Ask HN: I’m 41 and still unmarried – what should I do?

"...second chance..." You're keeping a tally?

".. I sanity check it with my friend." You have the capability of discernment on your own, and you should engage with owning your own power and capabilities. Going to a friend is you trying to export the potential guilt/shame/pain/whatever-negative-feeling-you're-avoiding out to a 3rd party as a safety valve so you don't have to deal with it when the (surprise!) inevitable happens because there are now no consequences for your actions.

"I'm not the kind of person..." Whatever was in the rest of that sentence, you should try to be that kind of person for a while. To get some perspective.

"I try to be compassionate and see the good in people." Oh this is a giant red flag. If you feel compelled to wave this banner around (especially in public), as though other people 'are not' this, it is because you likely have a crushing amount of guilt from being judgmental about others.

"I've endured a lot of negative treatment from men" You mean like they beat and rape you, or they call you names and yell at you? There is a chasm of difference between these two things. If you're summoning assholes from the first group, god help you. I hope you can find a mentor that can restore your confidence and you can come to know that you intrinsically have worth that is outside of whatever horribleness you are encountering in the world. If you attract men who are verbally/psychologically abusive, then I would suppose there is a reason you are attracting those kind of men. Maybe you are a negative, spoiled, titty baby who constantly plays the victim card and incessantly puts the blame for your situation on others because you're afraid of responsibility. Maybe you've lost (or were never taught) the value of having gratitude, even (and especially) during trouble.

Your expectations of people are worthless, no, worse, they are actively destructive to your relationships. Any expectations of people are that. Assume all responsibility, even for others, yourself, or continue driving in circles.

the only way out that i see is that both partners recognize the challenge and find the opportunity to work through these questions together, which btw is already a good way to work out if you can cooperate.

being able to cooperate, for me is now the most important quality in my relationship. if we can work together on reaching each others goals, we can solve the problems that get in the way.

ironically that is the same quality that's most important in the relationship of company founders.

i disagree. that is something that i would want to know up front. yes, it may put off some people. but if the person is put off by that they are not likely to be a good candidate anyways in my eyes.

if you really want kids, then time is running out, and both need to be aware of that. i'd consider not stating that up front but bringing it up later an unfair bait-and-switch. if both are not on board with taking this biological limitation into account, then that's not going to work.

He said something that's a common expression, "taken", which is used for both men and women. It was clearly intended to be a compliment.

You chose an unlikely interpretation that clearly didn't match intent or common usage and decided to get offended about it.

After all your self description, I was wondering "how is she single?"

Right there, now I understand. I'd be out the door. Someone that is looking HARD for ways to be offended is not relationship material.

Think about your need to assign your meanings to other people's words. Maybe talk to a professional. This one thing can sink you.

Good luck!