Flirting Videos and Pictures - Featured

- Featured 07/06/2022
- Dudes Trying to Flirt through Roleplay Is New Level Cringe
- What dude thought this was a good way to flirt with someone?
- zachnading
  Uploaded 07/05/2022 in creepy
- - 13.7k Views
  - 2 Comments
  - 0 Favorites
- Featured 03/16/2022
- 25 Pieces of Advice We Wish We Could Give Our Teenage Selves
- They say hindsight is always 20/20. And that's especially true when it comes to our teenage memories.
- PocketEpiphany
  Uploaded 03/16/2022 in feels
- - 15.6k Views
  - 2 Comments
  - 0 Favorites
- Featured 06/15/2022
- 69 Cringy Pick Up Lines So Bad, They're Good
- When it comes to pick-up lines, nothing ventured, nothing gained I say.
- damn_nation_inc
  Uploaded 10/27/2021 in Funny
- - 14.2k Views
  - 6 Comments
  - 0 Favorites
- Featured 10/03/2021
- Jaguars HC Urban Meyer Caught Mackin' on Cuties After Loss
- After suffering a loss to the Cincinnati Bengals this past Thursday, Jacksonville Jaguars coach Urban Meyer apparently decided to stay behind in his...
- SKYBRITE
  Uploaded 10/03/2021 in facepalm
- - 22.4k Views
  - 4 Comments
  - 0 Favorites
- Featured 08/19/2020
- 'Unattractive' Features That Ladies Actually Find Very Attractive
- Pay attention, fellas!
- damn_nation_inc
  Uploaded 08/18/2020 in feels
- - 32.1k Views
  - 9 Comments
  - 0 Favorites
- Featured 05/08/2020
- Oblivious Guys Share the Dumbest Ways They've Turned Girls Down Without Knowing It
- At least I know I'm not alone.
- damn_nation_inc
  Uploaded 05/05/2020 in facepalm
- - 17.6k Views
  - 5 Comments
  - 0 Favorites
- Featured 04/03/2021
- Guy Tells Cringelord Friend "She's Not Gonna F*** You" in Group Chat
- Some folks say he went too far, while others see nothing wrong with what he did.
- damn_nation_inc
  Uploaded 05/05/2020 in Funny
- - 161k Views
  - 22 Comments
  - 0 Favorites
- Featured 11/16/2019
- Hitting on Girls with Flirting Advice They Just Gave
- ... Did he just crack the code?
- damn_nation_inc
  Uploaded 11/15/2019 in Funny
- - 15.2k Views
  - 14 Comments
  - 0 Favorites
- Featured 11/06/2019
- Witness the Exact Moment This Wannabe Romeo's Soul is Crushed
- They say you miss 100% of the shots you don't take, but this guy's attempt couldn't even hit the broad side of a barn.
- kilgore9012
  Uploaded 11/05/2019 in Funny
- - 34.6k Views
  - 13 Comments
  - 1 Favorites
- Featured 10/03/2019
- Drive-Thru Employee Enjoys a Romantic Moment as Cars Line up Waiting
- When all you wanted to do was to order food, but you've interrupted an employee's date.
- BrandAid
  Uploaded 10/02/2019 in facepalm
- - 17.5k Views
  - 28 Comments
  - 0 Favorites
- Featured 05/19/2019
- Uber Driver Faces Endless Advances from Drunk Ladies
- Is this what it's like to be attractive?
- CoolAndFun
  Uploaded 05/19/2019 in facepalm
- - 47k Views
  - 13 Comments
  - 0 Favorites
- Featured 08/18/2017
- 17 Of The Worst Attempts At Flirting Women Have Ever Received
- C'mon bros, you gotta try harder than that.
- solidsnake4545
  Uploaded 08/18/2017 in facepalm
- - 48k Views
  - 3 Comments
  - 0 Favorites
- Featured 03/13/2017
- Couple Of Secret Lovebirds Get Caught At 50,000 Feet
- Their magical moment together gets exposed by a stewardess.
- kilgore9012
  Uploaded 03/12/2017 in feels
- - 52.1k Views
  - 3 Comments
  - 0 Favorites
- Featured 02/25/2016
- Cheating Husband Ambushed by Wife & Best Friend
- Husband caught messing around.
- jihadpizza
  Uploaded 02/20/2016 in Funny
- - 158k Views
  - 66 Comments
  - 3 Favorites
- Featured 04/12/2015
- 23 People Who Are Totally Nailing This Flirting Thing
- To some people texting is like sculpting a masterpiece.
- solidsnake4545
  Uploaded 04/11/2015 in Funny
- - 114k Views
  - 24 Comments
  - 10 Favorites
- Featured 09/15/2014
- Homeless Guy Survives By Picking Up Women Every Night
- Surviving by panhandling and an incredible knack for picking up women.
- PepperPeanut
  Uploaded 09/15/2014
- - 448k Views
  - 65 Comments
  - 12 Favorites
- Featured 07/09/2011
- Drive Thru Flirting Goes Wrong
- I'm no detective, but I think "SHE" was at the window..
- nyyank257
  Uploaded 07/07/2011
- - 103k Views
  - 392 Comments
  - 18 Favorites
- Featured 08/02/2009
- Guy Flirting on the News
- Guy uses his platform to hit on the hot reporter
- fetismo
  Uploaded 07/30/2009
- - 72.4k Views
  - 775 Comments
  - 5 Favorites
- Featured 12/26/2008
- Magic Dating
- It would certainly be one heck of a magic trick if this actually helped you with the ladies.
- berv
  Uploaded 12/22/2008
- - 40.2k Views
  - 300 Comments
  - 11 Favorites

15 Life Hacks That Are Actually Pretty Good

Giselle Posts 'Cold' Comment on Tom Brady's Retirement Post

37 Magical Memes Conjured Up in the Dank Dungeon

Elderly Man Working Out Catches the Ire of an Entitled Influencer

47 Dank Memes Hand Selected For You

TAGGED FLIRTING - FEATURED

Dudes Trying to Flirt through Roleplay Is New Level Cringe

25 Pieces of Advice We Wish We Could Give Our Teenage Selves

69 Cringy Pick Up Lines So Bad, They're Good

Jaguars HC Urban Meyer Caught Mackin' on Cuties After Loss

'Unattractive' Features That Ladies Actually Find Very Attractive

Oblivious Guys Share the Dumbest Ways They've Turned Girls Down Without Knowing It

Guy Tells Cringelord Friend "She's Not Gonna F*** You" in Group Chat

Hitting on Girls with Flirting Advice They Just Gave

Witness the Exact Moment This Wannabe Romeo's Soul is Crushed

Drive-Thru Employee Enjoys a Romantic Moment as Cars Line up Waiting

Uber Driver Faces Endless Advances from Drunk Ladies

17 Of The Worst Attempts At Flirting Women Have Ever Received

Couple Of Secret Lovebirds Get Caught At 50,000 Feet

Cheating Husband Ambushed by Wife & Best Friend

23 People Who Are Totally Nailing This Flirting Thing

Homeless Guy Survives By Picking Up Women Every Night

Drive Thru Flirting Goes Wrong

Guy Flirting on the News

Magic Dating

Follow us on Instagram

Top 5

Contest

Get our free newsletter

Amazing new updates!