The second one is likely just a joke.

Judging by the way everybody else is dressed they are both very dressed up.

I would say that it's his wife or girlfriend, or at least a close friend who would understand the joke.

And looking closer... is that phone even turned the right direction for taking pictures?

I don't get the first one - what's out of the ordinary of funny?
It can't be the goofy stride of the guy on the right, second row. That wouldn't be worth the effort to post it.

 

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yes it's certainly not the leonardo strutting meme that's wildly popular with today's youth.

 

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Maybe? Never heard of the "Leonardo Strutting" meme.
Latest one I'm familiar one is "arrow to the knee".


Edit: Ok, did a quick Google on "Leonardo Strutting", saw the original picture.
That top picture barely looks like him - I didn't pick him up.

 

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