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RAW, it's valid if the ranger is strong enough: The push, drag or lift rule.

Thanks to the comments under this answer, I realized that Grappling can be used but doesn't really take into account the fact that the target is willing. Then, I thought: "The Warlock is already as fast as an anchor, what if we stop considering them as a creature and just as loot to transport?". Here comes the "Push, drag or lift rule":

You can push, drag, or lift a weight in pounds up to twice your carrying capacity (or 30 times your Strength score). While pushing or dragging weight in excess of your carrying capacity, your speed drops to 5 feet.

This allows the floating warlock to be pushed around by another character, as long as they are strong enough!

##But I think your first ruling was totally okay

Even if it wasn't RAW, rule of cool totally applies here, I think your ruling was good. This was a great idea and you rolled with it. Great job.

RAW, it's valid if the ranger is strong enough: The push, drag or lift rule.

Thanks to the comments under this answer, I realized that Grappling can be used but doesn't really take into account the fact that the target is willing. Then, I thought: "The Warlock is already as fast as an anchor, what if we stop considering them as a creature and just as loot to transport?". Here comes the "Push, drag or lift rule":

You can push, drag, or lift a weight in pounds up to twice your carrying capacity (or 30 times your Strength score). While pushing or dragging weight in excess of your carrying capacity, your speed drops to 5 feet.

This allows the floating warlock to be pushed around by another character, as long as they are strong enough!

But I think your first ruling was totally okay

Even if it wasn't RAW, rule of cool totally applies here, I think your ruling was good. This was a great idea and you rolled with it. Great job.

RAW, it's valid if the ranger is strong enough  : The push, drag or lift rule.

Thanks to the comments under this answer, I realized that the Grapple can be used but doesn't really take into account the fact that the target is willing. Then, I thought: "The Warlock is already as fast as an anchor, what if we stop considering them as a creature and just as loot to transport?". Here comes the "Push, drag or lift rule"  :

You can push, drag, or lift a weight in pounds up to twice your carrying capacity (or 30 times your Strength score). While pushing or dragging weight in excess of your carrying capacity, your speed drops to 5 feet.

This allows the floating warlock to be pushed around by another character, as long as they are strong enough!

##But I think your first ruling was totally okay

Even if it wasn't RAW, rule of cool totally applies here, I think your ruling was good. This was a great idea and you rolled with it. Great job.

RAW, it's valid if the ranger is strong enough: The push, drag or lift rule.

Thanks to the comments under this answer, I realized that Grappling can be used but doesn't really take into account the fact that the target is willing. Then, I thought: "The Warlock is already as fast as an anchor, what if we stop considering them as a creature and just as loot to transport?". Here comes the "Push, drag or lift rule":

You can push, drag, or lift a weight in pounds up to twice your carrying capacity (or 30 times your Strength score). While pushing or dragging weight in excess of your carrying capacity, your speed drops to 5 feet.

This allows the floating warlock to be pushed around by another character, as long as they are strong enough!

##But I think your first ruling was totally okay

Even if it wasn't RAW, rule of cool totally applies here, I think your ruling was good. This was a great idea and you rolled with it. Great job.

##RAW, the ranger should have been able to pull the warlock only as they were pulling someone grappled

I think you're right about your finding :

• The spell never states the target becomes weightless

• The spell never states anything about somebody else moving the target

• The spell "allows [the target] to move as if it were climbing.", so it still takes the target's movement into account per the rules.

So, technically, for the ranger to pull the warlock, the only rule I can think of is the "move a grappled creature", where the creature can move half of its movement.

##But I think your first ruling was totally okay

Rule of cool totally applies here, I think your ruling was good. This was a great idea and you rolled with it. Still, like every time the rule of cool is invoked, I would warn the players to not try this too often.

Another way to approach this: The push, drag or lift rule.

Thanks to the comments under this answer, I realized that the Grapple can be used but doesn't really take into account the fact that the target is willing. Then, I thought: "The Warlock is already as fast as an anchor, what if we stop considering them as a creature and just as loot to transport?". Here comes the "Push, drag or lift rule" :

You can push, drag, or lift a weight in pounds up to twice your carrying capacity (or 30 times your Strength score). While pushing or dragging weight in excess of your carrying capacity, your speed drops to 5 feet.

This allows the floating warlock to be pushed around by another character, as long as they are strong enough!

RAW, it's valid if the ranger is strong enough : The push, drag or lift rule.

Thanks to the comments under this answer, I realized that the Grapple can be used but doesn't really take into account the fact that the target is willing. Then, I thought: "The Warlock is already as fast as an anchor, what if we stop considering them as a creature and just as loot to transport?". Here comes the "Push, drag or lift rule" :

You can push, drag, or lift a weight in pounds up to twice your carrying capacity (or 30 times your Strength score). While pushing or dragging weight in excess of your carrying capacity, your speed drops to 5 feet.

This allows the floating warlock to be pushed around by another character, as long as they are strong enough!

##But I think your first ruling was totally okay

Even if it wasn't RAW, rule of cool totally applies here, I think your ruling was good. This was a great idea and you rolled with it. Great job.