Ongoing4h 55m
Last published Tue, Jul 14, 2026
🏆 Watty Award Winner (2022)
This updated edition includes revised chapters and new scenes.
Trans guy Collin makes a bet with his coworker that he can land a date with the hot new barista across the street.
It should be easy.
Except the more time he spends with her, the more the bet starts to feel like the worst idea he's ever had.
###
It's 2003 in Santa Cruz, and 21-year-old Collin thought transitioning would be the hard part. But now that he's on hormones and passing with ease, he's still stuck wondering who he is and where he belongs. It doesn't help that his girlfriend of six years just dumped him.
So when his coworker challenges him to prove he's still got game, Collin agrees to a stupid bet: get a date with Heather, the cute new barista who just started working at the café across the street.
With some unexpected help from his roommate Sam, getting close to her might be easier than Collin expected.
But what starts as a harmless distraction quickly turns into something real.
And when the truth behind the bet finally comes out, Collin will have to decide whether risking his heart again is worth it... or if he's about to lose the best thing that's happened to him since the breakup.
A nostalgic beach-town rom-com about bets, baristas, and what happens when pretending turns into something real.
☕ Tropes: friends-to-lovers vibes, a very bad bet, coffee shop flirting, early-2000s nostalgia, and learning who you are while falling in love.
NEW CHAPTERS EVERY TUESAY & FRIDAY
All Rights Reserved
#65
breakup
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