How do you bootstrap a dating site?

If you have to convince people to join a social network, find something else to work on.

Social networks succeed when the people in the network convince other people to join.

Or to put it another way, people in the Harvard dorm joined TheFacebook in part because Mark Zuckerberg and other people on the hall were on it.

Relevant because "dating" was one of the primary uses of the early version. Facebook has since pivoted away from that as it has grown.

The general problem with ordinary dating apps is that success means two users stop using it because they leave the market.

Tinder success is because it mostly avoids this problem. On Tinder, success doesn't necessarily remove users (though I have two friends who met on Tinder and are monogamously married).

You have to grab their attention via other means. Think about what other points of interest your users have as individuals. Cater to that interest and once you have enough people then you introduce the dating app service. Else you can visit your target audience where they gather and tell them about the service and give them an incentive that will keep them interested until there enough people to make the service useful. Such as a 2 year free membership for the first 5000 users. You can also partner with another service that has the users and would want dating as a new service.

Think about what new communities are appearing on the net and create a dating service for them. What new interest have you seen growing lately?

In most chicken egg problems you have to provide either side at the start.

For example reddit got big by simply posting themselves until they had enough users posting for them and gaining traction.

It's kinda hard to do that in a dating app. Maybe that's where the bots come from.