Studly guys with no shirts. Summer dresses gripping tight bodies. Joggers in tank tops. Rollerbladers in skimpy shorts. Bikinis, bikinis, bikinis. Yup, summer is upon us. Every year, I hear the same comments from my friends in the summer, male and female.
"I am so excited that summer is finally here. I'm definitely gonna get a boyfriend this summer."
"Oh my God, there are so many hot women on the beach; I'm going to meet a bunch this year."
"With all the street festivals, I am going to be hooking up a lot this summer."
At the end of the summer, few have nothing but complaints about how they didn't meet anyone, didn't talk to any bikinis on the beach. (When a woman you haven't met is in a bikini, it is inappropriate to refer to her as a women; instead, it is proper to refer to her as a sexy article of clothing — "Check out the Bikini over there." It's the same as calling male federal agents "suits" — "Who's the Suit?")
photo by Ken Ilio
So what's the problem? With all the street fests, barbeques, drunken Cubs fans, hotties on the beach, volleyball leagues, beer gardens — oh, hell, the list is way too long — why is it still as hard to make a connection as it is in the winter, when many more people stay at home, behind closed doors? Why do most people spend more time watching all of the Chicago summer eye candy, instead of meeting it? Here are some of the best places to meet people in the Chicago summer and how to go about it.
Before you can begin to meet people at summer hotspots, you must know how to flirt. Flirting is key to successfully meeting people. Oftentimes flirting is defined as any verbal communication between the opposite sexes that occurs in social settings, such as a bar or street festival. Nope. Flirting is communication between people that includes sexual overtones, denoting possible interest beyond friendship or a casual acquaintance. Flirting can appear as unnecessary touching, verbal communication or even non-verbal communication such as smiling or winking. Women often flirt with a smile, a wink or by unnecessarily touching a guy, often in the act of asking a question. A woman might ask something simple like, "Are you having a good time?" while running her hand down a guy's arm and smiling. Men typically flirt verbally with comments that make small sexual suggestions.
Many guys struggle with flirting. This is an excerpt from my book God is a Woman: Dating Disasters that provides guys with a good tip for practicing their flirting:
Flirting is key to successful dating and picking up women. Some guys are naturals, some aren't. How can a guy who's not good at flirting get good?
I used to suck at flirting. Now, I like to spend almost the entire first date flirting. I find it leads to more second dates. In fact, the best two relationships I've had started with excessive flirting.
How did I get good? I watched other guys flirt. I said things that popped into my head that I thought were too risqué to say. I pushed the envelope. These are the ways to get good at flirting.
Guys can practice flirting with other guys. What?! Relax, pay attention. When I'm out with other guys, we rip on each other all the time; it's how guys bond. This ripping is not all that different from flirting. Consider a tennis match I recently played against a friend. He hit a ball into the net softly several times in a row. I ribbed him, "Hey, if you're gonna play like that, at least trade those shorts in for a skirt."
After he had a few miss hits — gifts to me on points he otherwise would have won — I ribbed him again, "Slut; I'll drop you off later on your corner."
One day I was playing hockey when the opposing team scored a soft goal through our goalie's legs. Our best defenseman turned to the goalie and said, "Close your legs, you whore."
This is not that different from the day I approached a woman who played on four different volleyball teams and asked, "You're just a volleyball slut, aren't you?"
Practice with the guys then tweak it a little for the ladies. Good flirting will be the result.
Now that we've covered flirting, we can move on to actual summer hotspots.
Barbeques are typically the first events of summer, occurring as soon as the weather turns nice. They are opportune times to meet people because they tend to be smaller, more intimate events of the season. There is not a lot of noise and the luxury of the simple icebreaker, "How do you know the host?" Look for a date, based on your conversation. (If you talked about cicadas at one point, for example, casually suggest a trip to a forest preserve.) Don't be specific about the actual day and time of the date; keep it loose and just use the suggested date to get or give digits (the phone number). You can reconnect when you talk on the phone. If the flirting and conversation are going really well, suggest going for a walk, perhaps to get some ice cream — or suggest heading to another place, such as a bar for a drink. Use your imagination. "You know, all this talk about margaritas has really got me craving for one. Let's go get one at Cesar's; they've got the best." If you're a woman, chances are you don't want to ask the guy out, but you can steer him in the right direction by guiding him — "I could really go for some ice cream right now." See? It's easy.
photo by Steve Koo
There are tons of them, literally a few every weekend throughout the entire summer. Street fests are loud, crowded, and full of stumbling drunken people. Keep the flirting high and prevalent. The goal is not to get digits; it's to head someplace else after the fest is over. (Street fests usually end at 10 or 11pm, depending on the neighborhood.) Typically you will head to the next place in a group consisting of some of your and his or her friends. Once there, you will have more space, less drunks, and less noise with which to contend. This is where you can switch conversational gears; turn the flirting down, learn more about the person, and then it will be easier to get digits.
I'm too busy playing volleyball on the beach to take any time to meet women, which is too bad, because there are tons of them out there. If looks are your thing, the beach is a great place to meet people, because you can identify fit bodies quickly, what with the minimal clothing being worn. You have to be bold and confident to approach someone on the beach, as your intentions are obvious from the start. That's the tough part. The good news is that there is no noise with which to contend and there aren't any drunken fools. Use an object to quickly and casually break the ice; this will help a lot to diffuse your obvious intentions. Last week I approached two women on the beach, who were laying out together near our volleyball courts. (All right, I guess I do meet women on the beach but it's not what you think.) They had a box of Wheat Thins on their blanket. "You better be careful with those."
"What do you mean?"
"Having those out in plain sight of a bunch of hungry volleyball players who never bring any food down with them, could be dangerous."
"Would you like some?"
I sat down and joined them for a couple handfuls of Wheat Thins and some conversation. I played a few more volleyball games and returned to their blanket intermittently, eventually giving them bookmarks advertising my book before they left. It's really not that hard. See how once I broke the ice they gave me the green light to continue by offering me some food, which was my opener? You can use any object within sight — a book, food, sun block, whatever.
The object at the beach is to get digits or, even better, relocate. Suggest going up to Castaways for a drink or to dinner somewhere. Be casual about it and don't push. Again, if you're the woman, make the suggestion, "I could really go up to Castaways for a drink." It's pretty close to inviting him, but not quite the same and he'll invite you (unless he's completely clueless, in which case you don't want to have anything to do with him anyway!).
Sports leagues are plentiful each weeknight evening throughout the summer. Dozens of teams flock to volleyball courts on the beach, softball and kickball diamonds, tennis courts, rollerblade hockey venues and even dodgeball courts. You will have little time to talk with an opponent, so keep it light and flirtatious. After the game, ask which bar his or her team goes to; if they don't go out, invite your opponent's team to join yours. Once there, you can have a conversation and work your magic.
Movies in the Park.
There are lots of movies put on by the city in various locations, the most popular spot being Grant Park. Proximity is your best friend here, as you can easily strike up a conversation with someone on a blanket or in a collapsible chair near you. "Is that wine good? I've heard good things about it but I haven't tried it yet." "Have you seen this movie before? I've seen other Hitchcock films but not this one." Again, it's easy.
Cubs games are easy places to meet people; not so much at the games but after, at the bars in Wrigleyville. Most people are at least moderately buzzed. You'll have large crowds and lots of competition with which to contend. Act quickly. I mean quickly. Get a smile, return it and approach. I go for a kiss right off the bat (pun intended), to deter the competition and gain her focus. "I'm a Sox fan but I heard Cubs fans were better kissers; is that true?" I've also had women say, "Wanna make out?" by immediately bringing up the topic of kissing and types of kisses.
photo by Tyler Coates
Another good place to meet. You'll have to act fast here, too, because I'm not talking about meeting the people in the garden; I'm talking about meeting the people walking by the garden. Sit by the sidewalk and if you catch someone's eye, quickly suggest a drink. "You look parched; have a drink before you head off to wherever you're going."
These include events like the fireworks in Grant Park and Venetian Night. Again, proximity is your friend. And again, your goal is to hit another location after the event. If you meet someone within your group, perhaps the friend of a friend, you can suggest going for a walk or get digits without having to extend your time together by hitting another event. (This is also true for movies in the park.)
That's it. See how easy it is? Really, the key is to get started. Like anything else, meeting and breaking the ice at these various Chicago summer hotspots takes practice, especially with flirting. If you start now, by the end of summer, you'll be a pro.
Comedian and advice columnist's Ian Coburn's book God is a Woman: Dating Disasters has earned great reviews from men and women alike on Amazon, where it currently rates an overall perfect review score of five stars, with 35 reviews, more than most books ever receive. The book relives Ian's hilarious misadventures in dating and sex, where Ian learned how to become quite prolific in dating. After each story, for those who want it, Ian reviews what he learned and how he put it to good use. Read it for the laughs or for the laughs and advice. Starting in June '07, Ian is a dating expert on Lifetime Television's website for women. He also writes a dating advice column entitled "Lunch is Not a Date." You may find the book in bookstores and at all online book retailers. See GodIsAWoman.net for more details.
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