Life's Awkward. Let's Talk About It.
Starting over at 40 isn't just uncomfortable—it's nakedly uncomfortable. Navigating broken hearts, midlife resets, and all the weird, unexpected moments in between..
Read My Stories
Starting over at 40 isn't just uncomfortable—it's nakedly uncomfortable. Navigating broken hearts, midlife resets, and all the weird, unexpected moments in between..
Read My Stories
After an unexpected content removal from our previous host, we're back with a fresh start and complete creative freedom...
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New content on the way...
New content on the way...
New content on the way...
New content on the way...
New content on the way...
Hey there! I'm Jake—overthinker, professional at making bad life choices, and full-time expert in awkward human existence. This blog started as a way to process all the moments that make me cringe, cry, or sit in the shower replaying conversations from 15 years ago..
I launched Jake's Awkward Days after my entire life imploded (see: betrayal, heartbreak, and a midlife crisis, but make it naked). What started as a desperate attempt at therapy has somehow turned into a place where we can all sit in the mess together—laughing at the ridiculousness of life, figuring things out one mistake at a time, and hopefully making it through with our sanity mostly intact..
Learn More About Me