I agree with dating from GTA: San Andreas. It was pointless and tedious IMO and offered nothing that was very beneficial for the player. This, as well as fact that the protagonist had to eat once in a while or else he would "become hungry" - it doesn't count as a side mission or a minigame; but I hated it nonetheless and how it was somewhat forced upon the player and thus was annoying as a result. Thankfully, it was never reintroduced in GTA titles following.
Ambulance missions in all of the 3D era GTA titles were also tedious and repetitive; and for very little reward for completing them other then a boost to your max health. Likewise with firefighting.
Friendships in GTA IV, IMO, weren't as bad as dating was in GTA: San Andreas as they at least offered proper reward for your effort - for example, being able to call Little Jacob so you can buy weapons and ammunition on the go when the player reaches a certain percentage with him, or being able to use Packie to set up car bombs, Dwayne's backup, etc. The friendship system in GTA V is more pointless, however, as it offered no reward or incentive what so ever.