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Dear Anna,

Other than online, can you suggest where a 49-year-old lesbian African-American can find decent companionship here in Chicago? I’m a little rusty on the dating scene. Thanks in advance. Love your column! —Open-Minded

Dear OM,

What’s worked for you in the past in terms of meeting women? Can you replicate it? If not, I’d try Meetup groups—technically you need the internet for this, but it’s not, like, Grindr. A quick scan of Chicago-related lesbian groups yielded dinner parties, outdoorsy stuff, “lesbians who love fishing,” a 45 and over group, the “awkward queer women of color group” and, perhaps unsurprisingly, a drumming circle. Peruse the groups that interest you and then go wet your whistle! (I mean that both in a sexual and non-sexual way!) Even if you don’t find your soul mate in the “Lesbian First Time Home Buyers” group, you could meet a friend who knows a friend who might be perfect for you.

Speaking of, friends of friends make excellent “companionship” partners. But bypass the whole “ask a friend to set you up” awkwardness and make it casual. Invite your friends over for dinner or a movie or Triscuits and Trivial Pursuit night, and encourage them to bring people they think you’d get along with. This isn’t an explicitly romantic route, of course, but it’s all in the favor of bringing new people into your social circle. Change your routine. Be social. Go to new places. Say yes.

And part of that involves … trying online dating.

I know. It’s scary. It’s not what you’re used to. But also: It’s free. It’s convenient. It’s open 24/7. And you don’t have to host 20 cheese and gherkin parties and cross your fingers that your new girlfriend will show up to one of them.

Part of de-rusting yourself in the dating scene means going out of your comfort zone and trying experiences that are new and strange and maybe even terrifying. But doing them anyway. Because that’s where change and transformation and bliss happen—right after the horrible scary things.

At the end of the day, it’s not about where to meet people. It’s about opportunity. Are you willing to go through a little pain or awkwardness for the opportunity of finding some long-term happiness? Maybe you’re not there yet, and you should try those social and cultural activities mentioned above first. But I would also encourage you to harness all the opportunities that are available to you—even if it means dipping a toe into unfamiliar territory. As Helen Keller said, “Life is either a daring adventure or nothing.”

Good luck, OM. If you do make an online profile, send me a link.

Anna Pulley is a RedEye contributor. Want to ask Anna an anonymous question about love, sex or dating? Send it below, or email [email protected].

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