I (late 20s M) dated a widowed single mother (11 years older) for over a year, and she had a young child who I have known for most of his life. We broke up basically because I was recently out of grad school and also felt like she never had the opportunity to properly grieve, but I already feel like I've had an exciting and adventurous life, and besides, I love them both dearly, and separately could use a little more structure and family in my life. We took a period of no contact and then another several months of platonic friendship to grow independently and give each other space, and now I feel like we're closer than ever and have started almost seeing each other again. She knows me like no one else and I dream about both of them almost daily, and they've (welcomely) infiltrated so many aspects of my life. I know most of her family and she knows all of mine as well.

The biggest fear is of course related to the biological clock—I didn't feel ready to be a father when we first met at all, although I knew I wanted to be one someday of my own biological kids. She did an incredible job at keeping space between her son and I originally, but as our lives got more intertwined I started spending more time with both of them together, and now take him to the playground sometimes as a manny and just love every moment I get to spend teaching and learning from this little man! I really struggle to remember that he's not my son sometimes. As for more kids, she has frozen eggs recently, but we'd prefer natural if it comes to that and we're both healthy 😅

I also fear my dumb man mind and lack of commitment ability will bite me in the butt as well. I feel every day that this is less of a factor but I'm bisexual and we both have heavy dating histories-- serial monogamists with eras of intense and immense exploration, and are open to prospects of openness in the future, but neither of us wants that with each other especially off the bat if we start dating again. We have amazing physical chemistry and in most ways make sure our needs are met, and are fantastic communicators (to the point where she's more than trained me to be an oracle of communication skills in my friend groups of peers that are closer to my age 😂).

Additionally, professionally, my "dreams" might have me relocated or traveling the world a little more, but I feel like I am fortunate enough to have gotten the travel bug out of me a long time ago. We are also in a major city and things are more than capable of happening for me here, just potentially harder than some others. This is also secretly a big point to me, but my profession will likely also lead me to be in the public eye a little more, which is something I know she doesn't want for herself and I also wouldn't want to force that on her child by any means.

We both have savings so there's no insane economic imbalance, we have difficult but present relationships with our families, and we just fiercely and overcalculatedly want what's best for each other. I fear trying to date more seriously and taking more time away from her from finding someone who can be more reliable and compatible in their phase of life, and I don't want her son to feel like he was abandoned by two father figures so early in life. However, even in the time since we've met, I do feel exponentially closer to the person I've been shoving myself out of the picture for.

This is also a whole separate conversation let alone bullet point, but I've also had some fears lately about how if we have more kids they would interact with each other.

I would love to know your thoughts on if I'm crazy for entertaining this, if I'm crazy for waiting so long, or if I'm just crazy for coming to strangers on the internet for the validation my therapist can't give me. Please feel free to ask questions, and I appreciate your time! :)