I'm not really seeking advice, just sharing recent experiences being back in the dating game for the first time since 1991. I was seeing someone exclusively then married them, lasted 17 years, then separated, later divorced, and in a relationship for 2+ years.
* My post-spouse relationship with with an older (50) woman, never married, no children. I'm not sure this was all that was involved, but conflict with my ex-wife, and her inability to integrate with my kids were big factors in killing the relationship. Now, mostly talking to and dating divorced women with kids, I see how frustrating it can be; like when someone lets their ex control their free time. On the other hand, being in those shoes, while it's frustrating I don't let it get to the way a single, childfree partner might.
* I recently was on the end of doing the breaking up for the first time (at least that I can remember). My last one broke it off with me. With my wife is was pretty much mutual. We were already living apart and went out to lunch one day to discuss things, she said "I think we're better friends apart than together." Since the breakup of my last relationship I've been out with 4 women (still talking to 1, the others didn't go anywhere), and talking to half a dozen others plus just getting out with friends about every weekend. I started talking pretty seriously with one woman a couple of weeks ago, a little long distance and due to other plans we had our first date out just coming up soon. Then the red flags started coming up. No one thing I couldn't handle, but the more she opened up to me about her life, and the more I asked about things that might be a concern, the more the warning the bells sounded. To shorten a long story, I finally broke off the date, blamed it on myself not being ready to move on yet and lacking the finances at the moment to maintain a long distance relationship, and her first reply was friendly, "take care of things and talk to me when you're ready" then suddenly she switched to psycho mode and finally said she was blocking me and don't think about contacting her. I told myself, "whew, you just dodged a bullet there. suspicions of mental health issues - confirmed."
That said, it wasn't easy.