I live in Tampa, Florida. I am an underpaid lawyer-associate and I urgently need to supplement my income in the immediate future. For reasons I won’t get into here, asking for a raise is not an option, and I don’t want to try to find another full-time job right now. In my time I’ve been a librarian, newspaper reporter, and copy editor, plus the usual assortment of stupiddayjobs, including bookstore sales clerk. I have graduate degrees in law, journalism and library science, for what that matters in the moonlighting market. I used to free-lance as a legal researcher for other lawyers, but at present I can’t do any extra legal work on the side on my own account – anything I do as a lawyer belongs to my boss. Various “editing/writing” jobs I’ve seen on Craigslist seem to be aimed at people who will work for nearly nothing just to get published. A theatrical agent once suggested I try modeling, but I looked into that and you can’t do it if you’re only available nights/weekends. What can I do, that is not in the legal field, and can be done nights/weekends, and will pay enough to be worth my time? And what’s the best place to look for such work?
Avoid the whole last season after Maddy and David hooked up. Serious shark-jumping action.
I might be able to hook you up with a copy-editing gig – PM me.
Have you tried Mediabistro for freelance copyediting, or maybe cataloging work?
Any currently open categories at About.com fit?
ODesk has lots of jobs to bid on. A good portion of the postings are penny-ante gigs, but there are some decent paying ones if you have the specific skill set.
Am I the only one who checked the photo gallery after reading the modeling line?
Most libraries are open in the evenings, especially university libraries. There have to be any number in a metro area like Tampa that need part time help.
Snagajob.com is one of the best resources for part time work. I think any kind of job will be superior to trying to line up writing gigs. People sometimes forget that when you freelance, unless you have a rep. and people are sending you work, you spend a lot of your time trying to find work. That’s time you don’t get paid for.
edit - also try http://www.beyond.com/
Didn’t know we had a photo gallery. If curious, you can find my (now a couple of years outdated) pic on my Match.com profile. I was surprised when the lady suggested it, but apparently there is such a thing as “lifestyle modeling” for older models, and I sure don’t look my age (47).
You could join the National Guard.
ETA: Ooops, I think you’re too old. Sorry!
ETA2: Is anyone else burningly curious as to why the OP can’t ask for a raise and desperately needs money??? 
Kinda figured someone would say something like this!
No. Who can ask for a raise these days? I mean, you can ask, if you enjoy your boss laughing in your face. And perhaps you haven’t heard, but graduate education like law school sometimes comes with large loans that cannot be discharged in bankruptcy.
Bartending? Serving? I made some serious coin and most jobs are evening/weekends.
Freelance reporter for a weekly? Money wouldn’t be as good as the first suggestion.
Or that his day job sort of makes stripping cars and selling dope look less attractive than usual.
On the serious side I was going to suggest tending bar but be careful where. Having clients or people from other Firms see you at work can sometimes cause problems. If you have some skill in an area most folks consider a hobby (flyfishing for example) you may be able to use that to garner some bucks. When I guided one of the other guides was one of our areas top dom-rel guys ----- but with 8 kids spread over 10 years even that kind of income wasn’t going to make it and he knew it.
You put “Kneel in awe of my huge, hairy, throbbing, tumescent cerebrum!” in a dating profile? Really?
How much money do you need/want?
I worked at a gas station during my post-doc at night for 6-8 hour shifts. They seemed to like a smart person that was trustworthy. Paid like crap but for 50% of the time I was able to read papers for my real job and at $9 an hour, it was still an extra $600 bucks a month.
If you are in decent shape and can handle less sleep etc., night watchmen are another job where a decent sized guy is needed. THe only problem with these jobs is that they are going to be skeptical that you will stick around long so make sure you have a seamless story and say that it is close to your house and your other job is paying less but your mortgage is up, etc.
This:
Also other tip jobs like food delivery or valet parking attendant.
If you are available for early morning work, then newspaper delivery may be a good fit.
On a related note, those free papers/booklets/fliers that so many businesses have need to be delivered. An acquaintance of mine recently started doing this (evenings). His route is once a week. All he’s required to do is pick up the new papers from the main office, then drive to the locations on his route where he takes any leftovers from the previous week and replaces them with the current edition. He’s new and his route only takes ~2 hours. For this he is compensated ~$250.
Do you have a knack for teaching? Tutoring would be a good fit for your background. Building clientele as an individual would take time though. There are tutoring centers in many cities (like Sylvan Learning Center) but the pay would be lower.
Given your interests, how about being a part-time legislative aide? Or campaign staffer.
My biggest question was why the OP is seeing women 17 to 7 years younger than him, and not women his own age 
LSAT tutoring? Put up signs in the fancy private colleges and collect $50/hour.
(Plus it’s a great way to meet younger women. :p)
Is that actually something you can do for money, nights and weekends only, without quitting your day job or moving to the state capital?