I like to choose stamps for franking that match the occasion, the card design, the interests of the recipient, or some combination of those.
Christmas stamps, wedding invitations, etc. are such simple examples as to not really be worth mentioning.
Not long ago I used an Athens Olympics runner stamp and a black cat Pets stamp (with another 3c to make up the rate at the time) to someone who lives in Athens, Georgia and is a dedicated runner with a pet black cat.
I noticed a buyer on ebay was buying a whole bunch of space covers so I franked his envelope with only space stamps. Perhaps he liked the personal touch
once on a letter to a friend who is a Neil Young fan, I used a combo of 20 cent American Dogs amd 20 cent Balloons, but I do not know if he realized those were "the barkers and the colored balloons"
I've been using up a stock of old 60 cent stamps in the last few months. Now that first class is up to 63 cents, I have been adding 3 cent stamps from back in the 30s, 40s and 50s remaining from an old cannibalized album. So the flag raising on Iwo Jima went to an ex-marine, a California statehood to a Californian, Baseball centennial to my dentist who loves the game, etc. The Marine noticed to be sure!
I collect pictorial postmarks, as listed in the Postal Bulletins every two weeks. I always try to find a stamp that matches at least the concept of the cancel being used, which is tough to do with the latest forever stamps. For example, the current batch available has two for the McKinley Exhibition Center. One shows a football, the other a doghouse. What better stamps to choose for those than Charlie Brown or Lucy for the football and Snoopy for the doghouse?
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