward embraces of middle school dances and (hopefully) the grinding bar-scene variety of later years. Even if you cringe at the thought, I hope you’ll still consider taking your next date to the dance floor with this week’s outing ideas:

RICH MAN: The Fred Astaire Dance Studio is offering a two-session special for $25 for new students, which includes one private lesson and one group class or “practice party.” The 30-minute private lesson covers the basics of the foxtrot, rumba, waltz and hustle.

There are a million options in the city for couples and singles dance lessons, but let’s give some credit to this particular studio, which is owned by Jesse DeSoto, who was on Season 3 of "Dancing With the Stars." And if you don’t know Fred Astaire, you really just don’t know suave. The iconic singing/acting/dancing machine sang the original version of most romantic of all slow-dance songs, “The Way You Look Tonight.”

POOR MAN: The super-popular outdoor Chicago SummerDance is back starting Thursday! The 11-week festival -- which runs every Thursday, Friday and Saturday night from 6 to 9:30 p.m. and Sundays from 4 to 7 p.m. through August 29 -- starts with an introductory one-hour dance lesson by professional instructors followed by two hours of open dancing on a 4,600-square-foot dance floor in the Spirit of Music Garden in Grant Park.

Swing, waltz, salsa, cha-cha and more at the largest outdoor dance festival in the country for free! Those too “shy” can rest assured that the 100,000-plus people who participate each summer are probably not focused on you, but on the mixed-bag group of people who show up, the eccentric dance floor made from recycled plastic and planted around a pretty garden, and of course the awesome live music.

Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

Let it be known that I predicted Hawks in 6 from day one of the playoffs -- that said, tonight will be a major sports-fan heaven just about anywhere you go. Here are the best and worst pickup lines for this special occasion:

Best: "What do you say we drop the gloves and go at it?"

Worst: "Don't Toews me bro." (This will still get a good laugh.)

Good luck boys! Time to puck up Philly!

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

Once upon a time, a novel called The Notebook was made into a sappy yet sexy movie that left people romanticizing Alzheimer's disease and fantasizing about rowboat dates through nature. Here's how to make those dreams come true (minus the debilitating disease):

RICH MAN: Once a month, Chicago River Paddle offers a "dinner cruise" called the Moonlight Dinner Paddle. For $45 a person, you get to choose a boat and head out with your sweetheart in the early evening from the Chicago River on the Northwest Side, stopping for a riverside picnic dinner of Persian chicken skewers and grilled veggies from Noon-o-Kabab vegetarian options available, before paddling back by moonlight. The trip is around three hours long, departing at 6 p.m. Call (773) 704-2663 soon -- this month's trip is on Saturday! -- for reservations.

POOR MAN: In the perpetual search for free (or nearly free) things to do in Chicago that might remotely be romantic, I am constantly defaulting to Chicago Park District offerings. This week is no different, because beach season officially opened on May 28. While the Rich Man enjoys turtle sightings and the antique Addison Bridge, you and your cheap date can hit Kathy Osterman Beach (aka Hollywood Beach), a native dune habit and bird and butterfly sanctuary. No life preserver needed.

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Note: Neither of these people are likely to be found on CoffeeDate.com.


Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

Ever since I started writing a dating blog, friends and readers have sent a steady stream of story ideas my way. The most recent one was CoffeeDate.com, a website that promises easy, low-key meetups. Since it sounded up my alley, I attempted to test it out. (The key word here is attempted).

The member profile fields are mostly standard -- age, gender, looking for, height, build, smoker, five things you can't live without, about me...and APPEARANCE? I laugh to myself and look at the drop-down box. Apparently, I am to rate myself as either below average, average, attractive or very attractive. The site says the answer will not be listed once I upload a picture. Interesting.

Before I even filled out the profile, a 30-year-old man named Robert had "winked" at me (Red Flag 1). As an optimist, I reminded myself that every site has got the creepy guy that winks at everyone (Red Flag 2) and looked at his profile, which had no photo (Red Flag 3). I moved on. (Full disclosure: I'm proud to say I am a woman without a checklist. I am a woman looking for a real, sparkling connection -- something that seems awfully rare with every man I meet these days.)

As I browsed the site in hopes of a Coffee Date with a man between 25 and 30 who lived within 75 miles of my location, the website, disappointingly, reported just four options (one of which was Robert. Red Flag 4). Two had pictures. Neither of them were interesting.

I left my profile up for a week to see if that incident was just a fluke, but eventually just deleted my profile. Unfortunately, I just could not test out the service because of the lack of members.

I should have known the service was too good to be true when it said it was"100% free to use - all we ask in return is for to you visit advertised coffee venues whenever possible." The site's gotta make money somehow, but the blatant advertising just does not seem very romantic.

And actually...it's not, because if Match.com is the Starbucks of online dating, CoffeeDate.com is the run-down, mom-and-pop gas station that only sells Folgers in a paper cup. And if you're like me and looking for a man between 25 and 30 in Chicago, those paper cups are limited to less than a handful.

Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

The best thing about "Sex and the City" for the average single gal is knowing we'll still be having fun into our 40s -- cheers to that!

In honor of the "Sex and the City 2" movie releasing this weekend, here are my picks for the three best quotes from the show on being single (cue the Cosmos!):


  • "Being single used to mean that nobody wanted you. Now it means you're pretty sexy and you're taking your time deciding how you want your life to be and who you want to spend it with."
  • MIRANDA: "We were the only single people in there."
    CARRIE: "Miranda, we're the only single people anywhere."
  • "If you are single, after graduation, there isn't one occasion where people celebrate you...Hallmark doesn't make a "congratulations you didn't marry the wrong guy" card. And where's the flatware for going on vacation alone?...I'm thrilled to give you gifts to celebrate your life. I just think it stinks that single people are left out of it."

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

"Sex and the City 2" comes out this week! To honor such a wonderful holiday sure to be religiously celebrated by women everywhere, here are two dates meant for you and your best girlfriends.

RICH WOMAN: Enjoy one of several "Sex and the City 2" movie premier events throughout the city and suburbs. My top pick: the VIP movie party and screening hosted by Noir Woman Magazine on Thursday night. It includes a "Sexiest Shoe" contest, movie trivia, pink Cosmos, prizes and fun. The fun starts with a 7 p.m. reception followed by a 9 p.m. movie showing at the ICE Theater, 210 W. 87th. Tickets are $50 at the door or $35 in advance.

POOR WOMAN: Sure, there is some irony to catching a cheap matinee viewing of one of the most glamorous movies (the wardrobe budget was a reported $10 million) of the year, but times are tough and a movie under $10 sounds like a dream, right? Go to an early Saturday showing for the biggest bang for your buck. Cosmos not optional.

Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

Baseball games make for great dates. Depending on who's pitching, you get three to four hours of quality time -- including beers, snacks and plenty of people-watching. Plus with all the down time, you get a real chance to talk without missing any of the action. Now that I've convinced you, get some tickets and make sure to heed these three lessons I learned from a recent date at Wrigley Field:

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1) Pay for decent seats. They don't have to be steps away from home plate, but minimally should be on the first level outfield or right behind the plate on the second or third levels. This way, you can avoid much of the frat-tastic bunch known to frequent the area.

2) Go on a slow weeknight. The mood is way more low-key and chill than, say, during a weekend game where there will undoubtedly be violence and vomit. Plus you can afford the decent seats previously discussed.

3) Take in the ballpark and stay the whole game. Declare ahead of time you demand to stay for the whole game. Yes, it's a long time to be sitting, so be sure to take a walk around by the 4th or 5th inning. Buy a postcard at the gift shop or search for that elusive funnel cake -- the historic Wrigley Field is majestic for fans and non-fans alike.

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

Last week, I went home to Los Angeles where at least a few of my friends are in nearly decade-long relationships (one stemming from 8th grade!). Consequently, I began to wonder about fate, and whether there really is such a thing as "the one." Even Google couldn't answer that question, but it did tell me that the idea of "star-cross'd lovers" began with Shakespeare's Romeo and Juliet some 450 years ago. Feel free to use the couple as inspiration -- minus the whole killing yourself part, of course -- on one of these astrology-themed dates.

RICH MAN: This Thursday (and every third Thursday of the month!) is Adler After Dark, the Adler Planetarium's after-hours event. It's the only time you can look through the Doane Observatory telescope, the largest telescope in the Midwest available to the public -- not to mention a chance to enjoy cocktails and appetizers amid the museum's other great exhibits, plus live music from local bands Perseus Noble, Royce and Black Umbrella Brigade. This embarrassment of riches isn't actually that expensive; a full night of romance (6-10 p.m.) costs just $10 per person in advance, or $15 at the door.

POOR MAN: If you can't get inside the planetarium for the fun, try hanging out just outside of it, in the equally dreamy and underrated man-made peninsula of Northerly Island. It's the most serene 91 acres you'll find in the busy city. Try laying out at the 12th Street Beach -- a date so simple and perfect, you'd think it was written in the stars.

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Afternoon Tea at the Drake Hotel.(photo: chicagoceli via Flickr)

Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

Tea parties have taken on a new meaning, but once upon a time, it was a high-society affair meant to hold your stomach over until a later lavish dinner. Tea time is not sexy, per se, but it can be romantic for some and a sweet treat for all. Here's how to do it up like a real aristocrat -- or a lowly peasant.

RICH MAN: For this very Old World date, go to The Drake Hotel for Afternoon Tea. For $30 per person, you get sandwiches, pastries, fruit, bread and scones and your choice of super fancy tea in the beautifully elegant Tea Lobby. Go any day of the year between 1 and 5 p.m., with each tea time lasting an hour and a half. The "smart-casual" dress code gives you a good excuse to look extra sharp for your date and the harpist (yes, a harpist!) provides good background music. Non-tea drinkers will still be able to appreciate the atmosphere at the fanciest hotel in Chicago and the famed powder room, which was listed as finalist for America's Best Public Restroom Contest last year.

POOR MAN: Enjoy a different kind of caffeinated date this week at with a Starbucks Happy Hour. Through May 16, participating Starbucks are offering half-price Frappuccinos between 3 and 5 p.m. Note: I generally do not advise any first-date involving coupons, Groupons or 2-for-1's, but man what a deal!

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