The challenge could be running across the right person at the right time since the chat room option tends to be quieter than one might expect on a site with so many users.
This site shouldn't be confused with the matchmaking site, Ok Cupid.
Some of the best reviews are associated with the site's free app (which does include in-app purchase options), Cupid Dating.
Cupid Dating is a local matchmaker that allows instant chatting.
Chat rooms for singles aren't as prevalent as they used to be.