I’m (41m) trying to figure out when and how to introduce my girlfriend of ~1 year to my parents, siblings and their kids, and my daughter (17). I’m hopeful to marry girlfriend someday, catch is it would be my 3rd marriage.

First marriage lasted 9 years. Had daughter. Awful divorce. Honestly awful woman I never should have married let alone had a kid with. Married too young, I was only 22. She was considerably older and I was confused or just dumb. Plus she might’ve even been low key predatory (started dating her when I was 18, she was 27). Family liked her well enough, accepted her for my sake.

Second marriage lasted 3 years and was a really sad but not bitter or hostile divorce. No kids. Part of the reason we divorced. Won’t get into all of it but I still feel love for and consider her to have been a great partner and beautiful person. I couldn’t really be pressed to say a bad thing about her. Still the divorce was my doing, I wanted it first and ultimately was the one at the wheel. It’s been 2.5 years, and my family still laments the loss of her in my life and their own. Not openly exactly, but it’s obvious. They really loved her. Thought she was great for me, saw she was great for me. Though that was probably influenced against seeing how terrible my first wife was for me. But they never didn’t support me in the divorce, so much so none of them tried to keep their relationship with her outside of me. I know my sisters have regrets or feel painful about that, and I think my mom does too.

That all said, I’ve been reluctant to bring my current girlfriend into their lives. I just feel conflicted. Like they’ll be bracing themselves. Putting on their game face, like here we go. But not genuinely care. Or maybe even be barred from liking her because of how much they loved my ex. I don’t give a shit if they judge me, I just don’t want their internalization of her to suffer. I don’t want them to judge her. I’m not sure if I have any tools to negotiate this for best outcome, if time is my best ally and to give my family more. But whenever I consider that, I just think it’s going to cause me to grow further apart from my family. I’ve been avoiding them almost involuntarily because I want to spend most of my time with my girlfriend. And I’m fearful to include her in time with my family. So I’ve just been choosing her.

Not too worried about introducing her to daughter. As you can imagine daughter didn’t totally accept or like my ex to the degree my family did, so I think she’s the only one that I actually don’t have to worry about writing off girlfriend out the gate. She actually already knows her and likes her, hasn’t been around her in years though. She just doesn’t know her as my girlfriend. (We’ve been very casual friends for 15 years. I had a little crush on her when I first met her and I was realizing how much my first wife was a nightmare. But no serious legitimate feelings until we reconnected last year. I hadn’t actually seen her in several years until then.)

Anyway sorry this is long. Hoping for any insight or advice.

TLDR: afraid to cause my girlfriend and/or my family pain or struggle by introducing them to each other too soon, if my family doesn’t accept her right away due to them having unquestioningly accepted both my ex wives and now feeling jilted because they loved deeply my 2nd wife and miss her.