After years of obsessing over The CW's hit TV show Supernatural [1], you start to learn a few things. For one, there will always be plenty of steamy pictures of Sam and Dean [2]. What's more, the Winchester brothers are the best and baddest duo on television [3]. But the boys aren't the only reason fans tune in week after week — there's one demon who never fails to make us laugh. That's right, we're talking about the one and only king of Hell, Crowley (Mark Sheppard). To help commemorate our love, we're using iconic Crowley GIFs to guide you through the shortcomings and pitfalls of your 20s.

When It's a Week Before Valentine's Day and You're Single AF

When You're Trying to Flirt at a Club but You Actually Can't Hear Anything

When Everyone in the Squad Is Busy on a Friday Night

When Your Friend Accuses You of Having a One Night Stand

When You Sit Down at Brunch With Some Really Good Tea to Spill

When Your Mom's on the Phone With Grandma and She Makes You Say Hello

When You Go to Canada For the First Time

When Your Friend Wants to Get Revenge on an Ex

When Bae Asks If You Want Cheese on Your Fries

When Your Friend Says You've Had Enough Tequila For the Night

When You've Resigned Yourself to Life as a Spinster, but You Develop a New Crush

When It's Thanksgiving and Grandma Starts to Get a Little Insensitive

When You're Trying to Stay in Your Lane and Your Friend Drags You Into a Fight

When You Truly Believe You're a Disney Princess

When Your Friend Has a Meltdown Outside the Club

When Your Roommate Eats Your Leftovers Out of the Fridge

When Your New Acquaintance Offers You the Rest of His Lunch

When You're Ushering a New, Innocent Youth Into Your Jaded Life

When You Encounter a Cat at a House Party

When Your Muffins Aren't a Hit at Your Friend's Potluck Brunch

When Your Friend Takes Your Drunk Ass Home and Tucks You In

When You're Trying to Get a Free Drink From a Group of Guys

When Your Friend Watches Your Favorite Show Without You

When Your Enemy Tells You You're Looking Cute Today

When You Joke About Stealing Your Bestie's Boyfriend

When Your Friend Says They're Sober Enough to Drive Home

When You Still Haven't Let Go of Your Hogwarts Fantasies