Alright y'all, hear me out. Advice would be greatly appreciated, not just based on the title, but what I write in this post.

I'm 25M here, at the prime of my life physically. I finally feel confident, proud and happy in my own skin after overcoming a lot of mental health struggles and working out. I am a late bloomer with dating and such because of that, but not completely inexperienced. Anyways, I have some thoughts goin on...

1 (my crush):

So... there's this drop dead gorgeous woman (57, looks 37) that I know. She is a single mom with a kid around my age. She's a friend of my friend's mom, but I've gotten to know her over the course of my visits with my friend when she happens to be visiting my friend's mom at the same time. I genuinely enjoy talking to her and chatting, so it's not just me lusting quite. I've known and crushed on her since I was 22, but I just never knew if it was right to pursue this. I have a feeling she sorta likes me, she'll stare deep into my eyes when we talk, with a slight smile that almost resembles a smirk 😏. One time she said I had a nice skin complexion with this sort of shy and naughty look. I feel like there's some tension there but I can't prove it. Hypothetically, in the moment it feels like there's a 50/50 chance if I were to go in for a kiss lol ;) I could be delusional.

2 (potential escalation): I'm aware there is a significant age gap, so I know it's a bit tricky when navigating flirting and what not. Cougars, what do you personally like and expect out of men in their 20's? Have I already missed the boat by waiting around? Our vibe hasn't changed.

3 the future):

I hear that some cubs regret going for a much older woman because they didn't spend time investing with a younger woman and starting a family when they were younger. Since I'm somewhat inexperienced, time creeping up on me scares me a lil bit. Will I later regret not being with people my age? I also find them attractive. The "you're only young once" thing messes with me a bit too.

Also will it be awkward for her son, my friend and her mom if I escalate this? Is it disrespectful or risky? Sorry if that's a stupid question; I just don't want to bark up the wrong tree.

Thanks to those who read this. I'll respond to each and every one.