Skip to content
Author
PUBLISHED: | UPDATED:
Getting your Trinity Audio player ready...

Last week, we introduced you to The Pick-up Artists, our crack team of hopeful romantics out on the prowl. Their mission? To check out the singles scene and report back. This week Hanna, Alex, Oliver, Cindy and Erin hit networking mixers, indie rock concerts and wine bars in search of love (or at least a date). They rated each spot’s hook-up potential, from one to four hearts.

HANNA

Howl at the Moon,

9 p.m. Saturday

If I were an old man, I would’ve had a great chance of finding love at this rowdy River North singalong saloon. There were plenty of middle-aged drunken ladies raucously giggling as the dueling pianists sang 20 different songs about small male genitalia. The closest I got to meeting someone was when I asked a cute boy standing by the bathroom what he was doing all alone, and he replied, “Waiting for my girlfriend.” Later, I thought I caught the eye of a hottie, so I gave him some non-verbal cues that I was available. Ten minutes later, I stopped sensually reapplying my lipstick when my roommate pointed out that he was making out with a girl–and I was getting gloss on my chin. 26 W. Hubbard St. 773-244-1166.

Rating: (heart heart)

ALEX

Play the Field,

6:30-11p.m. Thursday

I set out solo to the monthly Play the Field singles mixer at the Field Museum. As I walked in the door, it didn’t take me too long to realize that I was overdressed, should have brought a wingman and that getting one phone number was going to be next to impossible. The crowd was in their 20s, 30s, 40s and even 50s and wearing everything from cowboy hats to fishnet stockings. I felt like a creep walking around by myself in business casual attire. And to top it all off, 98 percent of the crowd wasn’t there to pick up or to be picked up, but to hear the entertainment, Poi Dog Pondering. I spent most of the night in futile conversations with women who wanted nothing more than for me to leave them alone so they could listen to the band. My favorite attempt of the night was Molly, a pretty thirtysomething. When I asked her why she was there, her answer was to see the band, of course. When I told her that I was there to pick up girls, she replied, “I must be a decade older than you.”

Rating: (heart)

OLIVER

Empty Bottle,

10 p.m. Friday

I’m a huge fan of dingy bars with great music, old-school Galaga machines and cheap beer. That said, I can hardly recommend the Empty Bottle as a place to meet people. When I was there Friday, the vast majority of the twentysomething crowd was there for three reasons: to see Califone, a great local band; to hang with friends; and to look like Urban Outfitters employees. Beyond that, I didn’t find much else–well, not unless I could’ve said the magic words: “I’m with the band.” While most of the female population was in the main room, drowning in a sea of alt-rock dudes, I chatted with Bianca, a tall, dark-haired student, by the pool table in a quieter room adjacent to the stage. I figured her lack of interest in the music could work to my advantage, since I have no knowledge of the local music scene. Unfortunately, her lack of interest in the music was only rivaled by her lack of interest in me. Thus, I didn’t hesitate to scamper off when my cell phone rang after midnight with an invitation to hit another bar. 1035 Western Ave. 773-276-3600.

Rating: (heart)

ERIN

Maeve,

8 p.m. Wednesday

A girlfriend and I headed to Maeve, a new neighborhood wine bar. I’ve never been much of a wine drinker, so I was intimidated by the prospect of the clientele chuckling as I naively navigated the reds and the whites. As soon as we walked in, however, I knew I had misjudged–the place was cool. With dark wood paneling, six plasma TVs tuned to ESPN and Coldplay and David Gray playing in the background, Maeve is a great compromise for sports fans and wine snobs. There were about 30 people there. I approached the only table of all guys, and let me tell you, approaching people here on a weekday takes balls of steel. It was worth it, though. They turned out to be really funny, sweet guys, and my friend and I sat with them for almost two hours until we left. While two of the guys were attached, the guy I initially chatted up was single. 1325 W. Wrightwood Ave. 773-388-3333.

Rating: (heart heart heart)

CINDY

Simon’s Tavern,

8 p.m. Sunday

My first assignment took me to this cozy dive in Andersonville for live music night. I had pictured a smoke-filled room of hardened souls listening to a world-weary Billie Holiday-esque performer, but Simon’s turned out to be a neighborhood tavern with quaint-yet-kitschy decor and a fabulously funky ’60s tribute band, The New Invaders. My friend and I situated ourselves at the bar, leaving the barstools on either side of us open. We chatted up a couple guys who sat next to us, but as soon as the band started playing, conversation became impossible. The place attracts a friendly bunch, though significantly older–most people were in their 40s. It’s never a good sign when the men you’re talking to start their sentences with “You’re too young to remember this, but . . . ” I’d go back for the music but not for the men. 5210 N. Clark St. 773-878-0894.

Rating: (heart heart)