[chirp_users] Uv5r question

My buddy and I just purchased baofeng uv5r radios, we have them programmed using chirp, we were trying to hit a repeater in the middle of us, about 23 miles total so maybe 11 miles from each of us. Sometimes he could hear me but I couldn't hear him, then I could hear him and he couldn't hear me, is this an antenna issue ? We are using the rubber duckies that came with them, I also saw a setting for repeaters delay on the settings section, it is set to off, does that need to be changed ? Thankyou ken