Smalltalk, a dynamically typed object oriented programming language
Small Talk, the first sound film in the Our Gang (Little Rascals) short subjects series, released in May 1929.
Small Talk (album), a 1974 album by Sly & the Family Stone, the final LP to feature the original Family Stone
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Smalltalk lets you and your interlocutor take little steps until you find ground you share.
(If it expresses something small in something big, you leave during the intermission.) Likewise, in smalltalk, we express ourselves in the details of what we talk about, the words we use, the ones we don't, how far we lean forward, how tentatively or aggressively we probe for shared ground.
While talking about replacing Microsoft products: I've been using Mozilla Thunderbird instead of Outlook for the past few months and it is a solid, delightful, free, open source product.