Enter Destiel
I return again with a question This may be a stretch but is there any fics where deans in a relationship with a girl and falls in love with cas and runs away w/him or leaves her for him?
No worries, this is not a stretch at all! Dean dating girls before he meets Cas is quite a popular trope in destiel fics. After all, that's canon. Here’s a small collection of such fics previously recced on our blog. I’ve selected fics where relationship with a girl is important to the plot and character development but of course, YMMV. I’ve also added fics with Cas dating a girl, since those are few and far between. And rest assured, there’s no girlfriend bashing in these fics. Sometimes a boy and a girl just don’t work out, right? Enter Destiel.
I. Fic starts with Dean or Cas being in a relationship with a girl (dating/ engaged/ married)
As We Forgive Those by AlreadyPainfullyGone (unofficially recced here) (Dean/Lisa, engaged)
Cas and Dean’s Infinite Playlist by kkingofthebeach (Dean/Anna, right after the break up)
Freebies and Oak Trees by violue (Dean/Tessa, living together)
It’s Always the End of the World Somewhere by scaramouche (Dean/Bela, dating)
Kind Of A Forever Deal by komodobits (Dean pursues Lisa)
Mr. Know-It-All by baba_writes (Cas/Anna, married)
My Heart Is Beating From Me by enochian things (Cas/Daphne, engaged, season 9)
On Air by wincechesters (Cas/Daphne, dating)
the open sky (is mine tonight) by weatheredlaw (Dean/Anna, engaged)
Painted Angels by winjennster (Dean/Anna, engaged)
Passing Ships by quiettewandering (Dean/Lisa, trying to date)
Peace and Good Luck To All Men by kismetjeska (Dean/Anna, dating)
So Glad We Made It by scaramouche (Cas/Daphne, dating)
Someone I Forgot to Be by mathildamavis (Dean/Lisa, living together)
Stellar (Meet Me In Outer Space) by youaresunlight (Dean/Lisa, dating)
Three Funerals and a Wedding by engaldnwouldfall (Dean/Lisa, Cas/Daphne, dating)
What I Need by xaandria (Dean/Cassie, right after the break up)
Genie in a Bottle by thepopeisdope NEW REC!!!! [NC-17, 30,000 word count] (Dean pursues Lisa)
When Dean finds (okay, steals) a bottle containing a strange, glowing blue substance, he does so thinking it's a cool novelty, at best. It didn't exactly cross his mind that the substance might be a living being, let alone a grumpy, sarcastic, perpetually-underdressed genie waiting for a new master. But now that he has a bona fide genie at his disposal, well-what better chance will he have to help things along with Lisa? Except, things don't always go as expected,
II. Fics where past relationship with a woman is described and has impact on Dean/Cas relationship, woman has either left or died.
Angel Cookies by noxsoulmate (widower, single dad Dean)
As The Sparrow by hubrisandwax (widower Cas)
Asunder by rageprufrock (widower Cas)
Autumn Hollow by shotgunsinlace (widower Cas)
Gargoyles on Motorcycles by mandraco (Dean/Lydia, single dad Dean)
Much More Than A Hunch by gedry (widower, single dad Dean, single dad Cas)
Novaks, Rebooted by violue (previously recced here) (Cas/Amelia, single dad Cas)
Plain and Tall by destielpasta and mtothedestiel (Dean/Lydia, single dad Dean)
This is All Life Really Means by gedry (Cas/Amelia, bad break up)
III. Since the ask is about Dean moving on from dating a girl to dating Cas, here’s some fics where relationship with the girl doesn’t fit in previous categories but is still important
An Assembly Such As This by unforth (Dean/Charlie, Cas/Anna, both marriage of convenience)
Diners, Drive-Ins, and Dives by cymbalism (Dean stays at Lisa’s, season 5)
Friends and Burgers by justkeeponwriting (Dean misunderstands Cas relationship with Anna)
Nine Times We Met (And One Christmas We Parted) by almaasi (marriage of convenience with Charlie)
Peanut Butter-Pumpkin Wedding Cake by sparseparsley (Dean misunderstands Cas relationship with Anna)
Someone Who’s Feeling For Me by ellispark (season 12 fic, Dean and Cas meet Lisa)
IV. More resources from our blog
for more fics with Dean and Cas being in past/oresent relationships with other people see our Tags Page, under Side Pairings header. Please note that sub headers Cas/Other and Dean/Other also act as tags for lesser used partners or original characters.
ask about Dean and Cas being in relationship with other people when they meet









