Dating is hard. Building a dating app might be harder.
Large players dominate the space, with Match Group---owner of Match.com, Tinder, OkCupid, Plenty of Fish and others---owning 25 percent of the online dating market share. eHarmony is the second-largest brand with around 12 percent.
That still leaves room for competition though, and online dating apps like Bumble, Grindr, Christian Mingle and Coffee Meets Bagel have found success with digitally naive singles. And upstarts like The League and Clover show there's room for younger brands, too.
But in Chicago, many dating apps have struggled to connect with those looking for love. Chicagoan Sam Yagan co-founded OkCupid and was the CEO of Match Group for four years, but that's about as close as any Chicago founder has come to finding breakout success in the dating app game (OkCupid is based in New York).
At the risk of being a bummer this Valentine's Day, we've compiled a list of six Chicago dating apps that have come and gone. From an app that tried to match PokemonGo players, to a dating app for high schoolers, here are some of the startups that tried to find a love connection in Chicago.
Project Fixup
Project Fixup, a member of the 2013 Techstars Chicago cohort, created a dating service that set up offline dates. It's goal was to create tailored dates that help people with similar interests do something fun together offline, in the real world. Founded in 2012, the startup raised $100,000 in funding, according to Crunchbase.
PokeDates
Launched by Project Fixup, PokeDates was a dating service created specifically for PokemonGo users. Similar to Project Fixup, PokeDates used specialists who matched daters with other singles who had similar preferences and liked playing PokemonGo. From there, specialists selected a PokeGym or PokeStop for the couple to meet.
helloTruly
helloTruly, founded in 2016 by father-and-son team Andy and Jack Kenoe, described itself as a “digital icebreaker” that focused on connecting people in physical spaces like coffee shops and bars. The app used push notifications to alert a person when another helloTruly user was in the same location and matched with their set preferences.
Kiss
Kiss, founded in 2015 by then-16-year-old Samuel Lurye, was a dating app for high schoolers that took the awkwardness out of asking someone on a date. Kiss allows users send a digital “Kiss” to a friend, which was essentially an anonymous message that includes a picture of the user and of two other people. The receiver---not knowing who of the three the message came from---selected the person they were interested in. The app was a way of letting the sender know if their crush was interested in them as well. The startup was part of Chicago accelerator Catapult as well as Endevvr, an Atlanta-based summer program that helps high school students launch startups.
Go Dutch Today
Go Dutch Today was a dating app and bill-splitting feature that allowed users to split the cost of a date beforehand. The app's goal was to take away the awkward tension of deciding who will pay the bill on a date. It won $2,500 after placing first in the 2015 South Side Pitch competition.
Waave
Waave was an app that included features that provided women with additional safety and privacy controls. It allowed users to check in at live events, and they could see all other Wavve users of the opposite gender who also checked, giving people an ice breaker before meeting.
