I [20F] am becoming a jealous monster by my SO's actions [24M]. Does he need boundaries or am I crazy?

It feels really glad to have you explain things a bit from how I'm feeling it but in a less emotionally charged way. I appreciate you seeing this from my perspective. I truly don't know how to handle the photo thing, the one time I brought it up it seemed just crazy to relax. But how can I happily post about us on social media? I'm embarrassed to show family members and such because it's like >2+ years of really HQ photos of him/ex on dates and cute couple-y, a few random photos, android grainy bad selfie of us, photo of him/friends (including a hugging pic of him/city girl SOLO from a few months ago), another modest few couple photos, then 6 couple like photos of him and aforementioned citygal, and finally some more photos of us. As soon as I uploaded them, his friends tagged him in "memory" posts which were actually far-away beach photos of him (including ex.)

It just feels really awkward for me. I don't want to show it to my family as I can't explain it. My friends think it's weird and scroll and are like who is that. I rarely want to look at his social media because it's everywhere and just gross seeing these pics of him with his (very attractive european fit gorgeous beachbody ex) and it's awkward uploading photos of us because only my friends seem to "like" them (he has hundreds of FB friends) and then it's always overtopped with a ton of nostalgic posts or him with other people/

God it sounds so petty when I write it out but he's like the only person I know in the whole country and given that my schooling is online, most of my friends are online, I'm fairly introverted, have moved a lot, etc. social media is a heavier part of my life as if I didn't have it, I'd have no realistic connections with old friends.

The uncomfortableness was acknowledged but he seemed a bit upset that I was upset but did tell me I had nothing to worry about with his ex and that I am beautiful and then he took me to a nice dinner to forget about it. So that was nice. I just feel like I'm in a situation with his childhood friends where I can't win as his ex has won them all over (and continues to do so.)

The meetup was unexpected for both of us (he claims she texted him.) all I know is I was texting him good morning, told him I had to wait 4 hours (the strangers literally took that long to get me) and kept trying to initiate conversations. He just would reply a bit short but sweetly and I sent him a few texts that he didn't respond to so I just waited thinking he was at work. I'm texted hours later out of the blue to like a huge wall of text about her and how her ex was awful and poor her and how her nursing is going well. I have never met her in my life and had no clue he was out with her. He didn't text before or after that or indicate at any time about the plans until after.

The cheating was when he was older, I fudged the ages/dates a bit as my SO is a literal compsci major and I'm not very good with computers and would prefer that this isn't something he reads because I don't want him to feel bad about it and this is private for me.

When should I communicate these feelings? I feel like if I randomly mention it, he will feel like I am just trying to start a fight. We discussed the citygal issue for like a few days in a row and it led to him being a lot softer and comforting me but only after I fully apologized, gave makeup blowjobs, etc. I feel like he only did that after I conceded, if that makes sense.

The last paragraph is great advice. Should I keep it in mind and mention this stuff if we have another argument or should I bring it up before hand to prepare? Additionally I'm getting conflicting advice that I'm jealous as well so I'd like to incorporate that so I'm not pointing the finger of hypocrisy without realistically knowing how to improve upon my actions and be a better GF.

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