My problem is I don't know how to talk to anyone outside my social circle, and also the dreaded notion of approaching someone many years younger and appearing like a creep.

I can easily strike up conversations but not good at turning that into anything more. And the few I manage to hold a conversation with either see me as a good friend or lose interest.

And that's why I'm here to learn the game.

Welcome to the forum, Hank. Hopefully we can help you iron out your issues.

Are you trying in person and online as well? Where are you doing your approaching? Is it day or night?

Your fear of coming off as a creep is all in your head. Women are generally flattered when you speak to them or smile at them... Even if they reject you. Everyone likes being hit on.
A LOT of girls go for slightly older guys too (my girlfriend is 26. I'm 36). Don't be afraid to risk being seen as creepy, man... You'll never see these people again anyway - so put yourself out there.

You may not be escalating while you're talking. You need to identify yourself as a sexual option and make your intentions clear (without actually making your intentions clear... I know it's confusing). Don't say you like her. Show her you like her. Touch the small of her back, or her arm, or her leg (not in a creepy way) and use kino wherever you can... Smile. Eye fuck. At the end of the conversation, instead of saying goodbye, you say "Hey you seem like a pretty cool girl. Let me get your number" and hold out your phone.

Spot on advice from Charles as usual - do what he is saying to do OP.

OP if you look young as you say you do, that's even more reason to not feel that you're creeping on the girls.

Try not to be nervous when you "approach" them; just embark on a regular casual conversation. Remember, you're not tryna get anything from her, you're just shooting the shit to begin with.

I don't know how to approach those outside my social circle

welcome to the meetup, as you can tell there is a lot of great advice here

Thanks

One thing I struggle with is revealing my age. Most of the time they never ask because it never occur to them to ask.

But sometimes they do, especially after we've talked a bit.

They'll go, "You seem a lot more experienced and mature for someone in his 30s. How old ARE you?"

Or it may go something like this:
She: "How old are you?"
Me: "How old do you think I am?"
She: "Mid to late 30s?"
Me: "Then that's how old I am."
We both laugh.

Sometimes it ends there, but sometimes they press on for my my real age.

What should I do? Come clean, or continue letting it be a mystery?

a friend of mine that goes to the pua meetup group i run is 49 years old and he consistently fucks women my age (I am 23)

so age is not the issue... its actually a shit test. don't answer the question but instead just break rapport or ignore it then change the subject

I agree w/ Andy.

Dude the primary reason they are asking your age is because you are hung up on your age. When you stop giving a fuck about that and realize you are two humans they will stop asking about your age. You are giving off insecure vibes to them because you feel like a creeper around them. Just stop that. DO YOU THINK THE SENIOR CITIZEN MEMBERS OF SOME ANCIENT ROCK BAND FEEL WEIRD ABOUT THEIR AGE WHEN A BUNCH OF EARLY 20s GIRLS COME BACK STAGE WANTING TO HAVE A LIL FUN? So just forget this notion of your age and see if the girls don't forget it as well.

Another hangup I have is my glasses.

I am long-sighted, and I can't see anything near without my glasses. And there's no contact lens for long-sightedness.

So I end up not doing anything that will require me to read anything. Sometimes a girl would show me something on her phone which would force me to take out my glasses to see what it is, and it shows my age.

Anyway to turn this around?