Sarah, 25, has had just one date in three years.
“Douche bags and old guys. That’s all I get.”
Sarah, an actress from Lincoln Park, punctuates her declaration with the last gulp of her white wine, which is quickly replenished by the extremely attentive bartender at PJ Clarke’s. “I’m a single girl and I do get hit on, but not by anyone I’m going to date.”
Moments later, a silver-haired man old enough to be our father plants himself between us, leans in uncomfortably close and stares at Sarah expectantly. She shoots me an I-told-you-so look and turns to the stranger, “Can I help you?”
Fifteen minutes later, confident Sarah has politely but firmly dismissed the unwanted visitor, and I’m mentally thumbing through a Rolodex of guys to fix her up with, even as she tells me of her mother’s recent failed attempt. (“Apparently, being single is my mom’s only requirement.”)
It’s hard to believe she has trouble dating. Dressed in fitted dark jeans that show off her mile-long legs and a short-sleeved white fringe top, Sarah towers over me at 5'10" (6'1" counting the heels). But there’s something intimidating about a tall, confident woman, especially one with Sarah’s loud voice and occasional feistiness. “I probably can be a little too in-your-face. My bark is way worse than my bite,” she admits, and then smiles. “But I bark a lot.”
She points to her height as a dating roadblock; she won’t date anyone shorter than her. Her other rules: She prefers sports fans (“I’m a die-hard, to the end, Yankees fan. I bleed pinstripes.”) and refuses to date other actors (“Actors are like a Venus flytrap for women because they’re naturally charismatic and usually attractive, and they crave attention. So they’ll be whomever you want them to be, not who they really are.”).
Sarah moved here from New York City in November, knowing only a couple of people. In New York, she had a close-knit group of friends, most involved in performing arts as well. Because she tries to stay clear of dating other artists, she just didn’t date.
“I’m a completely in-charge person and I will control a situation if you let me. But really, I’d just rather be with someone who can control it better,” she says. “And most of those guys, like starving artists, are too passive.”
Coming to Chicago was an opportunity for Sarah to start fresh, both professionally (Stewart Talent represents her) and personally (a messy breakup with her college boyfriend three years ago really tripped her up). But for the last few months, Sarah hasn’t had much luck meeting anyone—friends or dates. Looking around the Division and Clark–area bar we’re sitting in, she contemplates that maybe she’s just hanging out in all the wrong places.
When Sarah tells Steinmetz about her skeevy experiences at Viagra Triangle bars, Steinmetz agrees she needs to ditch that ’hood. Instead, she suggests areas such as Wicker Park, Uptown and Lakeview, where the crowd is typically older than the average frat boy, as well as more successful and diverse. Steinmetz also advises her to not apologize for dismissing shorter men. “That is not a prejudice. That is something that makes you uncomfortable. We all have our deal breakers,” she says.
LET’S TRY THIS AGAIN
We take Steinmetz’s location advice and head to a known meat market in River North—Bull & Bear. Surveying the scene, we see a lot of financial types in suits. But Sarah points out a few guys, including the bartender, who could be her type—burly and rugged (“Think lumberjacks—the kind of guy who will drink a beer and then smash the can on his head.”). She’s hesitant to approach anyone, until I remind her that Steinmetz said she can initiate conversation without asking someone out.
After draining her martini, Sarah taps on an attractive guy’s shoulder and asks if she can squeeze through to order another drink at the bar. That’s all it takes. Moments later, she and Billy are playing 20 questions.
“I was a starving artist in New York and then I got a better offer to be a starving artist here in Chicago, so I moved,” she explains.
“So, you’re not so starving anymore?” Billy jokes.
“Oh no, I’m still starving. But it’s good for my figure,” Sarah quips with a sly smile.
Exuding confidence and keeping her aggressiveness in check, Sarah chats with Billy for another hour, and another martini. As we leave, Billy asks for her phone number.
Three days later, he asks her out via text message. Although not exactly her dream guy (Sarah says the texting approach was lame and, sorry buddy, but I gotta agree), at least Billy wasn’t a douche bag or too old—and it’s her first date in more than a year and a half.
Want to date Sarah? E-mail firstname.lastname@example.org.
FAMILY & FRIENDS
“She’s an actress so sometimes when she tells stories, she likes to exaggerate.” —Emily, sister
“She’s very outwardly confident and loud. Some guys respect that.” —Dan, sister’s boyfriend
“She’s got the dramatic part. She needs somebody who has their feet on the ground. She’s very articulate. She loves to explore things. She needs somebody who can keep up with her. She likes guy-guys.” —Susan, mom
“I did see a guy get her number, but then she said it didn’t go anywhere and that she thought he was gay.” —Isaac, friend “She was afraid to go out and meet anyone new. She was stuck in her circle of friends. Moving to Chicago is a big step forward for her. And now she needs to get out there.” —Susan, mom
DATING COACH ADVICE ON...EXPANDING YOUR SOCIAL CIRCLE
If you’re new in town or just don’t know a lot of people, try sites like meetin.org, which is like a dating site without the dating—one of the few rules of the organization is to not hit on anyone. This site is purely for meeting new friends and going to events together.
Ditch the bars and try events like First Fridays at the Museum of Contemporary Art. Although not touted as a singles event, it’s a great opportunity for mingling with peers and possibly making a connection.