With reference to patio11's comment above: Your talking point is "I want to write some code in Python for your company."

Then, if and when they turn you down for that job, you can approach the CEO at one of those local meetups and say, "Hey, I'm trying to become a better programmer; what should I study next? Here's a couple of my projects on Github so you can see the sort of things I've been working on."

You keep talking about how unqualified you are. Perhaps you are merely too shy. But if you're certain that you don't know Python well enough to write code in Python for money... learn more Python! You will have to teach yourself, of course, using books and blogs and example code from Github and Stack Overflow and semi-random Googling and surfing through your system's source code. You will have to get used to that: Web programmers are autodidacts, as they have had to be since the Web was invented, and as they will continue to be for at least another decade.

My friend & mentor keeps telling me to quit being a wussy and that I'm about as skilled as he was when he was a fresh graduate. I need to put on my big boy shorts and just apply. I am an enthusiastic autodidact so no problem there.

In my case, it was a requirement that I spend like 40 hours doing volunteer work at a homeless shelter or similar for a class on homelessness and public policy. The class was online through a San Francisco college but I was in Fairfield, about 45 miles away. So folks actually in SF had a list to work from to seek internships. I had to find my own if I was going to do something local. I went and asked to speak with the director and explained that I needed this for the class, when I could be there, some of the things I could offer, etc. I had to get a drug test before they would say "yes".

Since you don't need this for a class, you will need to be a little more convincing. "What color is your parachute" may be helpful in that regard. I would go talk to the guy in charge and tell him what you have told us: "I really want to do X with my life and am changing careers. Your company is the only one in the local area doing stuff I find really interesting. I would love to have the opportunity to spend time here and learn from people who are smarter and more experienced than I am. I am willing to do whatever you need done that will let me spend time here. I am willing to do so without pay if there are no current job openings for which I qualify. Is there any way you would consider letting me do that?" It might also be helpful to mention that you are aware of monthly meetups but scheduling conflicts do not allow you to attend. You should be prepared to state what times you are available and how many hours per week you can commit to this. If turned down, be very gracious about it and thank him for his time. If you do get turned down, if possible, close with "Keep me in mind if you change your mind/if something changes/whatever the appropriate remark is for how the conversation went (ie the stated reason for saying no)."

Thanks for the longer explanation. I lived in Santa Clara until about 8 months ago, and visited Fairfield regularly for work. I know exactly how remote it is (relative to the Bay Area), so big ups on taking your ass to the city for an internship.

I'll keep your words in mind as I prepare what my email/remarks. Thanks.

Thank you, though I actually took my arse to Vacaville, which is about ten miles up the road. I bought them this domain name: http://www.opportunityhouse.us/ Their website has come a long way in the time since then. They developed a lot in the time I volunteered there and the director did indicate that it helped enormously that I helped them streamline their paperwork and cut many man-hours from the process of keeping it up to date each month.

Good luck with your search for an internship.