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A little humor sprinkled in a resume. Yay? Nay?
This shouldn’t be news to people but it is.

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It might be worth looking at your resume and having someone review it to determine if there are specific areas you need to improve upon. How many applications are you submitting a week? If you're not hitting at least 100 a week then I'd say continue with the online apps before reaching out directly to agencies.
Personally think there's nothing wrong with looking "desperate" especially since it would only be the first time you're reaching out! Shoot your shot, and don't give up hope, even an entry-level opportunity could take you to the next level in your career, you never know!
I’ve seen a lot of people with gaps take free online courses and start adding those to their LinkedIn/res and see positive results. Plus it keeps your current and gives you something positive to speak about in a job interview
I woudl say do it. Also if you can get a personal referral that works well too.