I cannot take a grown man >30 on a skateboard seriously and I believe most women would see such a man as a cheap retard stuck in boyhood.
Instead of a skateboard try motorbike. Less skill an training needed, plus you can actually take girls for a ride. You will need more money trough but common skateboarding is too cheap, it's for children.
If you want to attach success with women with a proficiency at any tool then two most time tested tools are motorbikes and guitars. Master either one and you will have some girl even if you are relatively game-less. But of course you don't really need tools, you need game first and foremost.
Instead of a skateboard try motorbike. Less skill an training needed, plus you can actually take girls for a ride. You will need more money trough but common skateboarding is too cheap, it's for children.
If you want to attach success with women with a proficiency at any tool then two most time tested tools are motorbikes and guitars. Master either one and you will have some girl even if you are relatively game-less. But of course you don't really need tools, you need game first and foremost.