Families meddle, in general. That's drama we both want to avoid. I meant to say: it's not just about us hanging out, if the family gets their noses involved. Though my family isn't meddlesome, I think hers is. So that's something to be avoided.
My previous relationships matter since someone in her family knows I tend to be a dump and run kind of guy, though I'm starting to try and change my ways, to think and act differently. Still, it would be natural for my sis-in-law to want to protect her family member from my wicked ways. Let's say you had a brother who women fell for, but you knew that he was just out to get laid, and was a complete disaster (not saying this is me, btw) when it came to anything long term. Would you be comfortable setting him up with a very good friend of yours? Likely not.
There will be no confrontations or drama. We're going to get together. We'll talk. Hopefully I made more out of it than it is.
Of course there are insecurities. Yes, age matters. A few years ago there was a 28 year old who approached me. We went out, had an amazing time. Wasn't long before she said "if it weren't for the age difference, I'd totally want this to continue." So yes, past experience plays a part.
You may be right about the window closing. I can't tell you how many desperate over 45 women I know, who seem to have everything going for them...except no man.
My hesitance to fvck due to her weight was where all this started. It's entirely possible that it may still be where it will end. Still, my personal experience has shown me that when I sleep with someone right away, the likelihood of there being anything lasting goes down at an exponential rate. We've been together four times, and that is on the edge as far as how many times I've gone out with anyone without going the distance. If it doesn't happen this time, it probably never will. So there's that.