Depends how good your mortar is. It does tend to crumble if it's not very strong so it's probably worth going into the brick. Hanging baskets weigh a lot so a good fixing is essential. (Yes, I've had one come out the wall!! - Bitter experience!!)
Depends how big/heavy the basket is too. But I've always put mine into the brick, or wherever possible - somewhere that doesn't require drilling into my house. If the mortar's quite old, they can gradually work their way out and before you know it, plants all over the path!
We've got a nice pergola and they hang quite nicely on the wooden frame.
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