Confessions of a Serial Dater

Description

Based on Journal Entries from 2005. The True Story of Love, Lust, and One Fantasy That Couldn’t Survive Reality.
For ten months, I built the perfect relationship with Tamia, a woman from Chicago I met on BlackPeopleMeet. We talked for hours every night. Sent hundreds of instant messages. Had phone sex left me convinced she was the one. I deleted my dating profiles, ended other relationships, and bet everything on a woman I’d never met in person.
Then, September 22nd, 2005, arrived. She stepped off a plane at LaGuardia Airport, and in thirty seconds, the entire fantasy collapsed.
This is the raw, unfiltered story of what happened next. We spent the weekend attempting to manufacture chemistry that wasn’t present. Brutal honesty destroyed the constructed relationship. The self-deceptions we had both maintained regarding our true selves and aspirations.
But it’s also the story of what came before: the months of juggling multiple women while claiming I wanted just one. The pattern of chasing perfection instead of accepting reality. The five-year search for an ideal that no human being could match.
Drawn from actual journal entries and told with unflinching honesty, The Chicago Connection is Book 4 in the Confessions of a Serial Dater series, a literary memoir about online dating in the early 2000s, when we built relationships through dial-up connections and AOL Instant Messenger, before smartphones and swipe culture changed everything.
Content Warning: This memoir contains explicit sexual content, adult language, and honest discussions of relationships, deception, and personal failure.