Easily upset 7 year old boy

DS has always gotten upset over things, but the last few months it seems to be happening more often and he's getting upset over the same things over and over again.

- In October or November, a girl thew his lunch box in the bin & he seemed unphased until he realized that his Monsters' University cooler bag was gone (& the replacement I bought wasn't the same style). He's burst into tears over that multiple times, most recently last week. He went through 3 lunch boxes in three weeks & that's the only one he blamed on someone else, I suspect maybe one or both of the other breakages was due to other kids & I was frustrated & went on about it a bit.
- Last day of school he was eating ice cream at after school care & cried because he's going to miss year one & his teacher (I don't know why if the kids throw his lunch box away and his teacher was difficult to communicate with (that may be my issue))
- DH got a new company car & he's cried over that a number of times too - "I just miss Kade (that's what he named the old car) so much"
- he's upset by the new year, he wishes it was still 2013. I've explained that a year is just the amount of time for the earth to go around the sun and that time moves at one second per second, used Star Wars & Doctor Who quotes to no avail.

He really doesn't like change! I want him to do an after school activity, but can't convince him to do it - I've suggested karate, Cubs & drama classes.

Is it normal for 7 year olds to be like this? What can I do to help him?
Thanks for your help.

How do you help him deal with his upset and the transitions?

I say this because I have a similar boy and we have to give a good lead-in to transitions, make new things normal by stories etc at home before hand (and he was just signed up to the local scouting group - that wasn't optional!), say that it's OK to be upset. He still misses my old car too and talks about Victor (which was odd, as Victor was my commuting car so he was rarely in him). We had 15 minutes of tears when Patrick left Strictly Come Dancing. He's been in tears about someone in his class saying that he likes tomatoes when he doesn't and won't stop going on at him about it. He refuses to do sport clubs or music lessons - he did do French for a year but found it too easy so started messing around and was asked to leave the class: I am still furious about that, months later!

I give lots of reassurance, sometimes have a cry with him to show that it's OK (he has ended up crying about crying before) and long, long lead-ins. His school is changing next year (moving up a school) and we've already been for visits and discussed with the next head the month-long transition period. His school (this one and the next) are really big on proper transitions with lots of meeting the new teacher, new classroom and even the new school so they are settled. We've also arranged visits to the new after-school club, not that he may be using it next academic year.

We don't celebrate new year, but have done Jesus' Birthday. DS likes singing Happy Birthday and so we get that a lot between Christmas and New Year. So Jesus is 2014 years old and Liebling thinks that is hilarious because it's so old.

When he tells me about things people say/do at school we talk about his responses and what outcomes he would like. And sometimes it is just telling the teacher that people are upsetting him when they won't stop saying things that don't fit his reality.

So yes, I would say normal and this is how I work his normality into our lives.

Snowy Love, tried to PM you but your inbox is full. :)

Cleared now!

I try to let him know what's coming - we talked about DH's car for two weeks before it came & it was two weeks of upset.

Have you asked him why these things make him sad? And I don't mean a straight one word answer but a full conversation? Is it possible it's transference? Is there anything else that could be bothering him but he is unable to fully vocalise?

I only say this because I was very guilty of this as a child. I would burst into tears over something that seemed trivial to everyone else but it was usually compounded by a bad day, something that had played on my mind that I couldn't say or tiredness. My daughter is like this. And it's taken us a while to work backwards so she can see it too. And she is 12. She told me once she cries on the inside but sometimes it falls out. That sounds way more awful than it is. But we've been able to work on it. I don't think she is suffering. But she is very empathetic. She used to worry about being upset about things and telling us in case they upset us too. Apparently that's common for kids who have a high EQ. It's still a work in progress.

My DS is the opposite, very dramatic and very open with how he feels. Not a bottler, and when he does bottle it manifests physically almost immediately.

Sorry for rambling, it's just something we've worked on for a long time and this is exactly how it produced itself, although a little younger for us.