A lot of young men and women enjoy the casual atmosphere of a chat room for singles because it gives them the opportunity to get to know locals and build romantic relationships one message at a time. Most chat rooms offer free registration and give singles plenty of room to maneuver. You can jump into flirty chats by choosing the right dating platform and social network. The following dating sites have live chat options to satisfy singles looking for romance online. Browse Free: View Photos Now. Zoosk is one of the most popular online dating sites around with over 40 million members to its name. Every day, Zoosk members send more than 3 million messages to one another, and many of these chats lead to real-life dates.