I want to reconnect with an old friends with benefits as we are both single again. Do I keep trying?

he’s friendly/flirty in person but won’t reply to messages. Is he keen? Do I keep trying?

Been on/off friends with benefits for years, just want the same setup we had last time. How forward can I be without freaking him out?

I want to reconnect with an old friends with benefits as we are both single again. Do I keep trying?
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