Planning a date can be a difficult enough experience, let alone if you're doing it for two people that you've never met before.
Sarah Press, CEO and co-founder of Project Fixup, a Chicago-based online startup that bills itself as one part matchmaker, one part concierge, said the key to her job is creating an experience centered around common interests.
"We look at Yelp and look for feedback from our friends to find the best bars and restaurants in Chicago and focus on sending people to places we know they'd like," the 26-year-old Old Town resident said. "Even if it's not a love connection, you're still having a conversation with someone you have something in common with at a really great bar like Hopleaf or Revolution Brewery or a really great independent coffee shop that we think you'd like to discover."
So clearly all this research has had had an impact on the dating lives of both Press and her co-founder, 28-year-old Lakeview resident Alan Illing, right?
Well, yes and no.
Press, who is single herself, said she hasn't yet had a chance to enjoy the fruits of her own hard work just yet.
"Unfortunately since I'm the one who's organizing Project Fixup, it takes up all my time and I can't use it, so it's great dates, less work for everybody but me," she said, laughing.
Illing, who is in a relationship with someone he met at college, said it's helped him get out of his comfort zones when it comes to finding new places to go out.
"We peruse a number of different bars," he said. "It's been a great way to connect with the city of Chicago and explore new venues, new restaurants, new bars."
The six-month-old startup, which charges users $15 for every date they go on and offers a money back "awesomeness" guarantee, might partner with bars later on down the line to help generate additional revenue.
"Especially for the first six months, we really just focused on trying our process, setting people up on dates and seeing if they enjoyed it," Press said. "We're just starting to, now that we know our process works, we're starting to reach out to restaurants. Coming up with mutually beneficial relationships that kind help the bar, help Project Fixup and help the people that are going on dates is the way we want to pursue with that."
Project Fixup, which hasn't generated any venture capital funding yet and has 750 users, is planning on expanding beyond Chicago once they get their sea legs about them.
"Our goal is to stay focused here until the beginning of the summer," she said "Once we've gotten scale in Chicago, we'll roll out to other cities. We feel like we can kind of keep on focusing on doing what we're doing, just getting better at it, and we'll get the payoff when the time comes."
Press said the key to a successful online dating experience is to drop your guard and stop trying to be an idealized version of yourself, as some try to do initially.
"I think it's just good to be yourself and focus on fun things to talk about that you have in common," she said. "Online dating especially can put a lot of pressure on the first date because you've been messaging back and forth for awhile, you're putting a lot of buildup on it, you're hoping you make a great impression right away."
Matt Linder is a RedEye special contributor.
Want more? Discuss this article and others on RedEye's Facebook page.