You can't. If they remain a watcher and you send an offer that they either decline or it times out, you can't send a "new" offer to them unless they unwatch/rewatch it or they send you a message, where you can respond with an offer.
....... "The Ranger isn't gonna like it Yogi"......... Boo-Boo knew what he was talking about!
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Yes, I have no Bananas, only Flamethrowers.......