Does Anyone Have a 5 Year Old That Still Cries a Lot?

If he's making friends at school then I wouldn't worry so much.
I think a little social anxiety for this age can be pretty typical.
I've know one boy who was 7 yrs old before he really got over it and then it was full speed ahead!
He's a well adjusted outgoing teen now and you'd never know he use to cry over everything if you saw him now.

Hey K.,
Crying is an attempt to communicate something, but it generally causes more stress and confusion than clarity. Part of our job is to help our children develop their communication skills. That being said, here are a few things that I have found to be very helpful in this area and hopefully you will too!
So to start with security: kids are vulnerable and they are quite aware of it, not to mention always being reminded of it. (Be careful, stay close, don’t talk to strangers etc.) While it is important for them to be aware of safety, I have found that children, especially ones who are a little more anxious benefit when we give them empowering directions. So instead of “be careful” try: “You climbed so high on those monkey bars, you’re pretty brave! If you start to get nervous coming down all you need to do is ask and I will help you.” This is so much better than the hanging “be careful” which directly implies that they are in some kind of danger, and that we are nervous for them. Instead, it’s better to acknowledge that they managed to climb up, but that there is some danger when heights are involved, and if they need help, all they have to do is ask, and we will help them. By letting them now that they can ask for help we empower them to do something about it, and give them a sense of security in that we are there for them.
Now my second tip is: establishing clear expectations and setting game plans ahead of time. This one is SOOOO beneficial for anxious kids. Helping them know exactly what to expect and then providing them with a game plan for how to handle things they are uncomfortable with is, again, very empowering for them. So for instance if you are invited to a birthday party, first tell your son and ask him if he would like to go. If he says yes, begin explain to him everything that will happen. Be very clear with him, to the best of your ability, about all of the fun reasons to go, but more importantly all the things he may be uncomfortable with. So: Jack’s mom asked if you would like to come to his birthday party this weekend. They are going to have a bounce house, cake, all the kids from your class, and some of his friends from his karate class will be going too. They will be playing games for prizes and Jack will open presents. There’s going to be a lot going on and I am sure you will have lots of fun, but you don’t know the kids from Jack’s karate class, and I know that sometimes strangers make you uncomfortable. So if you do start to feel uncomfortable just come get me, and I will help you to introduce yourself to the other kids. Jack really likes them so I am sure you will like them too!
Tip number three, modeling and helping him to engage in proper communication. Now modeling proper communication is pretty obvious (I’m sure you do), but the real point is helping him to engage in proper communication. So whenever an instance arises where he begins to cry, give him real feedback and positive direction. So say you get to the party, and he gets nervous and begins to cry. When he does give him a hug, help to try and make him feel more secure, and say: “O honey, did you get nervous because that boy who you didn’t know began speaking to you? It’s ok to feel nervous, I get nervous sometimes too, but you don’t need to cry. Instead you can come get me and we can go sit in the car and talk for a minute until you don’t feel so nervous.”
Now, I know a lot of people out there believe that you should just let him cry, or not discourage crying, and that he will grow out of it. The problem I have with this is that generally yes they do “grow out of it” but generally it is because they get poor reactions from people around them for crying, because crying in those instances at that age is immature. So instead of learning and growing out of it with you by his side, because you gave him honest and loving feedback, and he now has the tools to face and handle situations that are uncomfortable to him, he will “grow out of it” because he got dirty looks and made fun of, which will only lead to other problems and issues.
It sounds like your son is kind of sensitive and a bit of an introvert, both of those are great qualities, but communicating with sensitive introverts can take a bit more work sometimes. As his parent you are in the best position to find what works for him, and it’s awesome to see a parent getting out there and looking for the answers to meet their child where they are at. So kudos to you mama, and good luck!

Love, love, love JC' s idea of letting him speak for himself!! And then praise him for it! It will build his confidence so much! I was fearful of doing this kind of thing as a child, so I encouraged my son to speak up for himself at every opportunity and he grew to love doing it. You can practice with him at home. Play store and you each take turns being the shopper and clerk. Play restaurant and you each take turns taking the food order. Play birthday party and role play having a great time with friends. He will have all this role playing experience in his tool belt when he needs it.

This is totally typical for some children. The difference at school is that it is structured and has a routine. Knowing that he is more comfortable with smaller groups, that's how he will develop his skills. I'd suggest he have opportunities to do things with friends at your house or at the playground to continue to build his confidence. And I imagine it can be embarrassing, but please channel those feelings into helping him out when he's overwhelmed. He will love you always for your understanding. My best to you and your son.

My son would sometimes fall or get hurt, get embarrassed, and then cry his little heart out. Only I was allowed to hold him-- no one could even LOOK at him.

And don't you know, he grew out of that at some point. Sometimes, being a kid is just HARD.

But I want to ask this question: why is it frustrating and embarrassing for you? You aren't the one crying. You are going to have to learn to release your sense of control about this. My nephew used to cry at the drop of a hat and I'd cringe when I heard my stepmom comment "he's such a wimp". Kids have a lot going on inside them, just as adults do. I understand that you want him to be easygoing and fit in with peers (don't we all) but some kids are going to take a while before they get to that place. I love the book "How To Talk So Kids Will Listen... and How to Listen So Kids Will Talk" by Faber and Mazlish. Learning to let him have his own feelings while staying receptive will help. When mine would get upset at a young age, I'd just take him to the side gently, "we need a little break, I think" would be my only real statement about it. And like I said, at some point, he started being able to brush things off more easily. Time, maturity and such will help. And accepting our kids as they are, in this moment, helps too.

Mine just turned 7 and did have a similar phase than your boy. Just don't give him the feeling it is wrong what he does. That will only make it worse and takes longer. Give him reassurance that all is Ok and he can hang out with you as long he needs to warm up with the situation.

It is really important that you don't push him. He needs that security with you!

Be a little patience with him. Mine lost his insecurity in 2nd grade and still has the moments to hang out with me which I actually keep as a treasure. They will get so independent soon.

Stress. Our son wouldn't cry, but if it was an unfamiliar situation, he would just demand to leave or practically meld his body into mind. What I found helped was not to "push", if he wanted to cling to me, I didn't make an issue or it, and I would just put my arm around him. Sometimes he would venture out, other times, he would hold back, but he seemed to make more progress if I didn't make an issue out of it.

Where he does warm up to kids after a while, I think it's ok. I have one that had some social anxiety. Older in fact. She outgrew it in the end. I was bothered by it far more than anyone else, so I had to learn it was just my kid and it was ok.
What helped us was having her take on new challenges - riding a bike, etc. and building her confidence really helped. Mine would be fine one week being dropped off to an activity but not necessarily the next. I think you'll find that there are quite a few kids like this. Every kid has their own thing - he will likely outgrow it. If he's making pals and does become comfortable once he's adjusted, I'm sure he's fine. Just don't make a big deal about it. My kid was always better with her dad. She sensed that I was a bit bothered by it, and it stressed her out a little, which didn't help.

My girls were on the quiet side. When they were 5 I enrolled them in a drama class (Drama Kids). I think it really helped both of them come out of their shell. My oldest was nominated "Miss Congeniality" by her class mates four years in a row in HS.

I also gave my girls every opportunity to speak for themselves. They had to announce themselves at the doctor and dentist office, they ordered for themselves at restaurants, I had them answer the phone. If they were looking for a toy or book they had to ask the salesperson for help, they would pay for our order at the convenience store etc.

Many 5 year olds tear up or cry pretty regularly. Some are more emotional than others. They eventually outgrow it, most by age 8. (Although a few years later, you're into preteen hormones so...)

The issue here is that you're embarrassed by something normal. You need to figure out why it's bothering you, so you can put it aside. It is important that you're not scolding/shaming him for having a legitimate emotional response. Deal with misbehavior tantrums, of course, but handle the issue rather than the tears.

He probably has a shy and sensitive personality. Help him to be more confident in himself...make this a long term goal. Encourage him to stay his feelings instead of crying. Teach him to state what he feels and what he wants. Praise him for this. Help him to learn how to properly put his thoughts into words. How to stand up for himself. How to be strong in his own convictions. Teach him how to talk to other kids. Practice with him at home before you go to the playground. Role play with stuffed animals if he seems stuck. Encourage him to be brave, to introduce himself, to state his opinions, to talk about his day. Ask him his thoughts on things at the dinner table. Praise him and build him up. Let him debate you when he is older and praise his critical thinking. Encourage him to set boundaries with other kids and not let them walk all over him. Build up his confidence in the things he is good at. I was a shy and sensitive kid. I lived with a narcissistic mother who never once thought about these kinds of things. I was expected to listen to her, do things for her, be quiet at dinner, told I was too sensitive, and my feelings were never validated. Your child is only in Kindergarten....you have many years to work on these things with him and to help him grow to be an amazing person. Have patience and start today!

Completely normal. Some kids cry to release stress. If he doesn't cry then he will have stress built up and built up. Then explode.

Let him cry. He'll grow out of it.

Oh yes....I have a 13 year old dd who cries quite a bit - has always been quite a crier. Very sensitive...and the hormones haven't even kicked in yet.
Some kids are just sensitive souls...it will probably be this way the rest of their life.