How should I approach guy who rejected me in the past?

He told me he wasn’t in a good place to date before he got back together with his ex. Then he matched me on tinder and tapped me on Grindr a year later. We have hung 2x since. 1 time he made the comment I should post pics on a page for hot guys, but another time he told me about a guy he was dating who was not giving him enough attention and kept asking what I thought about it.