To ask how it feels if you wanted marriage/children and it never happened?

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I’ve found over time that one of my oldest friends is starting to pull back from our friendship and if we do meet takes very little interest in my family life. It started when I got married and since I have had children it has got worse. I know my friend desperately wanted to get married and have children and she has said before when I tried to talk about it once that she is happy for me that I am living “the dream” we had as young girls. She was stuck in a bad relationship for many years with “the love of her life” so it has never happened for her and as we hit 40 and she is still not over him, I think she’s giving up hope. She is very closed off about her feelings and I know she would deny that there is any envy if I did try to raise it with her. Sadly, I think the friendship is reaching its end and I think I know why even though it’s not out in the open. I guess because she will never talk about it, I thought it may be helpful to hear from anyone else who is in the same position she is in, so that I can maybe try to make some sense off and peace with what’s happening, if that makes sense. I imagine it is extremely painful to not realise the biggest dream you had in life and that can change you as a person and make it harder to be around families?

It feels fine, actually. Except, I find that my friends who are entirely focused on their families and children are not very interesting company.
Two of my best friends have kids and both went through stages of hyper-focusing on their family life at the expense of everything else. At that time, I very much pulled back because I have little interest in Andrew having cold for the sixth time this year and Helen having a rough time in the nursery again. Once my friends got back to work and started socialising without kids, we could resume going to theatre and having grown-up meet ups which involve cocktails and chatting about current affairs. We are closer than ever and are planning to take a girly trip in Spring sans children and husbands.
It's not being around women with family that is hard, it's losing common interests with your friends when their priorities shift. I probably wouldn't be quite so open as you about you feeling sorry for your friend either. You are only reinforcing whatever feelings she may have. For all you know there maybe nothing at all she regrets and finds you coming back to this conversation all the time off-putting. It's also a possibility.

What's the point in this post, OP?

It's heartbreaking. I can't even think about it too much because it makes me so sad. I don't care about not being married, but I really wish I'd been able to have a child of my own. It really gets me when I see mums with little girls who look just like them as I always dreamed of having a daughter.
But I still manage to be around my sisters and my friends and their families. I love spending time with their kids and watching them grow up.

She is very closed off about her feelings and I know she would deny that there is any envy if I did try to raise it with her.

Then I would respect that, OP. She doesn't want to talk about it.

Why do you think the friendship is ending?

I always thought I would have more children, but it didn't happen, and I do feel sad when I hear about other people having children. It pulls again at my grief for the children I won't now have.

Personally I have found that spending time with niblings is rewarding more than upsetting, especially now that I have spent enough time with them that they trust me enough to talk and play with them.

I’m very conscious about not boring my childfree friends with details about my children (but they do exist and they are a part of my life) so I don’t think that’s the issue.

I’ve never actually broached this topic with her because I don’t think it’s for me to raise. I know she has always been a bit competitive with me in other things. There have been other subtle signs eg she has mentioned a falling out with her sister over the same thing and was quite miserable on my wedding day.

I do think for someone whose life has centred around this dream it probably is a type of grief that is not really spoken about