Dog cries, what to do?

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I have 2 dogs. One I got when she was 3 months old called India and is now 6 years old, she is almost perfect. A bit more training I wouldn't have a single complaint. Another I got from a rescue when he was 10 months old and he is now 3.5 years old, his name is Boss. When I went to go see Boss at the rescue I took India with me, he had a muzzle on his kennel and I was told he was extremely aggressive towards people and dogs and they warned me they werent liable if he attacked my dog. Turns out everything they told me was a lie. He has never gone after a dog and infact he would rather run away than fight, he is also the biggest love bug in the world and has never gone after a person. If anything I trust him more around dogs than India as India will react to a dogs bad energy and Boss won't.

ANYWAY, my issue is this. Boss cries if we go on a walk and we sit down on a bench for literally 10 seconds he cries and cries and whinges and whinges, I'm pretty sure he's telling me he's bored of sitting and wants to walk but it would be nice if we could just relax as I live by the sea and sometimes I just want to sit down and look at the ocean. I would like to be able to go to a restaurant by the marina and have a drink with them but I know Boss will disturb everyone else there. He cries for attention and although I never give in when he cries and only give him attention when he's relaxed he still does it. Strangely he also cries after a walk, even if he's exhausted he will lay down and cry a couple of times. It seems the amount or intensity of exercise makes no difference to him crying. My main issue is the first one, it's one that affects my ability to socialize as I'd rather be with my dogs than without them. He's not high strung either, he's pretty chill and listens well on and off lead, in the house and out so I don't know what I'm doing wrong. The only time he goes into "go mode" is when someone walks past the gate but as I live in a place with a lot of addicts and dangerous characters I don't mind him protecting the house and he stops when I tell him to. He actually stopped me from being burgled when I first moved in. I have taken him to the vet for an unrelated reason and while he was there had a full checkup and nothing wrong was found so he's not injured, he's done this ever since I've had him

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