Sexual Encounters

Sexy times in the Impala with Dean and Anna

This is intended to list all known sexual encounters by Dean, Sam, Castiel, and Crowley, including those only mentioned but not seen on screen. Sexual encounters include any consensual sexual contact.

For outcomes of Sam's encounters check Peen of Death.

Dean

• Haley Collins - 1.02 Wendigo (kiss)
• Andrea Barr - 1.03 Dead in the Water (kiss)
• Cassie Robinson - 1.13 Route 666 (sex)
• Kate - 1.20 Dead Man's Blood (kiss)
• Crossroads Demon - 2.08 Crossroad Blues (kiss)
• Waitress in Tampa - 2.09 Croatoan (mentioned)
• Tara Benchley - 2.18 Hollywood Babylon (sex)
• Carmen Porter - 2.20 What Is and What Should Never Be (sex)
• Starla - 2.15 Tall Tales (kiss)
• Crossroads Demon - 2.22 All Hell Breaks Loose: Part Two (kiss)
• "Doublemint Twins" - 3.01 The Magnificent Seven (sex)
• Lisa Braeden - 3.02 The Kids Are Alright & Season 6 (sex)
• Thai masseuse - 3.06 Red Sky at Morning (mentioned)
• Jamie - 4.05 Monster Movie (sex)
• Anna Milton - 4.10 Heaven and Hell (sex)
• Amanda Heckerling - 4.13 After School Special (kiss)
• Unnamed Teen Girl - 4.13 After School Special (kiss)
• Tessa - 4.15 Death Takes a Holiday (kiss)
• Meg - 5.01 Sympathy for the Devil (kiss)
• Rhonda Hurley - 5.04 The End (mentioned)
• Risa - 5.04 The End (mentioned)
• Jane - 5.04 The End (mentioned)
• Dean's hand - 5.06 I Believe the Children Are Our Future (mentioned)
• Jo Harvelle - 5.10 Abandon All Hope... (kiss)
• Wendy - 5.11 Sam, Interrupted (kiss)
• Pamela Barnes - 5.16 Dark Side of the Moon (kiss)
• Lydia - 7.13 The Slice Girls (sex)
• Annie Hawkins - 7.19 Of Grave Importance (mentioned)
• Ellie - 8.14 Trial and Error (kiss)
• Robin - 9.07 Bad Boys (kiss)
• Suzy Lee - 9.08 Rock and a Hard Place (sex)
• Anne Marie - 10.01 Black (sex)
• Shaylene - 10.07 Girls, Girls, Girls (kiss)
• Heather - 11.04 Baby (mentioned)
• Bar Hook-up - 11.04 Baby (mentioned; mistakes were made)
• Amara - 11.09 O Brother Where Art Thou? (kiss)
• Valentine's Day Hook-up - 11.13 Love Hurts (mentioned)
• Melissa Harper - 11.13 Love Hurts (kiss)
• Elka - 12.11 Regarding Dean (sex)
• Carmen - 12.18 The Memory Remains (sex)
• Exotic Dancer - 13.05 Advanced Thanatology (unknown; but it was probably fun)
• Cartwright Twins - 13.16 Scoobynatural (mentioned)
• Triplets - 15.07 Last Call (mentioned)

Sam

• Jessica Moore - Pre-series (sex)
• Lori Sorenson - 1.07 Hook Man (kiss)
• Sarah Blake - 1.19 Provenance (kiss)
• Madison - 2.17 Heart (sex)
• Bela Talbot - 3.10 Dream a Little Dream of Me (sex dream)
• Ruby - 4.01 Lazarus Rising & 4.09 I Know What You Did Last Summer (sex)
• Dr. Cara Roberts - 4.14 Sex and Violence (sex)
• Wendy - 5.11 Sam, Interrupted (kiss)
• Crystal - 5.12 Swap Meat (sex) while Gary Frankel was in his body (not like that...)
• Lana - 6.03 The Third Man (sex)
• Sparrow Jennings - 6.09 Clap Your Hands If You Believe... (sex)
• Debbie Harris - 6.13 Unforgiven (sex)
• Nicole Handler - 6.13 Unforgiven (mentioned)
• 3 Unnamed Women - 6.13 Unforgiven (mentioned)
• Amy Pond - 7.03 The Girl Next Door (kiss; flashback)
• Becky Rosen - 7.08 Season Seven, Time for a Wedding! (kiss)
• Annie Hawkins - 7.19 Of Grave Importance (mentioned)
• Amelia Richardson - 8.06 Southern Comfort & 8.10 Torn and Frayed (sex)
• Piper - 11.04 Baby (sex)
• Unnamed Teen Girl - 11.10 The Devil in the Details (kiss; flashback)
• Lady Antonia Bevell - 12.02 Mamma Mia (hallucination)
• Velma Dinkley - 13.16 Scoobynatural (kiss)
• Eileen Leahy - 15.09 The Trap (kiss)
• Eileen Leahy - 15.14 Last Holiday (date and possibly sex)

Castiel

• Four Women - 5.04 The End (presumptive orgy as Future Castiel)
• Meg - 6.10 Caged Heat (kiss)
• Daphne Allen - 7.17 The Born-Again Identity (presumptive)
• April Kelly - 9.03 I'm No Angel (sex)

Crowley

• Mr. Pendleton - 5.10 Abandon All Hope (kiss)
• Bobby Singer - 5.20 The Devil You Know (kiss)
• Lola - 9.16 Blade Runners (sex)
• Marnie's Husband, Deb, & Dale - 11.01 Out of the Darkness, Into the Fire (orgy)