Contrivances

I would give him what he wants. You are right, they are contrivances, but no need to analyze it. It's normal.

This is simply being "tuned in" to those we love, and it's a lifelong occurrence.
Like when my fifteen year old daughter was freaking out about what she was going to wear to school last Friday. I'm sure it wasn't about the clothes, she was probably anxious about a presentation she had to make in class that day.
Or when my husband snaps at me over something dumb. Likely he is hungry or tired (just like a child LOL!) or worried about something at work.
People, especially young children, can't (or don't) always verbalize their feelings and fears, so they act out or express themselves in other ways.
Just continue to be sensitive to your son's needs, and don't overthink it!

Say nothing
Smile
Cuddle and coddle as much as you want and as much as he needs.

Yes indeed, young children do struggle with their roles (youngest, oldest, our baby, big boy, darling daughter, etc.). So this is typical and healthy, as they learn to be comfortable in the roles they are fully acquiring and leaving behind the ones that no longer "fit".

Two things that I've noticed. Often when a child has accomplished something (a long-awaited milestone) for which he is honestly praised, he may feel pride, but also fear that he will now always be expected to perform this milestone. Totally natural. Also, many children do better with specific praise for a deed well done (Hey, nice job with cleaning up!), with adults refraining from labelling it a "big boy" behavior, or saying "Your a big boy now." Again, this can be an overwhelming indictment from their point of view. Just my two cents. All my best.

Probably. Kids grow and develop and need reassurance that they are loved all the time. It is expressed more or less at different times. My daughter is 13, and every once in a while she will still pretend to intentionally annoy me (by getting in my space) but really, I think she just needs a hug and feels like she is too old to ask.

So, how have I handled it? I give them the affection and reassurance they are (secretly) seeking. I don't make fun, or tease. I just give hugs or whatever it is they seem to be needing.

No big deal. Maybe when he behaves this way, you could just ignore whatever he has actually said, but intervene with YOUR idea ;) and tell him that YOU (mom) need a hug, and would he mind indulging you.
:)

Kids don't always know what they want, or how to communicate it if they do know what they want. Remember they've only been on the planet a few years! When they start growing up there's a real pull between being a little kid and a big kid. And it doesn't end for a long time (when we brought our 18 yr old to college last month she told us, as we got ready to drive away, that part of her wanted to get back in the car and drive back to NY with us).

So when they're school age they begin to get a little nervous, they have needy moments that they don't even fully understand, they go through developmental growth spurts, they change just when you get used to how they were. I always tried to make sure they knew I was always there, would always be there - I'd nudge them out of the nest but assure them I'm right behind them to help them get back up when they fall - becuase they will fall. Always encourage and nudge them to try - and always be there to catch them. They figure it out. enjoy these moments - pretty soon you have to skypt to see them!

I think some of it is age. My DD used to say her tummy hurt...and that got her sent to bed.

I agree with Mamazita that part of it is being unable to say "I'm anxious" so it comes out in other ways.

he probably hasn't sussed it out either. he just knows he's uncomfortable or worried, and so has to latch onto something. grilling him won't really reach the root of the problem since cold and bugs and raindrops AREN'T the problem.
maybe it would help him if you can help pinpoint the issue. 'it's a very small bug, honey. he's not interested in you. is this slide looking kind of high? we can go look for wildflowers if you'd rather.' or 'i'm chilly too! oooooo, big hug. there! much better! oof, now you're TOO warm. off you go!' or 'sitting on my lap won't get your crayons. go over there and get the stool, you know where we keep it.'
i wouldn't deny him the comfort he needs, but keep it a brief reassurance and then help him realize that he CAN cope. and give him a smile and a brief word of congratulations (not too much!) when he does.
khairete
S.