Matchmaker Crazy Blind Date
Best for Singles with crazy-packed schedules
How it works Get started on OkCupid’s new spontaneous spin-off by downloading the app (available for iPhone and Android). The app scrambles your uploaded pic to keep you anonymous-ish. Input your demographics or link to your existing OkCupid account for better matches. Select some possible times and places, and the app alerts you with compatible singles who can meet. One hour before the date, a chat window appears in the app so you and your mystery match can confirm the deets.
Cost Free. Sending a post-date “kudos”—the service’s rating system for daters—costs 99 cents and is integrated into OkCupid. But be careful: If your date is a catch, you don’t want to broadcast it to other singles.
Best for Breaking the ice
How it works This “social club” of dating services works on the Spice Girls principle: If you wanna be my lover, you gotta get with my friends. When you sign up online, Grouper gets access to your Facebook page. After scouring your info section, likes and tagged photos, Grouper e-mails you and your potential match with a date, time and reserved table at a local hot spot. You bring two friends, your date brings two friends, and the six of you meet over drinks.
Cost $20 per date per person (plus any gratuity you tack on in advance)
Best for Completing your Chicago bucket list
How it works Fill out some quirky prompts (“What would I bring to show and tell?”) and complete the sentence “How about we…” with a dream date you’d like to go on. Browse what others have posted. By dealing in cream-of-the-crop hypothetical scenarios, you’ll never again find yourself at a Wendy’s drive-through on the date from hell (unless a junior bacon cheeseburger is your idea of romance heaven).
Cost $8–$35 monthly membership
Best for Spur-of-the-moment singles
How it works The location-based app alerts you when matches—based on education, interests and how you describe your ideal mate—are in the same area. It sends an introduction to both singles. If you like what you see, accept the intro and you two can then chat to arrange a meet-up. Out with a friend? Invite him or her along, and MeetMoi will make introductions to other groups nearby.
Cost Free; upgrade features $4.99 to $19.99 per month
Matchmaker The Stir
Best for Winning the odds game
How it works Match.com hosts events downtown and in the ’burbs (rooftop bar nights, sushi-making classes, bowling) where users can meet other local singles. About 25 to 200 people show up, and most of the shindigs allow you to bring a nonsubscriber wingman (or wingwoman). A big plus: The organizers enforce gender ratios to prevent sausage fests. Next on the Stir calendar is “It Takes Two to Tango” dance lessons at Fred Astaire Dance Studios on Saturday 9.
Cost Varies per event; must be a Match.com subscriber