Lorelai claims that she’s helping Emily pick out the “perfect present” for Rory during their joint shopping trip. Given how expensive her own gift to Rory is, does anyone else think that Lorelai is actually (consciously or unconsciously) sabotaging Emily’s gift-buying so that she can’t compete with Lorelai? Instead of something valuable, she ends up with a cheap, tacky name bracelet that doesn’t really seem like something Rory would appreciate.
On the other hand, the bracelet does seem like something Lorelai would have liked as a teenager. The shopping trip becomes the kind of outing that she and her mother might have learned to enjoy together if Lorelai hadn’t got pregnant. Through it she can vicariously experience what it would have been like to have her mother buy her the things that she valued, such as junk jewellery and celebrity tee-shirts, instead of the pearls and cashmere that Emily would have given her as suitable gifts for a young girl of good family.
It is another sign of Lorelai’s immaturity and ego, and also how deep down she still longs for a relationship with her mother. If not deliberate sabotage, it’s a hint that she may not know Rory as well as she thinks she does.
The Annotated Gilmore Girls 