My boyfriend of six months used to date this girl for 4-5 years in high school/college. I'm his first official girlfriend since her, as the rest of the girls he's dated have sort of been plates (no label) or flings. They broke up about three years ago, but he remained very good friends with her and her family, and actually stopped hanging out with her as much about two years ago (but he still hangs out with her siblings from time to time and talks to them often).

He initiated the breakup, and it took about a year for them to be officially broken up, as they kept getting back together and breaking up. He has confided in me that she was very depressed the last year they were together, and remained depressed after their more "official" breakup and he checks in on her from time to time. He has been very honest about the whole thing and tells me when they text, he says his endgoal is to always make sure she's not suicidal and doing ok, and try to wean her on a support group that doesn't involve him. She also has a boyfriend.

So initially, I was never threatened, especially during the early stages of our relationship and especially after he explained that she was depressed, and being the newer gf, I didn't want to step on any toes. Lately, though, I've been more bothered by some of their exchanges. They only text once every couple of months or so to catch up, but they snapchat a lot and he snapchats his sister a lot, too. They will message on snapchat small things about whatever picture they sent like "oh that sucks!" or "oh that looks fun!" or whatever.

Bothersome incidents

Over the summer, he showed me their text exchange (because he is very open and shows me), and I saw that one of their conversations started by him sending her a youtube link to this love song that he also showed me around the same time he sent that to her. ("Hey watch this!---") That really pissed me off because he said he never hits her up and it's usually her. It also just made me feel not so special since he sent her the same song he shared with me. I ended up not saying anything because I didn't want to make a big thing about nothing, but earlier this month he was humming the song and it reminded me of that and he asked me what was wrong and I told him and then I ended up feeling stupid for bringing it up. He said that he didn't mean anything by it and understood, but also said he didn't consider us very serious when he sent that, which also bothered me.

Recently, he told me she hit him up after this surgery he had, and that it was a short conversation. However, later when he drunkenly showed me the exchange, I saw that it was sort of a long winded conversation and in it she said she missed him and that she'd been dreaming about him. He responded with a simple "I miss you too" and then she sent him a few more texts about some app and he stopped responding. When I confronted him, he just said "I don't know why she's dreaming about me she's crazy" and when I talked to him about how it made me feel weird he emphasized that he was just making sure she had a support group. He was kind of drunk when we were talking about it so I'm not sure if he even remembers that I was bothered.

The other incident that bothered me is that a picture of her and her bf showed up in his fb feed and he asked me if I thought he was more attractive than him.

Other little things are that he's always sending snapchats to his sister (who has a bf) and her, and he will make sure there is no trace of me in the chat, just the fun thing of whatever we're doing.

TL;DR My boyfriend stays in contact with his depressed ex-girlfriend (4-5 year relationship, broke up ~2 years ago) and her family (in a non-depressed context) and tells me it's because he wants to make sure she's doing ok and has a support group. Their most recent conversations do not talk about her meds/condition or anything, and are just light catching up. I admire that he wants to help someone out and I don't want to belittle depression, but some of the incidents described above really bother me. He tells me he feels partly responsible for her condition since he initiated their breakup, and feels her life is sometimes on the line. I don't get that impression from her bubbly snaps and catchups with him, but of course I don't know the situation and someone who is depressed will hide it well. Am I overreacting? If not, how do I bring it up to him without sounding insensitive/jealous? Next time he snaps her, I'm thinking about saying "look I understand you're trying to make sure she's not going to kill herself but I draw the line at love songs and "dreaming about you" texts...does that work? Should I be bothered by snapchat?? I also understand that he can't really control what she says to him, only what he says back. I guess I also feel that sometimes he's just using the "she's depressed" card as a quick excuse for talking to her.

EDIT: Here is a bullet form in case that is easier

So the things that I appreciate:

  • He is open about his contact with her, and always tells me when she hits him up or texts him. He doesn't tell me about every single snapchat, but I think that's juts because that would get annoying and excessive.
  • He said that if she ever implied she wanted to still be with him, he would shut her down,
  • He said he would never meet up with her.
  • He tells me his endgoal is to get her on a support group with her friends that don't involve him.
  • The times that they talk substantially (not just a quick snap) are a few months apart and usually by text. He says that one day in the future she might give him a call to catch up but that hasn't happened in a while.

So the things that bother me:

  • He is still really good friends with her siblings.
  • They send snapchats to each other and often will reply with something short like "that looks fun!" or whatever
  • I don't think she knows he has a girlfriend, though she might know he's seeing someone
  • When they used to talk, I could tell the end of the conversation would be my boyfriend asking her about her meds, etc., but the last couple of times have just been small talk and not about her depression
  • He sent her the same love song he sent me on youtube (is it childish of me to bring that up?)
  • She said that she misses him and that she's been dreaming about him. He responded with a simple "I miss you too" but I wish he had said something else (like "wow must have been some crazy dreams what else is new?")
  • The few times I've brought it up he's assured me it's nothing, but the conversation always ends on "well she's depressed and I feel obligated to support her and I'd be a horrible person if I didn't"

I don't think he'd cheat on her with me, but sometimes I worry he still bonds with her. If the roles were reversed, he'd be really upset with me, but I know men and women are different with jealously. I would never help out an ex like this, but I am a female with male exes.

EDIT: I should also mention (I just remembered) that he was on narcotics from surgery when he said the "I miss you too" bit but that still bothers me