I haven't gotten any love or hate mail yet, or coupons, but all the dates my Sims have been on have been dream dates. One night my Sim went on three different dream dates. Two of the dates left flowers on the doorstep at the same time. I expected a fight to break out, but it didn't.
One date brought a §3,500 flat screen TV, and another brought a DJ booth, around §2,750. I kept the TV, sold the DJ booth. One Sim I played got the TV, the other got the booth.
The two dates that left expensive gifts got maxed out date meters, and the dates were still running and still getting points. That might be the trick to getting expensive gifts.
Hook