I need HELP PLEASE. What's age appropriate?

I've been married and completely out of the game for 20 years. I appear to be in my early 30's according to most (and that's cool that people say or think that), but I'm actually 40. I'm not the old guy just looking for sex, I want to hang out and have fun too. How can I know when a girl I'm talking to (more specifically a waitress that's obviously at least 10 years younger than me) isn't just being nice to the older guy? or how can I determine attraction without becoming the old weird perve?

the only thing one person needs to be adventurous, cool and interesting is actually doing those things. Rebuild yourself into a better person. enjoy the world and enjoy your life. Take hiking trips, get in shape, do extreme sports, visit the world and become a knowledgeable person, DO COOL STUFF. All that will help you become an interesting person.

BTW, what do you want? a soulmate? truckloads of sex? or just to have fun?

Thanks for the reply. Soulmate, lots of sex, loads of fun... yes more please. I started weight lifting/getting in better shape a couple of months ago and definitely having noticeable results. In fact for the first time in a few years I'm actually seeing women notice or glance at me more (unless I'm finally at a life continues point of being ready for it, because I did go through a bit of depression)...

I'm just not sure how to respond sometimes for fear of looking like a creepy weirdo or appearing too wanting... for example, yesterday I'm in the grocery store and strolling toward the checkout (which is only about 5 feet away) when I see a beautiful woman pushing her buggy past, we make eye contact, I see a subtle smile as we pass and as I get to the register I look back and before she turned on the aisle she was moving towards, we made eye contact again and she had a little more of a smile. She was wearing a pair of jogging pants, t-shirt, very little make-up, hair was up (my thought was she was not expecting or out to meet someone), but she was still hot... Dressed up and ready to go out she could easily be an 8, maybe a 9.

What did I do? I stood there at the register thinking about how I didn't notice if she had a wedding ring on (because that matters to me), and wondered if I would ever have another opportunity, and if I did would it go the same way or would I approach her and say something witty or what?

I'm just not sure what to do in different situations. Any proven techniques, scripts or suggestions?

sometimes the most simple of things open up the biggest oportunities:

Hey (or hi) going for a jog afterwards OR

hi do you go into X Gym? turn it around however you want and start to convo, the more times you try and fail, the more you will learn and the better you are going to get.

just start the conversation and get it going. being interesting as i told you before helps a lot on being able to talk and having interesting topics.

I think assessing the level of attraction in your target is something which is definitely non-specific to your situation.

PU dogmas usually tell us to keep our intentions indistinct until we believe she is attracted enough.

More specifically to your situation, I can tell you I'm almost 30 and have been making out with a couple of girls aged 17-18 (age of consent in my country is 16, so nothing illegal here). I don't have a lot of experience with this, but I feel the way to go is simply to ignore the age issue altogether. From my (small) experience, the more she delves in the age issue, the more it becomes detrimental to you.

If she raises the issue, try to ask her what she looks for in a guy, pick the points that apply to you, explore them for a short while but change subject ASAP. Alternatively, focus on these point in a broad manner that has nothing to do with your or her age. If you do decide to change the subject, do it in a way that is not perceived as if you're trying to avoid the subject (e.g. try to do a spontaneous change of subject).

Whatever you do, don't think of what you're doing as being weird or something you need to make excuse for -- this will reflect in your state and frame.

Once again, I don't have a lot of experience with this, but hopefully this will be of help to you.