How should we navigate this friendship kindly, but not be suffocated?

I'm likely not a nice person, but I would request that my son not be in the same class as Leo.  A second grader is not mature enough to handle the pressure of another kid who is constantly depended on him for entertainment and uses emotional manipulation (which I view to include asking if he is still his friend the moment he plays with other boys, even if unintentional).  If Leo needs more emotion support than the teachers can provide it or the kids can play together in recess, but it should not be the job of a second grader to serve that role.  If your son does end up in the same class as Leo, I would make sure that you son is not isolated from other friends either by asking for teacher's help in that (your son gets at least 1-2 recess a week where he plays with other friends) or at least by scheduling regular playdates with other kids in his class.  Leo needs support and is beyond nice of you to allow your son to serve in that role, but as a second grader he is still a kid and in my view it is your job as a mother to make sure that serving in that role does not come at a cost of his own emotional well being and friendships with other kids.  

P.S. I likely feel stronger about this than most since I was in a similar position to Adam and Eddie in elementary with a friend who attached herself to me (like Leo in your question), and I'm beyond grateful to my parents for extracting me from that situation (they moved me to another class/recess period mid-year) and allowing me the freedom to play with many other kids and not have another child following me around and crying every time I wanted to play with someone else or do something else and making me feel guilty and like a "bad-friend" for even expressing an interest to play with other kids.  At the time I thought it was fine and that she just really liked playing with me but looking back as an adult I see that relationship was not healthy and my emotional and social well being in school improved drastically after I was separated from that friend. 

I feel for you and for all of the kids involved. As a child, I often asked my best friend in elementary school if we were still best friends at random times, usually when I was feeling particularly insecure. I was a worrier and my insecurities got the best of me at times. I agree it wasn't my best friend's responsibility to provide me with emotional support and stability, and she often told me that she wouldn't be my best friend if I kept asking. That was usually enough to keep me at bay for a while. Eventually, I did grow out of this and she and I were very good friends until she was held back and we were no longer in the same grade. I say all of this, not to suggest that you just wait it out, but to share that I can relate somewhat. Has your son ever let "Leo" know that he doesn't want to play with him when he acts certain ways? That seemed to work in my case though the message needed to be delivered more than once. Perhaps there are things going on at home for "Leo" that are influencing his singular attachments? Lot's of possibilities, but at the end of the day, I totally agree that your son deserves an environment that is freeing and joyful. Hopefully the summer break will help. Lots can change in a few months. 

Your post resonated with me. I can empathize as you try to deal with this difficult situation in a compassionate way. Parenting is hard. 

My kid (call them G) had (has?) a friend relationship like that. They met in middle school, so they were a bit older than the "Leo/Adam" dyad, but the dynamics were very similar. G's friend (call them H) just had a lot of emotional immaturity. H wanted to hang out with G all the time, and got jealous when G spent time with anyone else. It was hard for G to learn how to navigate boundaries with H, and we had a lot of talks about G's responsibility to their on personal space, as well as being kind to H. At the time, G was seeing a counselor (for other issues) who helped G sort through their feelings. After they entered high school, H felt abandoned by G as they developed new relationships, and there were hard feelings. Right now they seem to have worked it out, although they have mostly drifted apart. 

I think it's common for kids to attach themselves to people who will enable them. In my kid's case, this has come up a few times but not so extreme as it was in middle school. My kid ended up playing the role of "counselor/therapist" for their friends and it compounded the problem. It was very helpful for my kid to have someone else to talk to about what was going on, and to recognize patterns in their own behavior so they can make good decisions about their relationships.  Group therapy, or social skills classes, would benefit your kid as well "Leo," for different reasons. These are great lessons to learn about co-dependency, interdependency, setting boundaries, and compassion and kindness. Since the kids in your case are young, obviously these terms are a little out of their developmental understanding, but they can certainly start to work on the same concepts. If you have a trusted and knowledgeable teacher or administrator you can ask for advice, please do so. I'm sure they've seen this sort of stuff a lot. Best of luck!

I agree with the other reply. I absolutely would ensure that my kid wouldn’t be in the same class as the emotional vampire child. Sorry but your kids needs come 1st.

- Jamie 

I would discuss this with my pediatrician or family therapist and ask for a written letter with their recommendation for your son's class placement.  This is too much pressure for a young child to deal with these intense needs.  Your son can be a supportive friend to Leo on the playground, but having to be in the same class given the past dynamic with him sounds inappropriate and unfair.  A letter from a professional will be considered seriously.  If you are unsatisfied with the placement decision, you might ask for a Student Study Team meeting (in writing) to discuss your concerns.