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Mate & switch
Five singles looking to up their dating game get a top-to-bottom makeover from our panel of experts
February 2-9, 2006 Issue
By Annette Ferrara
Name: Ralph
Age: 32
Lives: Humboldt Park
Seeks: A 30-plus smart, creative woman who "has a booming system-I mean, both woofers and tweeters-and the libido of a 16-year-old boy."
Suit up
In his own words: A stylish DJ and musician, Ralph goes by the professional moniker Major Taylor and sings and plays guitar in the reggae-punk group the Jai-Alai Savant. He describes his look as "retro-modernist-punk-yuppie-emo-thug."
TOC's tips: We couldn't argue with Ralph's tight, eclectic fashion sense, but felt he should tame his four-months-overgrown beard into a tighter, more complimentary, face-framing shape. Ralph's date-night fashion remains an individual mix of vintage and trendy pieces, but his suit-previously wadded up into a ball at the bottom of his closet-was given a good pressing. Guys like Ralph who enjoy wearing thrift-store scores would do well to heed the advice of Jeff Worth and Ralph Fasano: "There's a difference between vintage and old. It's one thing to wear something grandpa might have worn and smelling like grandpa."
Stay dry
In his own words: "I spend too much time spinning in hipster bars; I'm not meeting enough black people. I'd like to meet more women who love to go out but who don't drink, because I don't drink."
TOC's tips: While Ralph is obviously out-going, Rachel Begelman felt his over-the-top personality masks his desire to have a deep connection, and could be a turnoff. If he wants to meet artsy women who don't drink, he should look outside of bars and try Latin Street Dancing's events (312-427-2572, www.latinstreetdancing.com) , which attract a diverse crowd and take place in a smoke- and booze-free environment. The W Hotel (644 N Lake Shore Dr, 312-943-9200) offers social events (there's a chocolate tasting on February 13) that draws women in their twenties and thirties. As for his desire to find a lady with "a booming system," a teen's sex drive, and brains, Begelman laughs: "He's identified every guy's wet dream. Good luck!"
Go global
In his own words: "I'd like to learn how to speak other languages, and I'm [into] Vietnamese food-anything spicy. I don't care where as long as there's food involved and we go dutch, 'cause I'm broke."
TOC's tips: Learning other languages is a great, alcohol-free way to meet ladies. Try Goethe-Institut for German (150 N Michigan Ave, 312-263-0472), Istituto Italiano di Cultura for Italian (500 N Michigan Ave, suite 1450, 312-822-9545) and Japan America Society of Chicago for Japanese (20 N Clark St, suite 750, 312-263-3049). Since he's low on cashola, we suggest going to the free days at Shedd Aquarium (1200 S Lake Shore Dr, 312-939-2438) on Mondays or Tuesdays. Since he's into music and spicy food, a good date spot is Rodan (1530 N Milwaukee Ave, 773-276-7036), which has affordable Latin/ Southeast Asian fare. Or he could try TAC Quick Thai Kitchen (3930 N Sheridan Rd, 773-327-5253), which has a minimal atmosphere and plays techno-unusual for a little ethnic place. Our female experts all agreed that despite his bank balance, he should treat-at least on the first date.
Get outta the club
In his own words: "Gregarious would be an understatement-I'll talk to anybody-but I'm bad with the follow-through. I have a lot of trouble reading women, so unless they wear a sign that says i am attracted to you, moron! in big-ass neon letters, I'm clueless."
TOC's tips: While Ralph doesn't seem to have any problems approaching women, Begelman advises that he needs to "work harder on communicating with women and not just hooking up with them," and that's easier to do outside of a dance-club or bar environment.
Interested? Find out more by e-mailing ralph@timeoutchicago.com.
Name: Neha
Age: 24
Lives: Gold Coast
Seeks: "Well-rounded, intelligent guy in his mid- to late twenties who is sporty, spontaneous, has a good sense of humor and likes to learn new things."
Dress to impress
In her own words: "I wear a lot of black on black. On a casual date, I'd probably wear pants or a skirt with a black top and heels." A busy student in her last year of medical school, Neha spends most of her waking hours studying at Old Town's 24-hour Starbucks, and puts her long, raven hair up in a ponytail much of the time. However, she enjoys getting dressed up and accessorizing, and can navigate quite well on three-inch heels.
TOC's tips: To give Neha a boost-literally, in terms of height, and metaphorically, in terms of confidence level-we put her in heels and picked a form-fitting, flowy jersey dress in emerald-green to help her stand out from the crowd, and accented the outfit with a copper bag and a necklace, worn as a bracelet.
Leave the lattes behind
In her own words: "I hardly go anywhere for the specific purpose of meeting people."
TOC's tips: Having Starbucks at the epicenter of her social life, according to Obi Nwazota, pretty much nixes her chances of meeting an adventurous guy. Stephanie Leese thinks Neha should check out one of the city's "culture clubs" for young singles. The Field Museum (1400 S Lake Shore Dr, 312-922-9410) has Play the Field, and then there's the newest addition to the scene, the Loyola Museum of Art's ArtSmart (820 N Michigan Ave, 312-915-7600). Since Neha loves trying new sports and is into ethnic foods, she could try online meet-ups like Chicago Sport and Social Club (http://www.chicagosportandsocialclub.com); go out for interactive food like Korean barbecue (both San Soo Gap San, 5247 N Western Ave, 773-334-1589; and Hae Woon Dae, 6240 N California Ave, 773-764-8018, are great); and satisfy her sweet tooth at Bucktown's HotChocolate (1747 N Damen Ave, 773-489-1747), where guys hang out for the artisanal beers.
Broaden your horizons
In her own words: "I've never taken the opportunity to learn about the stuff Chicago is known for, like blues and jazz, and I want to learn more about reggae, house and reggaeton. I'm also curious about theater and art."
TOC's tips: Catching a play at a storefront theater like the Viaduct (3111 N Western Ave, 773-296-6024) or the Side Studio (1520 W Jarvis Ave, 773-973-2150) could be fun. On the music front, Neha would do well to venture out of the Gold Coast. Lee's Unleaded Blues (7401 S South Chicago Ave, 773-493-3477) on the South Side has an after-work mixer on the first Friday of every month, and the Green Mill (4802 N Broadway, 773-878-5552) is a legendary jazz spot that's dimly lit and swanky (skip the Patricia Barber and Kurt Elling nights-they're packed with couples). For old-school reggae and dancehall, try Sundays at Sonotheque (1444 W Chicago Ave, 312-226-7600), when DJ Rik Shaw spins hollaworthy sets.
Do something active
In her own words: "When I go out on dates, there are often awkward silences. I tend not to make the first move, but I'm always impressed by someone courageous enough to strike up a conversation."
TOC's tips: Neha won't have to make the first move at the Museum of Contemporary Art's First Fridays (220 E Chicago Ave, 312-280-2660), which are packed with singles; or Saturday salsa nights at Rumba (351 W Hubbard St, 312-222-1226), where she's guaranteed to be pulled onto the dance floor. To get her confidence up, Niki Lindgren suggests "going out on a date with a nothing-to-lose attitude."
Interested? Find out more by e-mailing neha@timeoutchicago.com.
Name: Elizabeth
Age: 24
Lives: Bucktown
Seeks: Twentysomething creative hipster
Flatter your figure
In her own words: "I go for quasi-artsy comfortable. Usually I wear dressy pants with a silly T-shirt and pointy shoes."
TOC's tips: Petite Elizabeth's got great curves, but her black sweater/flat shoes/jeans combo wasn't as flattering as this vintage wrap dress, which has the bonus of being extremely comfortable. Since Elizabeth doesn't normally wear heels but would do well to gain a few inches, we put her in stacked wedge suede shoes, which are easier to walk in than regular heels, look retro-fab with the dress and give a good curve to her calves. Regarding her predilection for "silly T-shirts," we advise keeping those at home, along with her shyness.
Take it online
In her own words: "It's highly unlikely that I'll meet someone interesting at the elementary school where I teach-most of my colleagues are middle-aged women!"
TOC's tips: Elizabeth mentioned that she's tried online dating before, with mixed results. Begelman encourages her to keep it up in spite of her frustrations with the process. It's a great forum for meeting new people, especially since she's not meeting any guys at work. Since Elizabeth is most comfortable meeting men through her friends, Leese suggests she initiate a personal campaign: challenging her friends to introduce her to as many single dudes as possible (kind of like an NPR fund-raiser, but with men, not money).
Plug in
In her own words: "I would love to learn to cook and want someone to introduce me to new music, new books and new neighborhoods in the city."
TOC's tips: Most cooking schools around town are pricey, but Gallery 37's World Kitchen (66 E Randolph St, 312-744-8925) offers classes where you can eat what you make, so for $30 Elizabeth can get cooking instruction and dinner. To meet bookish types, Elizabeth could head over to the MCA's (220 E Chicago Ave, 312-280-2660) Free Tuesdays Literary Gangs of Chicago series or pop into Danny's (1951 W Dickens Ave, 773-489-6457) for its reading series-the bar is in her neighborhood and is crowded enough that it's nearly impossible not to meet someone. For good music on a small budget, alt-country hangout the Horseshoe (4115 N Lincoln Ave, 773-549-9292) hosts quarter-beer night on Tuesdays with the Siderunners; the Charleston (2076 N Hoyne Ave, 773-489-4757), Empty Bottle (1035 N Western Ave, 773-276-3600) and Hungry Brain (2319 W Belmont Ave, 773-935-2118) all have jammin' jazz nights that attract younger, hipster crowds; and the Chicago Cultural Center (78 E Washington St, 312-744-6630) has free weekly music concerts.
Learn to flirt
In her own words: "I am definitely no pro at striking up conversations with people I don't know at all."
TOC's tips: To sharpen Elizabeth's conversational skills, she should take a class on flirting at Early to Bed (5232 N Sheridan Rd, 773-271-1219). The woman-owned adult toy store also holds classes on how to be better in the sack, but first things first. Since Elizabeth also told us she digs taking photographs with her new camera, Leese suggests she take it with her when she goes out and ask handsome lads if she can take their picture. Most men don't mind having their picture taken, and it's a good excuse to start chatting with someone.
Interested? Find out more by e-mailing elizabeth@timeout chicago.com.
Name: Brian
Age: 38
Lives: Roscoe Village
Seeks: "Gay male who is a combination of Brett Favre and Anderson Cooper and has big-city sophistication with a Midwestern sensibility."
Going-out style
In his own words: "I try for urban casual, but I'm not sure I always get there."
TOC's tips: At 38, Brian should have his signature look down, says Leese. She suggests picking the brain of any of the personal shoppers in town if he's not particular about designers or a look. Worth and Fasano caution that he should "never, ever, ever wear anything with a swoosh or a team logo on a first date. Dating is for men, not boys." To tighten and update Brian's look, we put him in darker, low-rise jeans, a slim, tailored jacket with a neater shoulder line and a double-vented back and a cool mint-green T-shirt (for a more updated, casual-date feel).
Don't waste time
In his own words: "I love to attend social galas, but I tend to meet men who live in other cities and who are both emotionally and geographically unavailable. The 22-year-olds aren't looking at me anymore."
TOC's tips: As an event planner, Brian's social calendar is full of charity events. But when he's looking for love, he heads to predictable gay-boy haunts (and we do mean "boy") like Sidetrack, and hotel bars like the one at the Peninsula (which naturally attracts out-of-towners). All of our experts agree it's a plus that he's so busy, but he needs to move beyond his typical hangouts or, as Leese suggests: "Think globally. Act locally." He could volunteer as an usher at Columbia College's Dance Center (1306 S Michigan Ave, 312-344-8300), and interact with the cultured gay men who attend its modern-dance performances. Or he could check out the men's film nights at Gerber/Hart Library (1127 W Granville Ave, 773-381-8030), a venerable gay and lesbian library and archive; or go to the monthly wine-tasting events at Kafka (3325 N Halsted St, 773-975-9463) or at Gourmet Grape (3530 N Halsted St, 773-388-0942).
Ogle art
In his own words: "I'd like to learn more about art history, Chicago architecture, and local galleries and artists. I would love to see Chicago through someone else's eyes and perspective."
TOC's tips: The perfect first-date activity for Brian is visiting the Chicago Architecture Foundation's (224 S Michigan Ave, 312-922-3432) architectural boat tour or taking a walking tour of IIT (3360 S State St, 312-567-3000). The Art Institute of Chicago (111 S Michigan Ave, 312-443-3600) offers classes and art encounters for members and the public, and the Oriental Institute Museum (1155 E 58th St, 773-702-9520) regularly presents lectures followed by wine and cheese-and the opportunity to chat with brainy archaeology grad students. If he insists on hanging out at hotel bars, Leese recommends asking the bartenders "when the locals are there. [They] know all and they're very discreet."
Turn on the southern charm
In his own words: "I'm outgoing in groups but I tend to get shy one-on-one, especially if I like the person."
TOC's tips: Begelman says being active in his life makes Brian more attractive, but she cautions that he might be too busy to properly pay attention to fostering a relationship. Since Brian's from the South, Leese suggests planning a Kentucky Derby party at home, and asking each guest to bring three new men for him to meet. Our Check Out editors suggest he sport an interesting accessory-a watch, ring or tie. His date might ask about it, which can provide small-talk filler if Brian gets shy.
Interested? Find out more by e-mailing brian@timeoutchicago.com.
Name: Heather
Age: 28
Lives: Andersonville
Seeks: Well-traveled, down-to-earth yet adventurous man in his late twenties to early thirties
Strut your stuff
In her own words: "I'm very casual-but not Ôboring' casual. [On a first date, I] usually wear a black tight sweater, nice jeans, black boots, [and] no or little jewelry."
TOC's tips: A paralegal by day and an actress and comedian by night, Heather is a multifaceted, multitalented woman, but her first-date outfit plays it a little too safe. Tight sweaters and jeans are good, but predictable. We found a flirty, flattering silk dress with a lace pattern and paired it with a vintage-looking necklace, which she's wearing as a bracelet. A metallic suede clutch and retro-looking shoes complete the outfit. Since Heather is a natural beauty with gorgeous skin and large eyes, we took her makeup down a notch, but maxed out her lashes.
Don't jump to conclusions
In her own words: "Nobody wants to commit anymore. I'm not talking marriage, but just basic exclusivity in dating." TOC's tips: "Men do want commitments, but usually only after they've gotten to know you and experienced how wonderful you are," Begelman says. Nwazota agrees that she shouldn't assume all men are commitmentphobes: "She needs to push suppositions aside and leave a margin of error." Heather's hangouts tend to center around her Andersonville neighborhood (Kopi CafŽ, Simon's Tavern, Hopleaf), which Nwazota thinks is a bad idea. "She's stuck in a routine. She moved to Chicago for a reason-she needs to get out and explore different neighborhoods."
Explore other communities
In her own words: "I'm a big traveler and belong to a volleyball club. I'd like to learn more about the music, art and political scenes here."
TOC's tips: Art walks and gallery openings were made for Heather. Many galleries open their doors after work on Fridays, and most of them are listed in TOC's Art & Design listings. Since she's into travel, she should join the Geographic Society of Chicago (847-251-1400, www.geographicsociety.org. It's a fairly serious travel and culture group with events that are open to all. If she wants to brush up on her political punditry, the Chicago Council on Foreign Relations (332 S Michigan Ave, 312-726-3860) has weekly lectures by the big guns of international politics. For music, the Chicago Symphony Orchestra's (220 S Michigan Ave, 312-294-300) MusicNOW concerts, and the receptions that follow, draw a pretty young crowd.
And Heather could expand her athletic horizons by joining a group like the Chicagoland Bicycle Federation (9 W Hubbard St, 312-427-3325). If she's up for trying a new sport, she can drop into a pickup basketball game at the Lake View YMCA (3333 N Marshfield Ave, 773-248-3333), where there's always a friendly game going on at the upstairs court.
Take the first step
In her own words: "I'm terrible at picking up men and I rarely, if ever, go up to a man first. If I just have to meet a guy, I tend to be very honest with him and say, ÔHi. You're very cute and I want to know who you are. I'm Heather.' It either works or it doesn't."
TOC's tips: Our experts applauded Heather for her risk-taking conversation starter and encouraged her to keep it up. "It's great that she's taking the bull by the horns," Nwazota says. To knock down any inhibitions she might still have, she should sign up at the Second City Training Center (1616 N Wells St, 312-664-4032) for improv classes.
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