How Can I Communicate This Without Sounding Like A Tool

Not really - when I call alums I never ask for a job, at least not until I've given them a reason to like me, and then they may offer one without my asking. You can obviously drop hints, but I don't think there's a magic word - it is rather presumptuous to just say, "I'll work for free," and is going to make them feel awkward. Talk about how you want to get experience, how you have been looking for an internship but been unlucky, ask how they got started, etc.

yes - do not flat out ask for a job. worst mistake you could make is contact/email them with your resume when they don't even ask for one.

To your alumni, I agree with what Leggo said

With someone not from your school and just cold emailing? I would suggest state what you want, be polite, and attach your resume.

Working for free should be a last resort. For example, when they say "we are not really looking to pick up any interns this year," you can bring up the idea of working for free.

thanks guys

i havent been talking about it from the get-go, was mostly wondering how to work it into the conversation. more of a problem wording the phrase "i will work for free" than anything else. i would never presume to send my resume and start asking for a job right off the bat

Try "I'm focusing this summer on getting an opportunity to learn as much as I can, and am not too worried about getting paid"