If he only watches carefully as you handle the hens and if you keep calm and keep the hen calm and put her back down...he'll know you're not hurting them and will probably accept it without attack. I handle my hens regularly, pick them up keeping everyone calm and putting them back down pretty after just a few minutes, in front of the rooster and he keeps watch but accepts it without too much concern. Works for me, but keep your eyes peeled and a check on your emotions around him.
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I'm going to agree here with aart. Being calm, confident, cautious and consistent is the very best way to deal with impressionable cockerels.
Everyone deals with roosters differently, has different experiences, and has different ideas on how to deal with behaviors. We have found fear inducing treatments just do not work for our situation. We only want friendly roosters, so we don't have to worry about bad behavior later on, so we work with our males. Socialize daily, and always monitor them anyway.
We have many roosters... but, the first thing and main thing I usually do is calmly and gently make sure everyone is calm when they are being held and put back down after being held. Speak calmly and softly, so they have to stop fussing to hear what you say. I also put cockerels all in with a stable, well-balanced adult rooster. And this helps. We've only had one male early on that was a hand biter. He was a hatchery PR RIR. He tested us during his juvie stage, but, outgrew the phase once he realized biting didn't faze us. He never escalated as everyone stayed calm and never rewarded that behavior, nor reacted with fear. He never learned to act reactive and fearful. Again, some would disagree, I'm just letting you know what's worked for us.
To me, I also think it may be
possible your male may possibly be showing interest in you for attention... and you might not realize that is what he possibly may be doing, as most roosters are not generally known to be seeking attention. Usually the males who have the best, and gentle looking eye contact with me are the ones who are most often the friendliest. When he's coming for treats during the swarm he is showing he likes the positive interaction. He may just be unsure of you, or the rake, etc.
Some roosters actually seek attention... like the poster's rooster who rooster follows them like a puppy and looks in the window. I bet he is a really sweet rooster who probably looks forward to their interactions. Friendly roosters are not usually the norm, so often times this behavior can be mistaken if he hasn't been well socialized. But, if he likes you, but, is fearful, he may do experimental pecks or tugs on your clothing to get your attention. (Just a possibility to rule out.) We have one male who is right now crowing at the back door for treats, lol. He may be training me... but, he is communicating- in his way.
We have a few that will asked to be picked up. There is one freeranger who will tug on your pantleg, and sometimes accidentally grab your skin. My husband occasionally swats at this male, but, I ask him to refrain and not teach him that he should be afraid, as the rooster's not showing aggressive behavior... actually the opposite. He's friendly, sociable, affectionate, and enjoys occasional companionship of humans. How do I know? You hold him, he closes his eyes, smiles, and falls asleep. It's trustful. And I can take him in any pen even with males without their acting up.
However, any male that wing dances around you or offers fake tidbits is one that should be very closely monitored- a male like this is a completely different story. Also, some aggressiveness can be genetic, but honestly, I don't think I'm hearing that here.
I'm just perhaps suggesting, try occasionally gently picking your boy up and talk soothingly to him, after a bit, gently put him down facing away from you. Offer him a treat. See how he reacts. A balanced rooster should walk off a few steps, then, come back and take the treat, or, offer it to his girls, and hope for more. lol Anyone who wing dances, or, tidbits is not well balanced. If he doesn't respond, or escalates, or becomes aggressive, rehome (to someone experienced, fully knowing the situation) or culled.
Just be very careful and watchful.
I've had fully grown "wild" unsocialized roosters, and within a short time are friendly. He may surprise you.