Can I (34M demisexual) have a happy marriage with a close friend (34F) into hook up culture or are we fundamentally incompatible?

Our friendship:

“Jill” and I met freshman year of college. We shared similar hobbies, goals, sense of humor, etc. We immediately hit it off but as we were both already dating other people so I didn’t imagine anything more. Over the years we grew much closer, sharing just about everything with each other, going on trips with each other, staying the night at each others place, etc. but at no point did our friendship become anything physical beyond hugs or leaning on each other. No sex, kissing, touching, etc. I was in a long term relationship for most of the 14 years I’ve known her and she’s basically never been single for more than a week or two. I’ll admit I crushed on her a couple times but given one of us was always in a relationship with someone else I’d just retreat from the friendship for a few months until I got over it.

Recent friendship:

A couple years ago things sort of changed. We share friends and often would say goodbye with “love you all, see you soon” or something similar. She started saying this sort of thing when it was just us. She gently hinted at us sleeping together. She suggested I would make a good father. She mentioned wanting to have kids but not being able to find a guy willing to commit. None of this was stated clearly, just all vague brief interactions like “What do you think about friends sleeping together? It’s not a big deal right?” A couple of our shared friends suggested she has a crush on me which makes sense but our relationship dynamic has been sort of weird for nearly two years now and crushes don’t really last that long.

My problem:

Alcoholic single mom and a string of terrible “father” figures in and out of the house as a kid. I’d listen to my mom cry herself to sleep every night for years. At a very young age I resolved I’d never be like these irresponsible men that were coming in and out our lives. I set all sorts of sort of semi-harmful standards for myself like “Value others for what you can give to them, not what you can take from them.” It took me most of my adult life to learn that I need to be sort of selfish if I want to have some degree of happiness and self-sufficiency. When it came to dating I had this idea that I only had a positive effect on the women I was close to. This resulted in me avoiding any sort of interactions with women if I thought there might be a small chance of her experiencing regret, discomfort, unhappiness, etc as a result. If a woman hit on me a party and I thought she might be drunk, I’d make sure she had friends there and a way to get home. If I crushed on friend I’d keep it to myself instead of risking making her uncomfortable by admitting it. If a friend hit on me I’d play stupid unless I was 100% certain of her intentions. I basically always just took the “safest” options. A consequence of this was clinging to the few relationships I did have despite them not working. I’d forgive girlfriends for cheating, tolerate being hit or yelled at, etc. I don’t have a very happy romantic history.

My problem as it relates to Jill:

Jill is basically the exact opposite of me when it comes to dating. She was into female seduction authors or stories for years. She’s the only woman I know that likes unsolicited dick pics (so long as the guy has nice abs.) Her attitude has always been something like “men are awful, attitudes around sex are male dominated and enforced with violence, women are the mothers of humanity and the feelings of men should have zero bearing on her sexuality.” I share a lot of that anger towards men so we sort of agree on some of this but she takes it to an extreme where she will hurt people in a pre-meditated way because they are men. She has had a long sex bucket list and mostly she’s used dating apps and “fuck boys” to check things off. This never bothered me because it seems like both parties understand they are using each other and are fine with that. The problem is she’d also seek out naive, inexperienced, gentle dorks to keep on the side for emotional support. She’s justified cheating on these guys with “it’s only sex.” Eventually I started feeling really shitty when she would introduce me to her newest guy because I knew he’d be heartbroken in a couple months. I told her she needs to be up front with these guys and let them know what to expect because they are being genuinely hurt. Surprisingly she took my advice and started telling guys her views on men and to not expect anything serious.

Maybe my other problem:

I have a couple friends in the polyamory community. They sleep around a lot and I don’t think any less of them. I think it’s because they’ve put years of effort into learning open and honest communication, setting boundaries clearly, developing emotional intelligence, etc. From talking with them I never got the impression they see their partners as “less” than them but instead it seems like they try to create a happy outcome for everyone in their poly circle which seems way healthier than most monogamous relationships. Jill’s history does bother me. It feels like she’s demonstrated calculated coldness towards others and used her looks and sex to take what she wants without regards to the consequences or the feelings of others. I cannot separate sex from the emotional side of things her actions here don’t make sense to me.

Current situation with me:

Jill asked me “why don’t we get married?” and another friend confirmed she’s been into me for years. I genuinely love her, we have amazing times together, we know everything about each other, we both have been attracted to each other physically, we would likely make great parents, etc. So much of everything is perfect but I can’t get past her past treatment of men. For months now I’ll catch myself daydreaming about some future we have together and feel enveloped in happiness… then I start remembering the long list of things she has said and done that are not compatible with love or a stable family life. I’ll become fatalistic and think “well she’d just be using me like she’s used other men” or “she’ll just cheat like she did with other men” and then the happiness fades. Then I start thinking “I sacrificed happiness in order to make sure I didn’t hurt women. She’s hurt so many men, why does she deserve happiness with me?” I think this thinking is tied to anger I still feel towards the men that were abusive towards my mother. Is this just my problem or does she have a real problem?

Current situation with her:

She says she’s no longer able to have hook ups, she’s tried a bunch of times over the last year and never made it past kissing. She went back to a guy she had dumped because I guess she can be physical with him and not feel sick like with other guys. She complains about him and says she doesn’t have a future with him. She wants to have kids soon and feels the time pressure. She still has feelings for me.

Summary:

I reread this and I worry I’ve portrayed Jill in an unfairly negative light. I am a fairly social person and have healthy, close friendships but of all of them Jill is maybe the most generous, thoughtful and kind friend. Jill has never done anything even remotely negative towards me. Jill has never used me for anything; she has money, a career, a wide social circle, close friendships, etc. We’ve known each other a long time and I’ve been awkward, rude, or careless at times. She’s never reacted to my worst with anything but patience and warmth. We both love each other and could potentially make each other happy for the rest of our lives but her history and attitudes toward men make me think I might be falling under the same spell as the other guys. I worry that her past is the result of some immutable character trait and 7 years from now I’ll be changing diapers while she is on a cruise with her new fling. Or maybe I’m just projecting the unreasonable and harmful expectations I’ve held myself to onto her and I need to just let go. If everyone treated the opposite sex the way I did humanity would just die out because noone would take any risks. And it’s not like my passivity ever helped anyone in a visible way. But then if I try to embrace her “it’s just sex” attitude what is to stop me from becoming another shitty male out using and dropping women for momentary thrills.

I’m an adult and feel like I should have figured all this out but I’m just as confused and uncertain about it all as I was in high school. I acknowledge I have a history of unhelpful or flawed attitudes towards all of this. I guess I mostly just don’t understand hook up culture and because of that have a hard time knowing if she is someone I can trust to potentially have kids with. I’d hate myself if I ended up putting a child through the sort of childhood I had. Any advice, anecdotes or thoughts are appreciated.

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tl/dr: Best friend has a history of cheating on her partners with tinder dates with the excuse of “it’s just sex.” She’s been absolutely wonderful to me the 14 years I’ve known her. I’ve only had a few long term relationships. We’ve both crushed on each other but she’s been serious about me for a couple years and wants to date, marry and have kids with me. I don’t understand hook up culture and don’t know if I can trust her considering how she’s treated men in the past but I also acknowledge I’m an idiot when it comes to sex and dating.