| 1. |  Derek Fischer (Hiddeninplainview) | 6:53:35 | Five Dates: Crash and Burn | 36:11 |
| 2. | Tane Tenshi | 5:24:36 | (VoD) EVIL SENSEI - Monster Girl is Happy💕 [Five Dates Gameplay] | 5:24:36 |
| 3. | eem supreme | 5:19:37 | Five Dates | Shaina | Walkthrough + Live Commentary | Xbox Series X [4Kp60] | 1:14:03 |
| 4. | Longplay Universe | 5:15:06 | Five Dates (All Achievements) | Series X | Longplay | Walkthrough #3 [4Kp60] | 5:15:06 |
| 5. | Enna Alouette【NIJISANJI EN】 | 5:04:03 | 【FIVE DATES】😳😳😳【NIJISANJI EN | Enna Alouette】 | 5:04:03 |
| 6. | Fallon Bowman Twitch VODs | 4:38:01 | all the girls love me now - FIVE DATES PLAYTHROUGH pt.2 | Fallon Bowman Twitch | 2:12:40 |
| 7. | Vesever | 3:49:58 | Five Dates - Twitch Stream | 3:49:58 |
| 8. | Pharaoh TV | 3:12:18 | Five Dates - Ummmmm.... Let's See what happens!! | 3:12:18 |
| 9. | xQc | 2:12:24 | Trying to find the Juice with online dating... (Five Dates) | 2:12:24 |
| 10. | Kroden | 1:59:15 | Five Dates to be the worst partner | 1:59:15 |
| 11. | Millymazilla | 1:42:01 | Couple Goes on Blind Date together | Five Dates Rom-Com Game #romanticcomedy | 1:41:17 |
| 12. | The Gamer's Grotto | 1:41:25 | Five Dates -- FMV game (PS4) | 1:41:25 |
| 13. | The Six Clips | 1:32:11 | How Not To Date - Five Dates - Interactive Movie | 1:14:37 |
| 14. | Pokelawls | 1:28:24 | We tried an online dating game... | 1:28:24 |
| 15. | Kloud Rebirth | 1:27:26 | Kloud Plays FiveDates | 1:27:26 |
| 16. | Mineic | 1:01:21 | YOU MISS EVERY SHOT YOU DON'T TAKE!! | Five Dates #3 | 23:04 |
| 17. | Jon Renish | 47:13 | Steam Cleaning - Five Dates | 47:13 |
| 18. | Library Gamer | 21:55 | FIVE DATES Citas en tiempos de pandemia... | 21:55 |
| 19. | jmarshhh | 4:29 | Trying Out Online Dating | Previously On (February 02 2021) | 4:29 |
| 20. | YourGibs Gaming | 0:00 | Five Dates (FMV) Dating Sim - Full Game Walkthrough No Commentary with Endings | 0:00 |
