my second grader cries almost every other day, sometimes daily, sometimes more than once a day. Whether pain, frustration, or sadness, hmm, is this normal?

Part of me says he's a boy, and boys should act a certain way. (ie, boys don't cry)

Part of me says, oh, he's still my baby! And I just want to hug him forever.

I'd check with school and see what they are observing...bully/fear of subject/overwhelming load/etc/big non-school life changes....crying like that is not usually typical boy or girl...it is almost always pitted/rooted in something deeper....get to the root of the problem to help it...good luck!

second grade...that's age 7ish, right? (I can't ever keep grades straight LOL)
Yeah, check into school other social things, see if anything is going on.
But, could just be an emotional time. We readily think of girls getting all emotional as they approach puberty...which these emotional roller coasters can actually start at 9 or so..but we forget boys have the same things gong on. They get emotional too.
It happens around the same age for each, but as with everything else, each child is different and some may experience it earlier than others.

I'm a 'be a man' kind of boy mom myself, but at the same time, understand this and try to accomodate. I am trying to teach them to talk. And I know sometimes you just don't know what to say..as the one who is emotional..you don't know how to describe what's going on, what you're feeling or why. You just don't know. I am still that way, at 33 LOL So I know my boys come by that part naturally. But nonetheless, I try to get them to talk...just *talk*. If something's wrong, tell us. Even if you don't really know *what* just let us know you're feeling 'off'. Maybe we can help talk you through it. Assure you things are ok. Help them to see/think rationally. Let them know they are not alone :)

And remind them that they have control over their feelings. It may not seem like it at times, but they still do and they are responsible for them. They can't just shut down and act like utter fools. If they need some time to themselves, fine, retreat to your room to do so. If someone comes to 'bother' you, just explain you would like to be alone for a bit. We will all respect that, allowing you to regroup. But after a while we expect you TO regroup and come back out with the rest of us.
There does come a time when you must 'buck up and be a man'.

Hub helps greatly with this. See, we're rather 'reversed'. He's the outgoing, emotional, talker. I'm the 'shut up, get out of my face, leave me alone' recluse. He gets upset or sees a problem, he wants to talk it out. I just want to be left alone...I'll 'get over it' then go on with life. But he cannot stand for me to 'walk away'. He wants to talk and resolve it.

So, having that in my husband..I know there can be a balance of allowing a boy to cry and be emotional as well as 'be a man' KWIM?

I'd say encourage him to talk...don't coddle. Encourage him to discover the reason. Encourage him to get control of himself. Let him know you are there to talk to. You ARE there for him. I just wouldn't give into the 'aww my poor baby' thing, myself. But I'm not an 'aww my poor baby' kind of mom in the first place. Kid falls and busts his lip "oops....oh well, you'll live...go on, goodbye.." ;)

Gabe cries over silly things all the time. it may be an age thing, I dunno

He could be an HSP: http://www.hsperson.com/index.html ?
It's not a bad thing. I haven't read the book yet.

my daughter is 7 too and she cries over things that we think aren't really things to cry over, and when we sort of expect her to fall apart about something she is o.k.
we just encourage our kids to talk about what they are feeling.

jake ( 4 years old)still cries when i drop him off at school, and i remind him that it is ok to be sad and miss mommy but that we need to use our words. it seems to be helping ( he has gone to school for 6 days now and no tears)

I'd check with school and see what they are observing...bully/fear of subject/overwhelming load/etc/big non-school life changes....crying like that is not usually typical boy or girl...it is almost always pitted/rooted in something deeper....get to the root of the problem to help it...good luck!

I know right where it's pitted... with his brother. Willie tries everybody's nerves, and it's no secret Aiden wishes that "Willie wasn't special needs". But he is.

I guess I'm trying to get a baseline and see if this type of thing is normal for his age, or if I should seek medical/professional help.

Does he get special time with you every day? He may just need some extra attention and may be trying to get it by crying. If you can maybe you could set aside a time, before bed, after supper, etc., that he can count on having your full attention, it may cut down on the crying and let him know he is really important to you.