The two candies most associated with Valentines Day in America are Conversation Hearts and chocolate. Fancy heart-shaped packaging, like Valentines cards, evolved from Victorian traditions.

Conversation hearts
Converation Hearts, as we Americans know them today, descended from British Conversation Lozenges and Motto Rocks. These have been popular confections from the mid-19th century forwards. In older times words were sometimes imprinted by molds or inserted (paper) into the confection.

"Kissing comfits , as detailed by Robert May in 1685, were sugar paste containg musk, civet, ambergris, and orris powder. These were printed in moulds or rolled into little pellets and then squeezed flat with a seal...The combination of sugar and mottoes continued, Hannah Glasse gave instructions 'to make little things of sugar, with devices in them. These were made from the pieces of sugar paste, tinted whatever colour was preferred, 'in what shapes you like...in the middle of them have little pieces of paper, with some pretty smart sentences wrote on them; they will in company make much mirth.' But the writing migrated from paper to the sweet itself with the Victorian fashion for 'conversation lozenges'. Those who were tongue-tied could always offer their companion a little piece of sugar paste printed with some suitable inscription. 'How do you flirt?' "Can you polka?' and 'Love me' were amongst those available from Terry's in York; for those wanting to make a really positive response, a large medallion moulded with a heart and the words 'I will' was available. Another novelty was reminiscent of Hannah Glasse's little things with devices in them. As advertised by the firm of Thomas Handisyde in the East End of London, these were 'Handisydes Secret Charms suck carefully and the secret message will appear'. Handisyde produced various shapes and sizes of conversation lozenges, the larger ones cut in hearts, circles, and elegant oblongs with ogee edges. The temperance movement used the idea of motto lozenges to promote their message. 'Drink is the ruin of man'...The inscriptions were added to the sweets by printing the tops with stamps dipped in dyes."
---Sugar Plums and Sherbet: The Preshistory of Sweets, Laura Mason [Prospect Books:Devon] 2004 (p. 146-147)

Why do we give chocolate on Valentine's Day?
Some folks believe chocolate is given because it's an aphrodesiac. Cadbury's is often cited as one of the first companies to promote this holiday practice. About chocolate

Confectionery historians confirm special packaging has been employed for candy for hundreds of years. The earliest reference we find in American print to Valentine's Day confections packed in fancy heart-shaped boxes is from the 1890s:

"Among the sweetest valentines seen were those designed by the confectioners. Some shown in beautiful glass-covered boxes were heart shape, the foundation being a layer of pale pink cream confectionery, half an inch thick, edged all around with candied rose leaves in clusters to represent tiny roses. Included in this flowery frame was a smaller heart formed of a solid mass of the rose leaves, and surrounding it were the words, in raised letters, covered with gold leaf, "For my valentine." The box, into which the lovely confection exactly fitted, was of pink satin, the rim around the glass top being covered with a narrow row of finely-plaited pink silk net. In this dainty casket the valentine can be preserved for generations, if so desired, or, if consumed, the case will serve as a charming receptable for jewels. Others, similary designed, were of candied violets, in violet satin boxes. An exquisitely delicate one, that shows the confectioner's art in its highest development, resembled a delicate bisque piece in coloring and finish. In the centre of a square of lemon-colored cream, bordered with ale green primroses, were two figures, one of a bewitching little girl in a Greenaway gown and a huge hat loaded with white ostrich tips, and the other a boy in a picturesuqe Continental suit, standing before her, cocked hat in hand, in the act of making an elaborate bow. The faces and dresses are wonderfully well done, and every particle of the whole is composed of the very choicest candy. On the right, in gold letters, are the words, "Will you be my valentine?" Their values range from $5 upward, including box, those with the figures being, of course, higher priced than th others and they make a far more sensible gift than gold-plated bonbons at $40 a pound, which are a caprice just now with the ultra fashionables." ---"In Honor of St. Valentine," New York Times, February 4, 1894 (p. 18)

"Valentine Candy Boxes---All in heart shape, in numerous pretty colored designs. Filled with chocolate drops. Were 40 cents each, now 25 cents."---Display ad, John Wanamaker's, New York Times, February 12, 1901 (p. 4)

The Cadbury connection?

"The tradition of giving chocolates on Valentine's Day can be traced to Richard Cadbury, of the English chocolate-making family, who "invented" the first Valentine's Day candy box during the Victorian era. The Victorians, who fancied decorating cards with plump cupids shooting arrows of love, later transferred the image to the lids of heart-shaped boxes filled with dreamy combinations of silken chocolates."
---"For Lovers, Chocolate," Niki Dwyer, The Buffalo News, February 11, 1998, Lifestyles (p. 2D)

Cadbury itself acknowledges making fancy boxes of chocolates, though it stakes no claims on Valentine's Day:

"Cadbury's 'fancy chocolates' (or assortments) were sold in decorated boxes with small pictures that children could cut out to stick into scrapbooks. Richard Cadbury, who had considerable artistic talents, set out to introduce more ambitious and attractive designs from his own paintings: many of his original boxes still exist. Using his own children as models, or depicting flowers and scenes from holiday journeys, he introduced the first British made fancy chocolate boxes. These proved to be popular, helping both the Cadbury business and the confectionery trade in general. Elaborate chocolate boxes were prized by the late Victorians as special gifts, to be used as trinket or button boxes once the fancy chocolates had been eaten: designs therefore had after-use very much in mind. Designs ranged from superb velvet covered caskets with bevelled mirrors and silk lined jewel boxes, to pretty boxes with pictures of kittens, landscapes or attractive girls on the lid. Their popularity continued until their disappearance during the 1939-45 war: Victorian and Edwardian chocolate boxes are now treasured collectors' items. In the 1870s the quality of the chocolates produced by the company following the introduction of the cocoa press helped Cadbury break the monopoly French producers previously enjoyed in the British market."
SOURCE: Cadbury

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Research conducted by Lynne Olver, editor The Food Timeline. About this site.