Why do I do this?

Message people from the past. An ex for example. This is a habit. I'll go months (in fact it has been almost a year) without saying a word to her then suddenly I feel a need to message her and see how she is doing. Nothing mean happened yet this time but I feel that it is not really the best choice since it's unpredictable. I get nervous and I feel like I want to talk more and more. I do not have much evidence, but she probably does not feel that way. I can see that because it is very one sided. I ask a question and she answers. That is really it. And she just stops responding completely a lot (which thankfully does not bother me as much as it once did).

I get other urges to get in contact with other people from my past as well. An example is a couple of old good friends who broke off a friendship when I was still friends with one of their ex's. Quite immature. They have not talked to me since but I really miss them. I don't know if I should try to reach out or not.
I even wonder how some people from High School are doing (that is 4 years ago).

Why do I do this? I cannot figure it out. And I don't know if it is bad or if I should accept it. My mother is extremely unsupportive of it and at a loss as well. She says "I don't know why you do these things!" Well, truth be told I do not really know either. "You open yourself up to nasty remarks", she says. And that could be true. I do not handle rejection well at all. But it is like some part of me wants to have a connection with people from my past. It's like I cannot fully let go...that I just want things to be the same again. It's like nostalgic feelings I guess. But why do I feel such a nerd to reach out to all those people?

Does anyone relate to this or have opinions/advice? I don't know if I should stop doing this (probably) but I do know that letting go is probably important and I'm not good at that. Help/speculations on why I do this?

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Rejection and abandonment seem to be a common theme.

I dont know if you care, but my close friend does EXACTLY the same thing. She messages Ex's that didnt end well, and then wonders why they "abuse" her. She always wants to contact people from years ago whos relationship with her didnt end well because "its sad to lose that connection" and she needs constant reminding that she is popular or has people who will reply to her desperate texts. She is working on it in therapy for BPD. Shes not yet ready to do DBT at this stage, she has a lot to learn about herself, although now she is aware of her behaviour, which it sounds like you are too.

Are you in therapy? I cannot relate to messaging ex partners but I do think it is normal to wonder about those in highschool. I loved my high school reunion for that reason.

Without knowing the specifics, I can't judge whether I think you should cut ties or not. Only you can really judge that. (Sorry about the cliche but it really is true) It could go either way for me. I've cut ties with most people from my past but I do still get nostalgic & some I miss more than others.

I'm still friends with some of them from my past. I have a small circle of people I still consider close friends/family. Others are just acquaintances through FB & it's a "hi, how are you? How's your family?" kind of thing then we don't "talk" again for months or sometimes years.

I don't know if it's age related or what but I've drifted apart from most of the people from my past I used to call friends, but some of them used to be very close and my MIs destroyed those friendships. To be truthful, I also think that if they were truly as close of friends as they once claimed to be, they wouldn't have left me behind when the going got rough. My true friends/family stuck around & I've been there for them.

I've learned through the years to just let go of certain people. I cut them off like they did me. Maybe that's not always healthy but it rids my life of some of the pain once I get over them. That way I can move on with my life. That's also why I love my pets more than most people I know and those closest to me know that.

I do this when I'm manic, pretty much every time. I reach out and try to reconnect with people from my past, as well as try to connect with new people. When I'm manic - before it get bad - I'm super social and outgoing and fun to be around so I like to connect with people to go out and do things. But that's just not me. Typically, I'm more of a loner that doesn't have too many friends or people that I associate with. I generally enjoy doing things on my own so connecting and trying to reconnect with people is definitely out of the ordinary for me even though I'm surprisingly not on bad terms with most of the people from my past except maybe two or three people.
Like you said, you probably do it because of some nostalgia factor and because you have trouble letting go. If you are opening yourself up to get cut down, you probably should just let things go. Tell them "Hey, I'll be here if you want to talk or get together." to put the ball in their court. That way you know if they respond, they want you to be in their lives and if they don't respond, then you know they don't want to be friends with you. Talk to your counselor or therapist about it. And instead of trying to reconnect with people from your past, why not find something you could to to create friendships with new people?