Online dating, real-life meetings

Five digital dating services put the “out” back into “going out.”

MatchmakerCrazy 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.

MatchmakerGrouper
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)

MatchmakerHowAboutWe
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

MatchmakerMeetMoi
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

MatchmakerThe 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

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