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ABC Chinese–English Comprehensive Dictionary (2003). I can't access the "slightly revised through July 2005" ed.

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  1. The 搭 in 搭訕 doesn't make sense to me. 搭 doesn't mean 'strike up' or 'reply'.

  2. What exactly does 訕 mean? The embarrassing context?

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From Zdic (汉典), has also the meaning of "to come into contact, to meet":

  1. 交接,配合:~配。~伙。~档。~售。~伴。~帮。~腔。~话。~界。~讪

The last one in the above entry is exactly the example of 搭讪.

The same dictionary provides an entry for 讪 (but also MDGB does), where it's shown that 讪 alone means "to mock, to ridicule".

So 搭讪 together is somewhat an extension of the two meanings of 搭 and 讪, like to meet a mocking (meet = counter). MDGB again gives "to end an embarrassing silence by striking up a conversation", and Zdic "勉强找话说以消除尴尬".


PS: I vividly suggest you include Zdic in your preferred vocabulary sources. Even though the interface is in Chinese, you can easily copy-paste characters in the search bar and get decent results.

PS 2: I'm not sure why you think that words composed of 2+ characters must absolutely reflect preexisting meanings of the single characters. Languages can be productive.

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    Thanks. "I'm not sure why you think that words composed of 2+ characters must absolutely reflect preexisting meanings of the single characters. Languages can be productive." I don't think this. You're correct. I just have difficulty with semantic shifts.
    – user11787
    Sep 13, 2020 at 21:13

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