3¢ George Washington
This “beautiful Valentine use with the first stamp issued in the Western Hemisphere” (Figure 1) showcases the 3¢ black on grayish paper portrait of George Washington used by Greig’s City Despatch Post of New York City, issued February 1, 1842 (Scott 40L1). Mailed two weeks later on February 14, the stamp is tied by the large red circular datestamp with “N.Y.” inverted in use for less than six months before the company was bought by the government, becoming the United States City Despatch Post. 
Figure 1. Lot 2407 of "U.S. Postal History" auction at Siegel Auction Galleries, November 8, 2017. Lot 2407 in the sale, it was estimated at $5,000 to $7,500, but hammered down at $21,000.
1¢ Blue Benjamin Franklin
Benjamin Franklin Bailar, the 64th U.S. Postmaster-General, formed a fantastic collection of stamps, covers and ephemera related to his namesake, the first American Postmaster-General. Among its many highlights offered in the Siegel sale of that collection in 2015 was this beautiful and colorful Romeo and Juliet Valentine in which Shakespeare’s tragic lovers pay tribute to Cupid. An embossed multicolor enclosure featured lovebirds and a label bearing the charming couplet:
You are all my heart’s treasure
My joy and my pleasure.
The connection to Benjamin Franklin is the Valentine’s handsome 1861 1¢ blue Franklin, Scott 63, neatly canceled and tied with a lozenge “PAID” handstamp (Figure 2).
Figure 2. Siegel Auction Galleries 2015. Despite a small tear, the cover estimated at $2,000 to $3,000, sold for $6,750.
2¢ Blue St. Louis Penny Post
A 2002 Rarities of the World auction featured “the most spectacular of the four recorded covers bearing the 1857 2¢ blue St. Louis Penny Post stamp,” Scott 8LB3. This gilt-and-lace Valentine’s cover contained an enclosure with even more elaborate gilt and enamel decoration surrounding the sender’s ardent love poem (Figure 3). The cover is datelined February 13, and addressed to “Mrs. Scoot / Sixth Street above Morgan / Street next door to No. 170 / St Louis / Moissori.”
Figure 3. This cover featured in Siegel Auction Galleries' 2002 Rarieties of the World sale. The cover sold for $32,500.
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Figure 4. The Valentine was estimated at $400 to $500 in a 2015 auction sale, but sold for $200 — almost as though it seemed haunted.
Unclaimed Stampless Cover
Love can have a tragic outcome, as many can testify. Few fates seem sadder than that of this stampless envelope mailed on Valentine’s Day 1851 (noted below the address) from Bristol, Connecticut, to John G. Williams of Utica, New York. The embossed enclosure, signed “Rosamond,” is headed by her sketch of two doves in a tree inscribed “Love,” and what the auctioneer described as “a poignant poem to John about friendships and love dying, including:
A silent smile, a sad goodbye
Forget not her who lonely here
Still prays that bliss may be your lot.
The cover tells the rest of the tale (Figure 4). Never called for by John, the woeful love letter languished, nor did advertising its presence at the post office bring John by. It was unclaimed, a fate we can hope “Rosamond” did not share.
The 1851 1¢ Type 1 and Friends
“The unique use of the 1851 1¢ Type I on a Valentine” was reckoned “one of the greatest postal history rarities of the 1851 issue” in Siegel’s 2013 Rarities of the World sale, combining Scott 5 in a vertical pair with the 1¢ Type IIIA (8A), a 1¢ Type Ib (5A) at the tip of the backflap and three 3¢ brownish carmine Type II (11A) to pay the 12¢ rate on this overweight Valentine’s envelope (with Cupid’s bow and quiver on the backflap) sent six miles in Connecticut.
Siegel reckons the 1851 1¢ Type I as “the rarest of all U.S. stamps issued regularly prior to the 1868 Grills.” Still, for all the expense and extravagance that the sender went to, would the tiny hand-chosen card within the elaborate multicolored Valentine succeed in enraptured the recipient?
The cover, however, is magnificent (Figure 5).
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Figure 5. Siegel Auction Galleries "Rarities of the World" sale, 2013. The cover sold for $50,000.
1847 5¢ Franklin
Not all Valentine’s Cards are created for the newly infatuated, as witness this embossed card sent with an 1847 5¢ Franklin (Figure 6) from Boston to Hubertson, Massachusetts. The mature admission from man to woman is that she is “My Comfort / And My Joy” on a card that doesn’t need a Cupid.
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Figure 6. Sold in Siegel Auction Galleries’ November 2017 sale of "U.S. and C.S.A. Postal History" for $475.
Editor's Note: "Valentines: The Postal History of Love" was originally published in the February 2019 issue of The American Philatelist. To read back issues of The American Philatelist, click here and scroll down to the Back Issues section. Happy Valentine's Day!