| 1. |  Bijuu Mike | So i went on a date... | 1,603 | |
| 2. | KPopp | DATING SIM - Fat off Ice Cream! #1 (Deiz Visual Novel/Dating Sim) | 1,239 | |
| 3. | Brysen | Video dates are hard (DOWN BAD) | 1,139 | |
| 4. | KPopp | WTF!! #4 Deiz - Visual Novel/Dating Sim | 713 | |
| 5. | Brysen | video dates are EASY (WE DID IT!!) | 596 | |
| 6. | KPopp | SHE HAS A ****! #5 Deiz - Visual Novel/Dating Sim | 564 | |
| 7. | KPopp | NO LOVE EVER! #7 Deiz - Visual Novel/Dating Sim | 512 | |
| 8. | KPopp | DATING SIM! Man, I Hate that Indie Game #1 | 369 | |
| 9. | KPopp | SURPRISE KISS! #6 Deiz - Visual Novel/Dating Sim | 360 | |
| 10. | KPopp | DAT BOSOM?! #2 (Deiz Visual Novel/Dating Sim) | 323 | |
| 11. | KPopp | FRIENDZONED! #3 (Deiz Visual Novel/Dating Sim) | 230 | |
| 12. | KPopp | Beat Up! - Yume Miru Kusuri A Drug That Makes You Dream (Visual Novel) | 221 | |
| 13. | TreyNotGaming | I Went On Five Dates And Fumbled A Instagram Model... | 44 | |
| 14. | Mamodxx | Tinder Dating Sim?? - Five Dates | 37 | |
| 15. | SuperkenGaming | Five Dates Review [PS4, Switch, Xbox One, & PC] | 33 | Review |
| 16. | KPopp | I TRY ONLINE DATING | what can go wrong??! 👁️👄👁️#datingsim | 29 | |
| 17. | PandaSub2000 | "FIVE DATES" | Part 2: Twerkin' To The Beat Of Love (PandaSub Plays) | 28 | Let's Play |
| 18. | Greyfox Gaming | Five Dates - Full Playthrough | 100% Success Maya | 27 | Let's Play |
| 19. | Reviews 2 Go | Five Dates (Switch) Review | 25 | Review |
| 20. | KPopp | I TRY ONLINE DATING | pt 2 #datingsim | 25 | |
| 21. | Greyfox Gaming | Five Dates - Full Playthrough | 100% Success Paige Lee | 24 | Let's Play |
| 22. | PandaSub2000 | "FIVE DATES" | Part 1: Lookin' For Love In Lockdown! (PandaSub Plays) | 24 | Let's Play |
| 23. | Itz LEGACY | Truth Or Dare With Maya In Five Dates | 22 | |
| 24. | Cheevo Guides | Five Dates - Achievement / Trophy Guide (Xbox) **ALL 6 ENDINGS** | 22 | Guide |
| 25. | David Jaffe | Five Dates (aka Get Sex/Love By Lying To Hot Women) | 21 | |
| 26. | Greyfox Gaming | Five Dates - Full Playthrough | 100% Success Shaina | 18 | Let's Play |
| 27. | Nyanners VODs | Nyanners Plays Five Dates | 18 | |
| 28. | RapidKick Media | Five Dates : YASSS BRUV! - Part 1 - Two Dudes One Couch (Nintendo Switch) | 17 | |
| 29. | Crazy Town Media | Dream Girl | Five Dates (2nd Run) | Ep 5 | Crazy Town Gaming | 17 | Show |
| 30. | ID@Xbox | Five Dates - Reveal Trailer | 15 | Preview |
| 31. | Tongue Tied Games | Searching for My Future X Wife in Five Dates Paige 100% Live Stream Dating Sim | 15 | |
| 32. | Greyfox Gaming | Five Dates - Full Playthrough | 100% Success Grace | 15 | Let's Play |
| 33. | Itz LEGACY | Five dates, im a smooth dude | 13 | |
| 34. | Kanzalone | I Go On Five Dates Digitally During a Pandemic! | 13 | Let's Play |
| 35. | Smexch | Let's Find Us Some Love | Five Dates | 13 | Let's Play |
| 36. | Itz LEGACY | I Met Saffron in Five Dates | 13 | |
| 37. | PandaSub2000 | "FIVE DATES" | Part 3: The Final LoveDown! |Non Interactive Version| (PandaSub Plays) | 13 | Let's Play |
| 38. | Datura Plays | I decided to START DATING so I'm going on FIVE DATES | 13 | |
| 39. | MiniDowgy | Eating Dates Whilst Watching Myself Play Five Dates as I have no bitches | 11 | |
| 40. | HarleyQuinnsMrj | Five Dates: Successful Date With Saffron | 11 | |
| 41. | HarleyQuinnsMrj | Five Dates Maya Happy Ending | 10 | Walkthrough |
| 42. | RapidKick Media | Five Dates : Rusty Nail! - Part 7 - Two Dudes One Couch (Switch) | 10 | |
| 43. | Vicious Fo Life | Love In A Lockdown? | Five Dates Walkthrough Gameplay PS5 Part 1 | 10 | Walkthrough |
| 44. | ZeusyAF | I went on a virtual date with three different girls and heres how it went... | 9 | |
| 45. | The_Littz | LITTZ AND VENTUS TAKE ON A DATING SIMULATOR?! | Five Dates | 9 | |
| 46. | PandaSub2000 | "FIVE DATES" | Part 3: The Final LoveDown! (PandaSub Plays) | 9 | Let's Play |
| 47. | Nerd in the Bay | Returning to the Online Dating Scene w Five Dates Indie Game Stream! | 9 | |
| 48. | iTzjUstSsage | Round 2 in this Dating Game | Dating with Ssage | 8 | |
| 49. | Tongue Tied Games | Making All The Wrong Decisions with Grace in Five Dates Live Stream Dating Sim | 8 | |
| 50. | RapidKick Media | Five Dates : Bit Sweaty INNIT?! - Part 2 - Two Dudes One Couch (Nintendo Switch) | 8 | |
| 51. | Greyfox Gaming | Five Dates - Full Playthrough | 100% Success Saffron | 7 | Let's Play |
| 52. | Nerd in the Bay | Going on Blind Remote Dates for Valentine's Day! Five Dates Indie Game Stream! | 7 | |
| 53. | Nerd in the Bay | Nearing The End of Finding Love w Vinny! Five Dates Indie Game Stream! | 7 | |
| 54. | Yewfieee | 【FIVE DATES】DUMB VTUBER FINDS LOVE | 7 | |
| 55. | RapidKick Media | Five Dates : Bit Cheeky Innit! - Part 6 - Two Dudes One Couch (Switch) | 7 | |
| 56. | BlackGaymerGod | Five Dates (Part 1) | 6 | |
| 57. | FalsLea | Put them grippers away!! #shorts #reaction #gaming #youtubegaming #funny #fivedates #dating | 6 | |
| 58. | RapidKick Media | Five Dates : BUNGLED! - Part 9 - Two Dudes One Couch (Switch) | 6 | |
| 59. | Crazy Town Media | Grace Under Fire | Five Dates (2nd Run) | Ep 2 | Crazy Town Gaming | 6 | Show |
| 60. | RapidKick Media | Five Dates : Big EFFIN' Baby! - Part 4 - Two Dudes One Couch (Switch) | 6 | |
| 61. | RapidKick Media | Five Dates : NOSEDIVE! - Part 5 - Two Dudes One Couch (Switch) | 6 | |
| 62. | Crazy Town Media | Happy Ending | Five Dates | Ep 5 | Crazy Town Gaming | 6 | Show |
| 63. | HarleyQuinnsMrj | Five Dates Game: Successful Date With Shaina | 6 | |
| 64. | RapidKick Media | Five Dates : Never Have I Ever Played Never Have I Ever! - Part 3 - Two Dudes One Couch (Switch) | 5 | |
| 65. | Cupahnoodle VODS | 01-25-2023 - Five Dates Gameplay - Cupahnoodle Twitch Vods | 4 | |
| 66. | Dre The Saint | I FOUND THE LOVE OF MY LIFE! | Five Dates Playthrough Gameplay | 4 | |
| 67. | RapidKick Media | Five Dates : SICK CANS! - Part 8 - Two Dudes One Couch (Switch) | 4 | |
| 68. | MiniDowgy | Playing Five Dates as I have no bitches - Part 1 | 4 | |
| 69. | The_Littz | I WENT BACK FOR SAFFRON! Five Dates Gameplay | 4 | |
| 70. | HarleyQuinnsMrj | Five Dates: Successful Dates With Maya and Grace | 4 | |
| 71. | Mr Gyp | 5 dates (2) | 4 | |
| 72. | RapidKick Media | Five Dates : Dirty Jokes! - Part 13 - Two Dudes One Couch (Switch) | 4 | |
| 73. | Teddy Gamer | | FIVE DATES EP 5 | BUSCANDO EL AMOR! AY DEOS MEO! | 4 | |
| 74. | It's Rich | Quarantine Tinder Dates?! | Five Dates | 4 | |
| 75. | Dee Pressure | FINDING LOVE IN QUARANTINE.... Five Dates | 4 | |
| 76. | Mr Gyp | 5 dates (1) | 4 | |
| 77. | RapidKick Media | Five Dates : MAN THE EFFING DECK! - Part 11 - Two Dudes One Couch (Switch) | 3 | |
| 78. | Nerd in the Bay | Coming in Strapped with Cyphers for Master Meio! Strider 2014 Stream Final Plus Five Dates! | 3 | |
| 79. | Crazy Town Media | Stood Up | Five Dates (2nd Run) | Ep 4 | Crazy Town Gaming | 3 | Show |
| 80. | MGN TV | Five Dates game review - INCEL EDITION with Big C - MGN TV | 3 | Review |
| 81. | Shawn K The King | Five Dates Review / First Impression (Playstation 5) | 3 | Review |
| 82. | The_Littz | Redemption For The Virgins | Five Dates | 3 | |
| 83. | Roachie | I DATED LADY WITH DAUGHTER ONLINE (GONE RIGHT) | 3 | |
| 84. | Yo It’s Frankie B | Five Dates | Online dating simulation - Full Gameplay Part 3 Guessing Game with Maya & Shaina | 3 | |
| 85. | Teddy Gamer | | FIVE DATES EP 3 | BUSCANDO EL AMOR! CITA CON MAYA! | 2 | |
| 86. | Teddy Gamer | | FIVE DATES EP 1 | BUSCANDO EL AMOR! CITA CON PAIGE! | 2 | |
| 87. | JDN | 16 Year Old Goes On E-Date With A 27 Year Old | 2 | |
| 88. | LazayASAP | Rizz God Returns. | 2 | |
| 89. | MetRighteous TV | GOOD OR BAD ENDING? FINAL DATE WITH SAFFRON - Five Dates Gameplay | 2 | |
| 90. | Yo It’s Frankie B | Five Dates | Online dating simulation - Full Gameplay Part 1 First Time Online Dating | 2 | |
| 91. | VOKIEO | I Put My Good Mans Onto This Bad Jawn And He... (FIVE DATES) | 2 | |
| 92. | MiniDowgy | Playing Five Dates as I have no bitches - Part 3 (Final) | 2 | |
| 93. | RapidKick Media | Five Dates : Truly Madly Lonely! - Part 10 - Two Dudes One Couch (Switch) | 2 | |
| 94. | Yewfieee | WEIRDEST DATING SIM | VTUBER #shorts | 2 | |
| 95. | minakatajeffu | Oh man! i miss dating and falling in LOVE! [Five Dates] | 2 | |
| 96. | HarleyQuinnsMrj | Five Dates: Successful Date With Paige | 2 | |
| 97. | richie n' beeto | everytime this game is cringe, the video gets faster | Five Dates | 2 | |
| 98. | Yo It’s Frankie B | Five Dates | Online dating simulation - Full Gameplay Part 4 Our Last Date | 2 | |
| 99. | Yorkie Plays | ChatGPT Plays Five Dates, pt 4 | 2 | Let's Play |
| 100. | Yorkie Plays | Five Dates, pt 1 Love Online | 2 | |
