No income, no job prospects, and no possibility of unemployment benefits. Help me.

I have training in this area - the 'gaps' had to be addressed and your answers were helpful for me to properly advise you. I do not care, nor pass judgment on your decisions - we are all commonly united this way. My 3 suggestions: Forget Temp agencies - they are flooded with people with loads of experience. Instead, Craig's List offers you the a better, quicker route (you are fortunate to be in a city like Chicago in this regard). Stay away from the contract positions (easy to get, no weekly salary and no health). Second: apply to companies with 30 or less employees only - no HR. No gatekeeper. Stick to Business Writing and PR positions (brochures, whitepapers, marketing materials, handbooks, proposals, etx). Do your research - get the name, and email them with a specific value to their company. Repeat. Again, you have a lot of such companies in Chicago. Third: Apply to well known Insurance companies (Life and Health). They will train you with pay up to 6 mos, plus commissions. What they pay matches your weekly need. You do not need any experience - they will train you for an exam as well. They take English majors right from school all the time. It's an office job, and it offers health insurance. If you don't like it, use it as a stepping stone. Good luck.

Something doesn't add up. You've been in school for your 2nd Bachelor's for almost 6 years? When you were getting close to graduating, no job placement was made available to you through the school? Your 2nd degree is in English - you must have chosen that with deliberation (after all, you went back to school for it). What types of jobs did you plan in mind with this degree? Did you apply to p/t jobs where no/or basic resume is all you need? It sounds like you "suddenly" found yourself with no money ir job in the near future - but you had to see it coming. Additional insight to this may help in advising you in much more concrete and helpful ways.

A few suggestions: 1) Your "household size" is probably one, not two, unless you claim your roommate on your tax return somehow. 2) The gap in your resume should be explained in your cover letter. You've been in school. Have you been doing anything since you graduated? Volunteer work, caring for a relative, travelling, anything? 3) nthing temp agency. Temp jobs can quickly lead to permanent jobs, and will stop that gap in your employment from getting any bigger.

It might be a longshot, but have you looked into teaching residencies? Many cities with "inner cities" have them, and they allow you to get certified (often for free) while working as a teacher for pretty good wages. This is one area where your recent BA in English combined with "life experience" might be seen as an asset rather than a liability.

Awkward Engineer explains a great way to get past the resume straight to the interview. http://www.awkwardengineer.com/2012/01/more-job-hunting.html. http://www.awkwardengineer.com/2012/02/how-to-stop-dealing-with-hr-and.html. But when you do this, please be more relaxed, prepared, and less defensive than you are in your responses here. I understand that you're very stressed, but you'll never get a job if you're this twitchy. Queue jumping will only help you if you're confident, or can at least fake it for a few minutes.

OP: No worries, I get it. There are a number of industries that do not care if you don't have experience: all they want is to be able to train you. And for that, they need a college grad that is capable and eager to work. Insurance companies, Retail exec programs, Financial Advisor training programs, Car sales, Telemarketing, - all paid training with health. Insurance companies: you're looking for 'become a licensed agent' jobs (some who take inbound calls from customers and take orders for property insurance. Others, such as life/health insurance may go out to see clients). The point of insurance is they need licensed bodies, they will hire fresh grads with no experience, and they training is paid, along with health insurance. Business writing jobs: Do a combo effort. Look on CL under writing-related terms, but also make a list of local Chicago companies that are small (use Inc.com to find these), less than 30 and approach them for a marketing *assistant* position. Assistants do a lot of the copy for websites, brochures, trade show material, you name it, - and every company needs this. $500+ a week, health insurance. Very important - do not sound desperate in the initial contact with companies. Get to CL 1st thing each morning, and email those 30-employees or less company execs every day before 9 am to get noticed quickly.

HTML/CSS aren't that hard to pick up. Really. Hell, you can learn it online at http://www.w3schools.com/. And to some degree, Office isn't that drastically different either. Mostly you'll just be going "where the hell do I find the insert section?" a lot. If you can get a hold of or borrow someone's computer, you can probably mostly figure that out for yourself too.

Have you tried sending out a version of your resume that clips your early experience and first bachelors degree? It strikes me that HR folks might have an easier time understanding "I worked from 2001-2006 as a webmaster and content producer for Big Megacorp, then went back to school to get a B.A. and have recently graduated and am now looking for a new job" versus a resume that raises questions about why you went back and got a second BA. Not sure how your age scans when people meet you, but for many people it's pretty difficult to tell the difference between 30 year olds and 40 year olds, so it might be possible for you to "pass" as someone who worked for a few years before going to college and getting your degree. I don't think any expects resumes to be exact histories, and I suspect that hiring managers aren't sure how to interpret the second degree so long after the first. By shaping it into a more conventional narrative, you both sidestep the question of "why did this person go back to school, did they get fired and were unhireable and that's all they could do?" as well as neutralizing somewhat any sort of age-discrimination factor that might be going on, where people don't want to consider a 40-year-old for an entry level position. At this point, if you're not getting any nibbles with your current resume, I think it's likely that everything before about 2001 on your resume is hurting you more than it's helping. Chop it off. If you interview well, then by the time people are quizzically looking at your grey hair you'll have already made it past the HR hurdle and can explain your varied work history in a way that is flattering rather than confusing or offputting.

Lie about this: 1) My office software skills are woefully out of date (the last time I had to work with MS Office was 1999). It's really basically the same especially for the stuff you'll be doing re: temp jobs. Also being in school should be listed on your resume as full time school is a substantial commitment. Also you're a theater guy? Got any friends on the tech side of things that can get you on freelance load-in calls?